Molecular Variations Based on Isosteric Replacements

The Practice of Medicinal Chemistry

Volumn , Issue , 2008, Pages 290-342

  Ciapetti, Paola ^a   Giethlen, Bruno ^b  

^a Novalyst Discovery   (France)

^b Prestwick Chemical Inc   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882506696     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-374194-3.00015-9     Document Type: Chapter

References (257)

1. Langmuir I. The structure of atoms and the octet theory of valence. Proc. Natl. Acad. Sci. USA 1919, 5(7):252-259.
2. Friedman H.L. Influence of isosteric replacements upon biological activity. NASNRS 1951, 206:295-358.
3. H.S. Allen, Molecular Frequency and Molecular Number. London, 1918; Vol. parts I-III.
4. Langmuir I. Isomorphism, isosterism and covalence. J. Amer. Chem. Soc. 1919, 41:1543-1559.
5. Patani G.A., LaVoie E.J. Bioisosterism: a rational approach in drug design. Chem. Rev. 1996, 96(8):3147-3176.
6. Seifriz W. Pathogenicity and isosterism. Science 1948, 107:15-16.
7. Grimm H.G. Structure and size of the non-metallic hybrids. Z. Electrochem. 1925, 31:474-480.
8. Grimm H.G. On the systematic arrangement of chemical compounds from the perspective of research on atomic composition; and on some challenges in experimental chemistry. Naturwissenschaften 1928, 17:557-564.
9. Erlenmeyer H., Leo M. On pseudoatoms. Helv. Chim. Acta. 1932, 15:1171-1186.
10. Gelmboldt V.O., Ennan A.A., Ganin E.V., Simonov Y.A., Fonari M.S., Botoshansky M.M. Synthesis and structure of fluorosilicic acid compounds with 4-aminobenzoic acid and with 4-aminobenzenesulfonamide: the role of H-bonding in crystal structure formation. J. Fluorine Chem. 2004, 125:1951-1957.
11. McLeod J.W., Mayr-Harting A., Walker N. Observations on the bactericidal and bacteriostatic actions of p-aminobenzenesulfonamide and p-hydroxylaminobenzenesulfonamide, with special reference to their suppression by p-aminobenzoic acid. Br. J. Exp. Pathol. 1944, 25:27-37.
12. Brauner-Osborne H., Krogsgaard-Larsen P. Pharmacology of (S)-homoquisqualic acid and (S)-2-amino-5-phosphonopentanoic acid [(S)-AP5] at cloned metabotropic glutamate receptors. Br. J. Pharmacol. 1998, 123(2):269-274.
13. Malachowski W.P., Coward J.K. The chemistry of phosphapeptides: investigations on the synthesis of phosphonamide, phosphonate, and phsophinateanalogues of glutamyl-γ-glutamate. J. Org. Chem. 1994, 59(25):7625-7634.
14. Thornber C.W. Isosterism and molecular modification in drug design. Chem. Soc. Rev. 1957, 8:563-580.
15. Burger A. Medicinal Chemistry 1970, 64-80. Wiley-Interscience ed., New York. 3rd ed.
16. Lima L.M., Barreiro E.J. Bioisosterism: a useful strategy for molecular modification and drug design. Curr. Med. Chem. 2005, 12(1):23-49.
17. Janssen P.A.J., Van der Eycken C.A.M. The chemical anatomy of potent morphine-like analgesics (p. 42). Drugs Affecting the Central Nervous system 1968, 25-60. Marcel Dekker, Inc., New York. A. Burger (Ed.).
18. Boyle E.A., Mangan F.R., Markwell R.E., Smith S.A., Thomson M.J., Ward R.W., Wyman P.A. 7-Aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids as analgesic agents. J. Med. Chem. 1986, 29:894-898.
19. Morgan B.P., Scholtz J.M., Ballinger M.D., Zipkin I.D., Bartlett P.A. Differential binding energy: a detailed evaluation of the influence of hydrogen bonding and hydrophobic groups on the inhibition of thermolysin by phosphorous-containing inhibitors. J. Am. Chem. Soc. 1991, 113:297-307.
20. Chen Y.L., Nielsen J., Hedberg K.D., Dunaiskis A., Jones S., Russo L., Johnson J., Ives J., Liston D. Syntheses, resolution, and structure-activity relationships of potent acetylcholinesterase inhibitors: 898-carbaphysostigmine analogues. J. Med. Chem. 1992, 35:1429-1434.
21. Marseigne I., Roques B.P. Synthesis of new amino-acids mimicking sulfated and phosphorylated tyrosine residues. J. Org. Chem. 1988, 53:3621-3624.
22. Burke T.R., Smyth M., Nomizu M., Otaka A., Roller P.P. Preparation of fluoro- and hydroxy-4-phosphonomethyl-d,l-phenylalanine suitably protected for solid phase synthesis of peptides containing hydrolytically stable analogues of O-phosphotyrosine. J. Org. Chem. 1993, 58:1336-1340.
23. Erlenmeyer H., Willi E. Zusammenhänge zwischen Konstitution und Wirkung bei Pyrazolonderivaten. Helv. Chim. Acta. 1935, 18:740-743.
24. Wallace E.M., Moliterni J.A., Moskal M.A., Neubert A.D., Marcopoulos N., Stamford L.B., Trapani A.J., Savage P., Chou M., Jeng A.Y. Design and synthesis of potent selective inhibitors of endothelin-converting enzyme. J. Med. Chem. 1998, 41:1513-1523.
25. De Lombaert, S., Stamford, L. B., Blanchard, L., Tan, J., Hoyer, D., Diefenbacher, C. G., Wei, D., Wallace, E. M., Moskal, M. A., Savage, P., Jeng, A. Y. Potent non-peptidic dual inhibitors of endothelin-converting enzyme and neutral endopeptidase 24.11. Bioorg. Med. Chem. Lett. 1997, 7, 1059-1064.
26. Binder D., Noe C.R., Holzer W., Baumann K. Thiophen als Strukturelement Physiologisch Aktiver Substanzen, 16. Thienoisoxazole Durch Substitution am Oximstickstoff. Arch. Pharm. 1987, 320:837-843.
27. Uno H., Kurokawa M., Masuda Y., Nishimura H. Studies on 3-substituted 1,2-benzisoxazole derivatives. 6. Syntheses of 3-(sulfamoylmethyl)-1,2-benzisoxazole derivatives and their anticonvulsant activities. J. Med. Chem. 1979, 22:180-183.
28. Garvey D.S., Wasicak J.T., Decker M.W., Brioni J.D., Buckley M.J., Sullivan J.P., Carrera G.M., Holladay M.W., Arneric S.P., Williams M. Novel isoxazoles which interact with brain cholinergic channel receptors have intrinsic cognitive enhancing and anxiolytic activities. J. Med. Chem. 1994, 37(8):1055-1059.
29. Garvey D.S., Wasicak J.T., Elliott R.L., Lebold S.A., Hettinger A.M., Carrera G.M., Lin N.H., He Y., Holladay M.W., Anderson D.J., et al. Ligands for brain cholinergic channel receptors: synthesis and in vitro characterization of novel isoxazoles and isothiazoles as bioisosteric replacements for the pyridine ring in nicotine. J. Med. Chem. 1994, 37(26):4455-4463.
30. Olesen P.H., Tonder J.E., Hansen J.B., Hansen H.C., Rimvall K. Bioisosteric replacement strategy for the synthesis of 1-azacyclic compounds with high affinity for the central nicotinic cholinergic receptors. Bioorg. Med. Chem. 2000, 8(6):1443-1450.
31. Gohlke H., Gundisch D., Schwarz S., Seitz G., Tilotta M.C., Wegge T. Synthesis and nicotinic binding studies on enantiopure diazine analogues of the novel (2-chloro-5-pyridyl)-9-azabicyclo[4.2.1]non-2-ene UB-165. J. Med. Chem. 2002, 45(5):1064-1072.
32. Heinisch G., Holzer W., Kunz F., Langer T., Lukavsky P., Pechlaner C., Weissenberger H. On the bioisosteric potential of diazines: diazine analogues of the combined thromboxane A2 receptor antagonist and synthetase inhibitor ridogrel. J. Med. Chem. 1996, 39(20):4058-4064.
33. Haginoya N., Kobayashi S., Komoriya S., Yoshino T., Suzuki M., Shimada T., Watanabe K., Hirokawa Y., Furugori T., Nagahara T. Synthesis and conformational analysis of a non-amidine factor Xa inhibitor that incorporates 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine as S4 binding element. J. Med. Chem. 2004, 47(21):5167-5182.
34. Wood M.R., Schirripa K.M., Kim J.J., Wan B.L., Murphy K.L., Ransom R.W., Chang R.S., Tang C., Prueksaritanont T., Detwiler T.J., Hettrick L.A., Landis E.R., Leonard Y.M., Krueger J.A., Lewis S.D., Pettibone D.J., Freidinger R.M., Bock M.G. Cyclopropylamino acid amide as a pharmacophoric replacement for 2,3-diaminopyridine. Application to the design of novel bradykinin B1 receptor antagonists. J. Med. Chem. 2006, 49(4):1231-1234.
35. Abe Y., Kayakiri H., Satoh S., Inoue T., Sawada Y., Inamura N., Asano M., Aramori I., Hatori C., Sawai H., Oku T., Tanaka H. A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 3. Discovering bioisosteres of the imidazo[1,2-a] pyridine moiety. J. Med. Chem. 1998, 41(21):4062-4079.
36. Contreras J.M., Parrot I., Sippl W., Rival Y.M., Wermuth C.G. Design, synthesis, and structure-activity relationships of a series of 3-[2-(1-benzylpiperidin-4-yl)ethylamino]pyridazine derivatives as acetylcholinesterase inhibitors. J. Med. Chem. 2001, 44(17):2707-2718.
37. Contreras J.M., Rival Y.M., Chayer S., Bourguignon J.J., Wermuth C.G. Aminopyridazines as acetylcholinesterase inhibitors. J. Med. Chem. 1999, 42(4):730-741.
38. Wermuth C.G. The Practice of Medicinal Chemistry 2003, Academic Press, London, p. 768. 2nd ed.
39. Biava M., Porretta G.C., Cappelli A., Vomero S., Manetti F., Botta M., Sautebin L., Rossi A., Makovec F., Anzini M. 1,5-Diarylpyrrole-3-acetic acids and esters as novel classes of potent and highly selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2005, 48(9):3428-3432.
40. Barbachyn M.R., Ford C.W. Oxazolidinone structure-activity relationships leading to linezolid. Angew. Chem. Int. Ed. Engl. 2003, 42(18):2010-2023.
41. Renslo A.R., Luehr G.W., Gordeev M.F. Recent developments in the identification of novel oxazolidinone antibacterial agents. Bioorg. Med. Chem. 2006, 14(12):4227-4240.
42. Nilius A.M. Have the oxazolidinones lived up to their billing? Future perspectives for this antibacterial class. Curr. Opin. Investig. Drugs 2003, 4(2):149-155.
43. Snyder L.B., Meng Z., Mate R., D'Andrea S.V., Marinier A., Quesnelle C.A., Gill P., DenBleyker K.L., Fung-Tomc J.C., Frosco M., Martel A., Barrett J.F., Bronson J.J. Discovery of isoxazolinone antibacterial agents. Nitrogen as a replacement for the stereogenic center found in oxazolidinone antibacterials. Bioorg. Med. Chem. Lett. 2004, 14(18):4735-4739.
44. 2-receptor histamine antagonists. Medicinal Chemistry: The Role of Organic Chemistry in Drug Research 1993, 227-255. Academic Press, London. C.R. Ganellin, S.M. Roberts (Eds.).
45. Mallamo J.P., Pilling G.M., Wetzel J.R., Kowalczik P.J., Bell M.R., Kullnig R.K., Batzold F.H., Juniewiecz P.E., Winnecker R.C., Luss H.R. Antiandrogenic steroidal sulfonyl heterocycles. Utility of electrostatic complementarity in defining bioisosteric sulfonyl heterocycles. J. Med. Chem. 1992, 35:1663-1670.
46. 3 receptor. J. Med. Chem. 1987, 30:1535-1537.
47. Mathes B.M., Hudziak K.J., Schaus J.M., Xu Y.C., Nelson D.L., Wainscott D.B., Nutter S.E., Gough W.H., Branchek T.A., Zgombick J.M., Filla S.A. Substituted furo[3,2-b]pyridines: novel bioisosteres of 5-HT 1F receptor agonists. Bioorg. Med. Chem. Lett. 2004, 14(1):167-170.
48. Blair J.B., Marona-Lewicka D., Kanthasamy A., Lucaites V.L., Nelson D.L., Nichols D.E. Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N, N-dimethyltryptamine. J. Med. Chem. 1999, 42(6):1106-1111.
49. Yous S., Andrieux J., Howell H.E., Morgan P.J., Renard P., Pfeiffer B., Lesieur D., Guardiola-Lemaitre B. Novel naphthalenic ligands with high affinity for the melatonin receptor. J. Med. Chem. 1992, 35(8):1484-1486.
50. Depreux P., Lesieur D., Mansour H.A., Morgan P., Howell H.E., Renard P., Caignard D.H., Pfeiffer B., Delagrange P., Guardiola B., et al. Synthesis and structure-activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands. J. Med. Chem. 1994, 37(20):3231-3239.
51. Blaskó G., Major E., Blaskó G., Rózsa I., Szántay C. Pyrimido[1,6-a]pyrido[3,4-b] indoles as new platelet inhibiting agents. Eur. J. Med. Chem. 1986, 21:91-95.
52. Kardos J., Blaskó G., Simonyi M., Szántay C. Octahydroindolo[2,3-a]quinolizin-2-one, a novel structure for γ-aminobutyric acid (GABA) uptake inhibition. Eur. J. Med. Chem. 1985, 21:151-154.
53. Salituro F.G., Harrison B.L., Baron B.M., Nyce P.L., Stewart K.T., Kehne J.H., White H.S., McDonald I. 3-(2-Carboxyindol-3-yl)propionic acid-based antagonists of the N-methyl-d-aspartic receptor associated glycine binding site. J. Med. Chem. 1992, 35:1791-1799.
54. Calvino R., Stilo A.Di., Fruttero R., Gasco A.M., Sorba G., Gasco A. Pharmacochemistry of the furoxan ring: recent developments. Il Farmaco 1993, 48:321-334.
55. Lipinski C.A., Aldinger C.E., Beyer T.A., Bordner J., Burdi D.F., Bussolotti D.L., Inskeep P.B., Siegel T.W. Hydantoin isosteres. In vivo active spiro hydroxy acetic aldose reductase inhibitors. J. Med. Chem. 1992, 35:2169-2177.
56. Lober S., Hubner H., Gmeiner P. Fused azaindole derivatives: molecular design, synthesis and in vitro pharmacology leading to the preferential dopamine D3 receptor agonist FAUC 725. Bioorg. Med. Chem. Lett. 2002, 12(17):2377-2380.
57. Krogsgaard-Larsen P., Hjeds H., Falch E., Jørgensen F.S., Nielsen L. Recent advances in GABA agonists, antagonists and uptake inhibitors: structure-activity relationships and therapeutic potential. Advances in Drug Research 1988, Vol. 17:381-456. Academic Press, London. B. Testa (Ed.).
58. Almquist R.G., Chao W.R., Jennings-White C. Synthesis and biological activity of carboxylic acid replacement analogues of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-l-proline. J. Med. Chem. 1985, 28:1067-1071.
59. Massa S., Mai A., Sbardella G., Esposito M., Ragno R., Loidl P., Brosch G. 3-(4-Aroyl-1H-pyrrol-2-yl)-N-hydroxy-2-propenamides, a new class of synthetic histone deacetylase inhibitors. J. Med. Chem. 2001, 44(13):2069-2072.
60. Lu Q., Yang Y.T., Chen C.S., Davis M., Byrd J.C., Etherton M.R., Umar A., Chen C.S. Zn2+-chelating motif-tethered short-chain fatty acids as a novel class of histone deacetylase inhibitors. J. Med. Chem. 2004, 47(2):467-474.
61. Remiszewski S.W., Sambucetti L.C., Bair K.W., Bontempo J., Cesarz D., Chandramouli N., Chen R., Cheung M., Cornell-Kennon S., Dean K., Diamantidis G., France D., Green M.A., Howell K.L., Kashi R., Kwon P., Lassota P., Martin M.S., Mou Y., Perez L.B., Sharma S., Smith T., Sorensen E., Taplin F., Trogani N., Versace R., Walker H., Weltchek-Engler S., Wood A., Wu A., Atadja P. N-hydroxy-3-phenyl-2-propenamides as novel inhibitors of human histone deacetylase with in vivo antitumor activity: discovery of (2E)-N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]meth yl]phenyl]-2-propenamide (NVP-LAQ824). J. Med. Chem. 2003, 46(21):4609-4624.
62. Plumb J.A., Finn P.W., Williams R.J., Bandara M.J., Romero M.R., Watkins C.J., La Thangue N.B., Brown R. Pharmacodynamic response and inhibition of growth of human tumor xenografts by the novel histone deacetylase inhibitor PXD101. Mol. Cancer Ther. 2003, 2(8):721-728.
63. Kelly W.K., O'Connor O.A., Krug L.M., Chiao J.H., Heaney M., Curley T., MacGregore-Cortelli B., Tong W., Secrist J.P., Schwartz L., Richardson S., Chu E., Olgac S., Marks P.A., Scher H., Richon V.M. Phase I study of an oral histone deacetylase inhibitor, suberoylanilide hydroxamic acid, in patients with advanced cancer. J. Clin. Oncol. 2005, 2(17):3923-3931.
64. Buggy J.J., Cao Z.A., Bass K.E., Verner E., Balasubramanian S., Liu L., Schultz B.E., Young P.R., Dalrymple S.A. CRA-024781: a novel synthetic inhibitor of histone deacetylase enzymes with antitumor activity in vitro and in vivo. Mol. Cancer Ther. 2006, 5(5):1309-1317.
65. Hanessian S., Moitessier N., Gauchet C., Viau M. N-aryl sulfonyl homocysteine hydroxamate inhibitors of matrix metalloproteinases: further probing of the S(1), S(1)', and S(2)' pockets. J. Med. Chem. 2001, 44(19):3066-3073.
66. Aranapakam V., Davis J.M., Grosu G.T., Baker J., Ellingboe J., Zask A., Levin J.I., Sandanayaka V.P., Du M., Skotnicki J.S., DiJoseph J.F., Sung A., Sharr M.A., Killar L.M., Walter T., Jin G., Cowling R., Tillett J., Zhao W., McDevitt J., Xu Z.B. Synthesis and structure-activity relationship of N-substituted 4-arylsulfonylpiperidine-4-hydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis. J. Med. Chem. 2003, 46(12):2376-2396.
67. Aranapakam V., Grosu G.T., Davis J.M., Hu B., Ellingboe J., Baker J.L., Skotnicki J.S., Zask A., DiJoseph J.F., Sung A., Sharr M.A., Killar L.M., Walter T., Jin G., Cowling R. Synthesis and structure-activity relationship of alpha-sulfonylhydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis. J. Med. Chem. 2003, 46(12):2361-2375.
68. Noe M.C., Natarajan V., Snow S.L., Mitchell P.G., Lopresti-Morrow L., Reeves L.M., Yocum S.A., Carty T.J., Barberia J.A., Sweeney F.J., Liras J.L., Vaughn M., Hardink J.R., Hawkins J.M., Tokar C. Discovery of 3,3-dimethyl-5-hydroxypipecolic hydroxamate-based inhibitors of aggrecanase and MMP-13. Bioorg. Med. Chem. Lett. 2005, 15(11):2808-2811.
69. Duan J.J., Chen L., Wasserman Z.R., Lu Z., Liu R.Q., Covington M.B., Qian M., Hardman K.D., Magolda R.L., Newton R.C., Christ D.D., Wexler R.R., Decicco C.P. Discovery of gamma-lactam hydroxamic acids as selective inhibitors of tumor necrosis factor alpha converting enzyme: design, synthesis, and structure-activity relationships. J. Med. Chem. 2002, 45(23):4954-4957.
70. 2- und NCN- Gruppen. Z. Anorg. Chem. 1970, 379:183-192.
71. Kwon C.-H., Nagasawa H.T., DeMaster E.G., Shirota F.N. Acyl, N-protected α-aminoacyl, and peptidyl derivatives as prodrug forms of the alcohol deterrent agent cyanamide. J. Med. Chem. 1986, 29:1922-1929.
72. Drummond J.T., Johnson G. Convenient procedure for the preparation of alkyl end aryl substituted N-(aminoalkylacyl)sulfonamides. Tetrahedron Let 1988, 29:1653-1656.
73. Albright J.D., DeVries V.G., Du M.D., Largis E.E., Miner T.G., Reich M.F., Shepherd R.G. Potential antiatherosclerotic agents. 3. Substituted benzoic and non benzoic analogues of cetabon. J. Med. Chem. 1983, 26:1393-1411.
74. Uehling D.E., Donaldson K.H., Deaton D.N., Hyman C.E., Sugg E.E., Barrett D.G., Hughes R.G., Reitter B., Adkison K.K., Lancaster M.E., Lee F., Hart R., Paulik M.A., Sherman B.W., True T., Cowan C. Synthesis and evaluation of potent and selective beta(3) adrenergic receptor agonists containing acylsulfonamide, sulfonylsulfonamide, and sulfonylurea carboxylic acid isosteres. J. Med. Chem. 2002, 45(3):567-583.
75. Johansson A., Poliakov A., Akerblom E., Wiklund K., Lindeberg G., Winiwarter S., Danielson U.H., Samuelsson B., Hallberg A. Acyl sulfonamides as potent protease inhibitors of the hepatitis C virus full-length NS3 (protease-helicase/NTPase): a comparative study of different C-terminals. Bioorg. Med. Chem. 2003, 11(12):2551-2568.
76. Noe M.C., Natarajan V., Snow S.L., Wolf-Gouveia L.A., Mitchell P.G., Lopresti-Morrow L., Reeves L.M., Yocum S.A., Otterness I., Bliven M.A., Carty T.J., Barberia J.T., Sweeney F.J., Liras J.L., Vaughn M. Discovery of 3-OH-3-methylpipecolic hydroxamates: potent orally active inhibitors of aggrecanase and MMP-13. Bioorg. Med. Chem. Lett. 2005, 15(14):3385-3388.
77. Buu-Hoï N.P., Lambelin G., Lepoivre C., Gillet C., Gautier M., Thiriaux J. Un nouvel agent antiinflammatoire de structure non stéroïdique: l'acide p-butoxyphénylacéthydroxamique. C. R. Acad. Sci.(Paris). 1965, 261:2259-2262.
78. Orzalesi, G., Selleri, R., Pharmaceutical 2-(4-isobutylphenyl) propionohydroxamic acid. Ger. Offen. 2,400,531 (24 Jul. 1974, to Societa Italo-Britannica L. Manetti & H.Roberts e C.). 1974, C.A. 1974; 81; 120272i.
79. De Martiis F., Franzone J.S., Tamietto T. Sintesi e Proprieta Antiflogistiche di Alcuni Acidici Indolil-Acetoidrossammici. Bol. Chim. Farm. 1975, 114:309-318.
80. Orzalesi G., Mari F., Bertol E., Selleri R., Pisaturo G. Anti-inflammatory agents: determination of ibuproxam and its metabolite in humans. Arzneim.-Forsch. 1980, 30:1607-1609.
81. Demay F., De Sy J. A new non-steroidal anti-inflammatory drug (NSAID) in current rheumatologic practice (oxamethacin). Curr. Ther. Res. 1982, 31:113-118.
82. Vergin H., Ferber H., Brunner F., Kukovetz W.R. Pharmakokinetik und Biotransformation von Oxametacin bei gesunden Probanden. Arzneim.-Forsch. 1981, 31:513-518.
83. Allegretti M., Bertini R., Cesta M.C., Bizzarri C., Di Bitondo R., Di Cioccio V., Galliera E., Berdini V., Topai A., Zampella G., Russo V., Di Bello N., Nano G., Nicolini L., Locati M., Fantucci P., Florio S., Colotta F. 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. J. Med. Chem. 2005, 48(13):4312-4331.
84. Wan Y., Wallinder C., Johansson B., Holm M., Mahalingam A.K., Wu X., Botros M., Karlen A., Pettersson A., Nyberg F., Fandriks L., Hallberg A., Alterman M. First reported nonpeptide AT1 receptor agonist (L-162,313) acts as an AT2 receptor agonist in vivo. J. Med. Chem. 2004, 47(6):1536-1546.
85. Lobb K.L., Hipskind P.A., Aikins J.A., Alvarez E., Cheung Y.Y., Considine E.L., De Dios A., Durst G.L., Ferritto R., Grossman C.S., Giera D.D., Hollister B.A., Huang Z., Iversen P.W., Law K.L., Li T., Lin H.S., Lopez B., Lopez J.E., Cabrejas L.M., McCann D.J., Molero V., Reilly J.E., Richett M.E., Shih C., Teicher B., Wikel J.H., White W.T., Mader M.M. Acyl sulfonamide anti-proliferatives: benzene substituent structure-activity relationships for a novel class of antitumor agents. J. Med. Chem. 2004, 47(22):5367-5380.
86. Mader M.M., Shih C., Considine E., Dios A.D., Grossman C.S., Hipskind P.A., Lin H.S., Lobb K.L., Lopez B., Lopez J.E., Cabrejas L.M., Richett M.E., White W.T., Cheung Y.Y., Huang Z., Reilly J.E., Dinn S.R. Acyl sulfonamide anti-proliferatives. Part 2: activity of heterocyclic sulfonamide derivatives. Bioorg. Med. Chem. Lett. 2005, 15(3):617-620.
87. Hattori K., Tanaka A., Fujii N., Takasugi H., Tenda Y., Tomita M., Nakazato S., Nakano K., Kato Y., Kono Y., Murai H., Sakane K. Discovery of diphenyloxazole and Ndelta-Z-ornithine derivatives as highly potent and selective human prostaglandin EP(4) receptor antagonists. J. Med. Chem. 2005, 48(9):3103-3106.
88. Bovy P.R., Reitz D.B., Collins J.T., Chamberlain T.S., Olins G.M., Corpus V.M., Mc Mahon E.G., Palomo M.A., Koepke J.P., McGraw D.E., Gaw G.J. Nonpeptide angiotensin II antagonists: N-phenyl-1-H-pyrrole derivatives are angiotensin II receptor antagonists. J. Med. Chem. 1993, 36:101-110.
89. Marshall W.S., Goodson T., Cullinan G.J., Swanson-Bean D., Haisch K.D., Rinkema L.E., Fleisch J.H. Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives. J. Med. Chem. 1987, 30:682-689.
90. Krogsgaard-Larsen P. Comprehensive Medicinal Chemistry 1990, Vol. 3:493-537. Pergamon Press, Oxford. C. Hansch, P.G. Sammes, J.B. Taylor, J.C. Emmet (Eds.).
91. Lunn, W. H. W., Schoepp, D. D., Lodge, D., True, R. A., Millar, J. D. Poster N° P-041.A. LY262466, DL-2-amino-3-(4-hydroxy-1,2,5-thiazol-3-yl) propanoic acid hydrochloride, a novel and selective agonist at the AMPA excitatory amino acid receptor, XIIth International Symposium on Medicinal Chemistry, Basel, Switzerland, September 13-17, 1992, pp. 113-117.
92. Atkinson J.G., Girard Y., Rokach J., Rooney C.S., McFarlane C.S., Rackham A., Share N.N. Kojic amine-A novel γ-aminobutyric acid analogue. J. Med. Chem. 1979, 22:90-106.
93. Hulin B., McCarthy P.A., Gibbs E.M. The glitazone family of antidiabetic agents. Curr. Pharm. Des. 1996, 2:85-102.
94. Henke B.R. Peroxisome proliferator-activated receptor alpha/gamma dual agonists for the treatment of type 2 diabetes. J. Med. Chem. 2004, 47(17):4118-4127.
95. Gezginci M.H., Martin A.R., Franzblau S.G. Antimycobacterial activity of substituted isosteres of pyridine- and pyrazinecarboxylic acids. 2. J. Med. Chem. 2001, 44(10):1560-1563.
96. Nicolaou I., Zika C., Demopoulos V.J. [1-(3,5-Difluoro-4-hydroxyphenyl)-1H-pyrrol-3-yl]phenylmethanone as a bioisostere of a carboxylic acid aldose reductase inhibitor. J. Med. Chem. 2004, 47(10):2706-2709.
97. Qiu J., Stevenson S.H., O'Beirne M.J., Silverman R.B. 2,6-Difluorophenol as a bioisostere of a carboxylic acid: bioisosteric analogues of gamma-aminobutyric acid. J. Med. Chem. 1999, 42(2):329-332.
98. Liljebris C., Larsen S.D., Ogg D., Palazuk B.J., Bleasdale J.E. Investigation of potential bioisosteric replacements for the carboxyl groups of peptidomimetic inhibitors of protein tyrosine phosphatase 1B: identification of a tetrazole-containing inhibitor with cellular activity. J. Med. Chem. 2002, 45(9):1785-1798.
99. Momose Y., Maekawa T., Odaka H., Ikeda H., Sohda T. Novel 5-substituted-1H-tetrazole derivatives as potent glucose and lipid lowering agents. Chem. Pharm. Bull. (Tokyo) 2002, 50(1):100-111.
100. Biot C., Bauer H., Schirmer R.H., Davioud-Charvet E. 5-Substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials. J. Med. Chem. 2004, 47(24):5972-5983.
101. Kimura T., Shuto D., Hamada Y., Igawa N., Kasai S., Liu P., Hidaka K., Hamada T., Hayashi Y., Kiso Y. Design and synthesis of highly active Alzheimer's beta-secretase (BACE1) inhibitors, KMI-420 and KMI-429, with enhanced chemical stability. Bioorg. Med. Chem. Lett. 2005, 15(1):211-215.
102. Roppe J., Smith N.D., Huang D., Tehrani L., Wang B., Anderson J., Brodkin J., Chung J., Jiang X., King C., Munoz B., Varney M.A., Prasit P., Cosford N.D. Discovery of novel heteroarylazoles that are metabotropic glutamate subtype 5 receptor antagonists with anxiolytic activity. J. Med. Chem. 2004, 47(19):4645-4648.
103. Kozikowski A.P., Zhang J., Nan F., Petukhov P.A., Grajkowska E., Wroblewski J.T., Yamamoto T., Bzdega T., Wroblewska B., Neale J.H. Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: efficacy as analgesic agents. J. Med. Chem. 2004, 47(7):1729-1738.
104. Valgeirsson J., Nielsen E.O., Peters D., Mathiesen C., Kristensen A.S., Madsen U. Bioisosteric modifications of 2-arylureidobenzoic acids: selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5. J. Med. Chem. 2004, 47(27):6948-6957.
105. Kraus J.L. Isosterism and molecular modification in drug design: tetrazole analogue of GABA: effects on enzymes of the gamma-aminobutyrate system. Pharmacol. Res. Commun. 1983, 15:183-189.
106. Hallinan E.A., Tsymbalov S., Dorn C.R., Pitzele B.S., Hansen D.W., Moore W.M., Jerome G.M., Connor J.R., Branson L.F., Widomski D.L., Zhang Y., Currie M.G., Manning P.T. Synthesis and biological characterization of L-N(6)-(1-iminoethyl)lysine 5-tetrazole-amide, a prodrug of a selective iNOS inhibitor. J. Med. Chem. 2002, 45(8):1686-1689.
107. Schlewer G., Wermuth C.G., Chambon J.-P. Analogues tétrazoliques d'agents GABA-mimétiques. Eur. J. Med. Chem. 1984, 19:181-186.
108. Krogsgaard-Larsen P., Ferkany J.W., Nielsen E.O., Madsen U., Ebert B., Johansen J.S., Diemer S.H., Bruhn T., Beattie D.T., Curtis D.R. Novel class of amino acid antagonists at non-N-methyl-d-aspartic acid excitatory amino acid receptors. Synthesis, in vitro and in vivo pharmacology, and neuroprotection. J. Med. Chem. 1991, 34:123-130.
109. Krogsgaard-Larsen P., Rodolskov-Christiansen T. GABA agonists. Synthesis and structure-activity studies on analogues of isoguvacine and THIP. Eur. J. Med. Chem. 1979, 14:157-164.
110. Kraus J.L. Isosterism and molecular modification in drug design: new n-dipropylacetate analogs as inhibitors of succinic semi aldehyde dehydrogenase. Pharmacol. Res. Commun. 1983, 15:119-129.
111. Lichtenthaler F.W., Heidel P. Intermediates in the formation of γ-pyrones from hexose derivatives: a simple synthesis of kojic acid and hydroxymaltol. Angew. Chem. Int. Ed. 1969, 8:978-979.
112. B antagonists: novel CNS-active compounds. Perspectives in Medicinal Chemistry 1993, 259-272. VHC, Weinheim. B. Testa, E. Kyburz, W. Fuhrer, R. Giger (Eds.).
113. Rosowski A., Forsch R.A., Freisheim J.H., Moran R.G., Wick M. Methotrexate analogues. 19. Replacement of the glutamate side chain in classical antifolates by l-homocysteic acid and l-cysteic acid: effect on enzyme inhibition and antitumor activity. J. Med. Chem. 1984, 27:600-604.
114. Watkins J.C., Krogsgaard-Larsen P., Honoré T. Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. Trends Pharm. Sci. 1990, 11:25-33.
115. Drysdale M.J., Pritchard M.C., Horwell D.C. Rationally designed "dipeptoid" analogues of CCK. Acid mimics of the potent and selective non peptide CCK-B receptor antagonist CI-988. J. Med. Chem. 1992, 35:2573-2581.
116. Franz R.D. Comparisons of pKa and log P values of some carboxylic and phosphonic acids: synthesis and measurement. AAPS PharmSci. 2001, 3(2):E10.
117. Kinney W.A., Lee N.E., Garrison D.T., Podlesny E.J., Simmonds J.T., Bramlet D., Notvest R.R., Kowal D.M., Tasse R.P. Bioisosteric replacement of the α-amino carboxylic functionality in 2-amino-5-phosphonopentanoic acid yields unique 3,4-diamino-3-cyclobutene-1,2-dione containing NMDA antagonists. J. Med. Chem. 1992, 35:4720-4726.
118. Gao Y., Luo J., Yao Z.-J., Guo R., Zou H., Kelley J., Voigt J.H., Yang D., Burke T.R. Inhibition of Grb2 SH2 domain binding by non-phosphate-containing ligands. 2. 4-(2-Malonyl)phenylalanine as a potent phosphotyrosyl mimetic. J. Med. Chem. 2000, 43:911-920.
119. 1 receptor. J. Med. Chem. 1992, 35:15-27.
120. Thompkins L., Lee K.H. Comparison of analgesic effects of isosteric variations of salicylic acid and aspirin (acetylsalicylic acid). J. Pharm. Sci. 1975, 64:760-763.
121. Roth G.J., Stanford N., Majerus P.W. Acetylation of prostaglandine synthase by aspirin. Proc. Nat. Acad. Sci. USA 1975, 72:3073-3076.
122. Bundgaard H. Design of Prodrugs 1985, Elsevier, Amsterdam, p. 55-61.
123. Sauerberg P., Chen J., WoldeMussie E., Rapoport H. Cyclic carbamate analogues of pilocarpine. J. Med. Chem. 1989, 32:1322-1326.
124. Sauerberg P., Kindtler J.W., Nielsen L., Sheardown M.J., Honoré T. Muscarinic cholinergic agonists and antagonists of the 3-(3-alkyl-1,2,4-oxadiazol-5-yl)1,2,5,6-tetrahydropyridine type synthesis and structure-activity relationships. J. Med. Chem. 1991, 34:687-692.
125. 1selective muscarinic agonists. Synthesis and structure-activity relationships of 3-(1,2,5-thiadiazolyl)-1,2,5,6-tetrahydro-1-methylpyridines. J. Med. Chem. 1992, 35:2263-2274.
126. Sauerberg P., Larsen J.J., Falch E., Krogsgaard-Larsen P. A novel class of conformationally restricted heterocyclic muscarinic agonists. J. Med. Chem. 1986, 29(6):1004-1009.
127. Saunders J., Cassidy M., Freedman S.B., Harley E.A., Iversen L.L., Kneen C., MacLeod A.M., Merchant K., Snow R.J., Baker R. Novel quinuclidine-based ligands for the muscarinic cholinergic receptor. J. Med. Chem. 1990, 33:1128-1138.
128. Street L.J., Baker R., Book T., Reeve A.J., Saunders J., Willson T., Marwood R.S., Patel S., Freedman S.B. Synthesis and muscarinic activity of quinuclidinyl- and (1-azanorbornyl)pyrazine derivatives. J. Med. Chem. 1992, 35:295-305.
129. Wadsworth H.J., Jenkins S.M., Orlek B.S., Cassidy F., Clark M.S.G., Brown F., Riley G.J., Graves D., Hawkins J., Naylor C. Synthesis and muscarinic activities of quinuclidin-3-yltriazole and -tetrazole derivatives. J. Med. Chem. 1992, 35:1280-1290.
130. Jenkins S.M., Wadsworth H.J., Bromidge S., Orlek B.S., Wyman P.A., Riley G.J., Hawkins J. Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands. J. Med. Chem. 1992, 35(13):2392-2406.
131. Bromidge S.M., Brown F., Cassidy F., Clark M.S., Dabbs S., Hadley M.S., Hawkins J., Loudon J.M., Naylor C.B., Orlek B.S., Riley G.J. Design of [R-(Z)]-(+)-alpha-(methoxyimino)-1-azabicyclo[2.2.2]octane-3-acetonitri le (SB 202026), a functionally selective azabicyclic muscarinic M1 agonist incorporating the N-methoxy imidoyl nitrile group as a novel ester bioisostere. J. Med. Chem. 1997, 40(26):4265-4280.
132. Toja E., Bonetti C., Butti A., Hunt P., Fortin M., Barzaghi F., Formento M.L., Maggioni A., Nencioni A., Galliani G. 1-Alkyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyl-oximes: a new class of potent orally available active muscarinic agaonists related to arecoline. Eur. J. Med. Chem. 1991, 22:853-868.
133. Carroll F.I. 2002 Medicinal Chemistry Division Award address: monoamine transporters and opioid receptors. Targets for addiction therapy. J. Med. Chem. 2003, 46(10):1775-1794.
134. Petukhov P.A., Zhang M., Johnson K.J., Tella S.R., Kozikowski A.P. Sar studies of piperidine-based analogues of cocaine. Part 3: oxadiazoles,. Bioorg. Med. Chem. Lett. 2001, 11(16):2079-2083.
135. Street L.J., Baker R., Castro J.L., Chambers M.S., Guiblin A.R., Hobbs S.C., Matassa V.G., Reeve A.J., Beer M.S., Middlemiss D.N., et al. Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors. J. Med. Chem. 1993, 36(11):1529-1538.
136. Kuduk S.D., Ng C., Feng D.M., Wai J.M., Chang R.S., Harrell C.M., Murphy K.L., Ransom R.W., Reiss D., Ivarsson M., Mason G., Boyce S., Tang C., Prueksaritanont T., Freidinger R.M., Pettibone D.J., Bock M.G. 2,3-Diaminopyridine bradykinin B1 receptor antagonists. J. Med. Chem. 2004, 47(26):6439-6442.
137. Borzilleri R.M., Zheng X., Qian L., Ellis C., Cai Z.W., Wautlet B.S., Mortillo S., Jeyaseelan R., Kukral D.W., Fura A., Kamath A., Vyas V., Tokarski J.S., Barrish J.C., Hunt J.T., Lombardo L.J., Fargnoli J., Bhide R.S. Design, synthesis, and evaluation of orally active 4-(2,4-difluoro-5-(methoxycarbamoyl)phenylamino)pyrrolo[2,1-f][1,2,4]tri az ines as dual vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 inhibitors. J. Med. Chem. 2005, 48(12):3991-4008.
138. Sakamoto T., Cullen M.D., Hartman T.L., Watson K.M., Buckheit R.W., Pannecouque C., De Clercq E., Cushman M. Synthesis and anti-HIV activity of new metabolically stable alkenyldiarylmethane non-nucleoside reverse transcriptase inhibitors incorporating N-methoxy imidoyl halide and 1,2,4-oxadiazole systems. J. Med. Chem. 2007, 50(14):3314-3321.
139. Deng B.L., Hartman T.L., Buckheit R.W., Pannecouque C., De Clercq E., Cushman M. Replacement of the metabolically labile methyl esters in the alkenyldiarylmethane series of non-nucleoside reverse transcriptase inhibitors with isoxazolone, isoxazole, oxazolone, or cyano substituents. J. Med. Chem. 2006, 49(17):5316-5323.
140. Watson K.G., Brown R.N., Cameron R., Chalmers D.K., Hamilton S., Jin B., Krippner G.Y., Luttick A., McConnell D.B., Reece P.A., Ryan J., Stanislawski P.C., Tucker S.P., Wu W.Y., Barnard D.L., Sidwell R.W. An orally bioavailable oxime ether capsid binder with potent activity against human rhinovirus. J. Med. Chem. 2003, 46(15):3181-3184.
141. Kozikowski A.P., Roberti M., Xiang L., Bergmann J.S., Callahan P.M., Cunningham K.A., Johnson K.M. Structure-activity relationship studies of cocaine: replacement of the C-2 ester group by vinyl argues against H-bonding and provides an esterase-resistant, high-affinity cocaine analogue. J. Med. Chem. 1992, 35:4764-4766.
142. Lipinski C.A. Bioisosterism in drug design. Annual Report in Medicinal Chemistry 1986, Vol. 21:283-291. Academic Press, San Diego. D.M. Bailey (Ed.).
143. Wermuth C.G. Aminopyridazines - an alternate route to potent muscarinic agonists with no cholinergic syndrome. Il Farmaco 1993, 48:253-274.
144. 2-adrenoreceptor antagonist. J. Med. Chem. 1985, 28:1756-1759.
145. Spatola A.F. Peptide backbone modifications: structure-activity analysis of peptides containing amide bond surrogates. Chemistry and Biochemistry of Amino Acids, Peptides and Proteins 1983, Vol. 7:267-357. Marcel Dekker, New York. B. Weinstein (Ed.).
146. Fauchère J.-L. Elements for the rational design of peptide drugs. Advances in Drug Research 1986, Vol. 15:29-69. Academic Press, London. B. Testa (Ed.).
147. Fournier J.-P., Moreau R.C., Narcisse G., Choay P. Synthèse et propriétés pharmacologiques de sulfonylurées isostères du glibenclamide. Eur. J. Med. Chem. 1982, 17:81-84.
148. Smith A.B., Holcomb R.C., Guzman M.C., Keenan T.P., Sprengeler P.A., Hirschmann R. An Effective Synthesis of Scalemic 3,5,5-Trisubstituted Pyrrolin-4-ones. Tetrahedron Lett. 1993, 34:63-66.
149. Smith A.B., Keenan T.P., Holcomb R.C., Sprengeler P.A., Guzman M.C., Wood J.L., Caroll P.J., Hirschmann R. Design, synthesis, and crystal structure of a pyrrolinone-based peptidomimetic possessing the conformation of a β-strand: potential application to the design of novel inhibitors of proteolytic enzymes. J. Amer. Chem. Soc. 1992, 114:10672-10674.
150. Allmendinger T., Felder E., Hungerbuehler E. Fluoroolefin dipeptide isosteres. Selective Fluorination in Organic and Bioorganic Chemistry 1991, 186-195. American Chemical Society, Washington, Vol. ACS Symp. 456. J.T. Weldi (Ed.).
151. Chandrakumar N.S., Yonan P.K., Stapelfeld A., Svage M., Rorbacher E., Contreras P.C., Hammond D. Preparation and opioid activity of analogues of the analgesic dipeptide 2,6-dimethyl-l-tyrosyl-N-(3-phenylpropyl)-d-alanylamide. J. Med. Chem. 1992, 35:223-233.
152. Vu C.B., Corpuz E.G., Merry T.J., Pradeepan S.G., Bartlett C., Bohacek R.S., Botfield M.C., Eyermann C.J., Lynch B.A., MacNeil I.A., Ram M.K., van Schravendijk M.R., Violette S., Sawyer T.K. Discovery of potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70. J. Med. Chem. 1992, 42(20):4088-4098.
153. 3 receptor antagonists. Bioorg. Med. Chem. Lett. 1996, 6:833-838.
154. Swain C.J., Baker R., Kneen C., Moseley J., Saunders J., Seward E.M., Stevenson G., Beer M., Stanton J., Watling K. Novel 5-HT3 antagonists. Indole oxadiazoles. J. Med. Chem. 1991, 34(1):140-151.
155. Biftu T., Feng D.D., Liang G.B., Kuo H., Qian X., Naylor E.M., Colandrea V.J., Candelore M.R., Cascieri M.A., Colwell L.F., Forrest M.J., Hom G.J., MacIntyre D.E., Stearns R.A., Strader C.D., Wyvratt M.J., Fisher M.H., Weber A.E. Synthesis and SAR of benzyl and phenoxymethylene oxadiazole benzenesulfonamides as selective beta3 adrenergic receptor agonist antiobesity agents. Bioorg. Med. Chem. Lett. 2000, 10(13):1431-1434.
156. Feng D.D., Biftu T., Candelore M.R., Cascieri M.A., Colwell L.F., Deng L., Feeney W.P., Forrest M.J., Hom G.J., MacIntyre D.E., Miller R.R., Stearns R.A., Strader C.D., Tota L., Wyvratt M.J., Fisher M.H., Weber A.E. Discovery of an orally bioavailable alkyl oxadiazole beta3 adrenergic receptor agonist. Bioorg. Med. Chem. Lett. 2000, 10(13):1427-1429.
157. Naylor E.M., Colandrea V.J., Candelore M.R., Cascieri M.A., Colwell L.F., Deng L., Feeney W.P., Forrest M.J., Hom G.J., MacIntyre D.E., Strader C.D., Tota L., Wang P.R., Wyvratt M.J., Fisher M.H., Weber A.E. 3-Pyridylethanolamines: potent and selective human beta 3 adrenergic receptor agonists. Bioorg. Med. Chem. Lett. 1998, 8(21):3087-3092.
158. Naylor E.M., Parmee E.R., Colandrea V.J., Perkins L., Brockunier L., Candelore M.R., Cascieri M.A., Colwell L.F., Deng L., Feeney W.P., Forrest M.J., Hom G.J., MacIntyre D.E., Strader C.D., Tota L., Wang P.R., Wyvratt M.J., Fisher M.H., Weber A.E. Human beta3 adrenergic receptor agonists containing imidazolidinone and imidazolone benzenesulfonamides. Bioorg. Med. Chem. Lett. 1999, 9(5):755-758.
159. Parmee E.R., Naylor E.M., Perkins L., Colandrea V.J., Ok H.O., Candelore M.R., Cascieri M.A., Deng L., Feeney W.P., Forrest M.J., Hom G.J., MacIntyre D.E., Miller R.R., Stearns R.A., Strader C.D., Tota L., Wyvratt M.J., Fisher M.H., Weber A.E. Human beta3 adrenergic receptor agonists containing cyclic ureidobenzenesulfonamides. Bioorg. Med. Chem. Lett. 1999, 9(5):749-754.
160. Tully W.R., Gardner C.R., Gillespie R.J., Westwood R. 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors. J. Med. Chem. 1991, 34(7):2060-2067.
161. Orlek B.S., Blaney F.E., Brown F., Clark M.S., Hadley M.S., Hatcher J., Riley G.J., Rosenberg H.E., Wadsworth H.J., Wyman P. Comparison of azabicyclic esters and oxadiazoles as ligands for the muscarinic receptor. J. Med. Chem. 1991, 34(9):2726-2735.
162. Ladduwahetty T., Baker R., Cascieri M.A., Chambers M.S., Haworth K., Keown L.E., MacIntyre D.E., Metzger J.M., Owen S., Rycroft W., Sadowski S., Seward E.M., Shepheard S.L., Swain C.J., Tattersall F.D., Watt A.P., Williamson D.W., Hargreaves R.J. N-heteroaryl-2-phenyl-3-(benzyloxy)piperidines: a novel class of potent orally active human NK1 antagonists. J. Med. Chem. 1996, 39(15):2907-2914.
163. Borg S., Vollinga R.C., Labarre M., Payza K., Terenius L., Luthman K. Design, synthesis, and evaluation of Phe-Gly mimetics: heterocyclic building blocks for pseudopeptides. J. Med. Chem. 1999, 42(21):4331-4342.
164. Elzein E., Ibrahim P., Koltun D.O., Rehder K., Shenk K.D., Marquart T.A., Jiang B., Li X., Natero R., Li Y., Nguyen M., Kerwar S., Chu N., Soohoo D., Hao J., Maydanik V.Y., Lustig D.A., Zeng D., Leung K., Zablocki J.A. CVT-4325: a potent fatty acid oxidation inhibitor with favorable oral bioavailability. Bioorg. Med. Chem. Lett. 2004, 14(24):6017-6021.
165. Koltun D.O., Marquart T.A., Shenk K.D., Elzein E., Li Y., Nguyen M., Kerwar S., Zeng D., Chu N., Soohoo D., Hao J., Maydanik V.Y., Lustig D.A., Ng K.J., Fraser H., Zablocki J.A. New fatty acid oxidation inhibitors with increased potency lacking adverse metabolic and electrophysiological properties. Bioorg. Med. Chem. Lett. 2004, 14(2):549-552.
166. Einsiedel J., Hubner H., Gmeiner P. Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179). Bioorg. Med. Chem. Lett. 2001, 11(18):2533-2536.
167. Einsiedel J., Hubner H., Gmeiner P. Cyclic amidines as benzamide bioisosteres: EPC synthesis and SAR studies leading to the selective dopamine D4 receptor agonist FAUC 312. Bioorg. Med. Chem. Lett. 2003, 13(5):851-854.
168. Einsiedel J., Thomas C., Hubner H., Gmeiner P. Phenyloxazoles and phenylthiazoles as benzamide bioisosteres: synthesis and dopamine receptor binding profiles. Bioorg. Med. Chem. Lett. 2000, 10(17):2041-2044.
169. Thurkauf A., Yuan J., Chen X., He X.S., Wasley J.W., Hutchison A., Woodruff K.H., Meade R., Hoffman D.C., Donovan H., Jones-Hertzog D.K. 2-Phenyl-4(5)-[[4-(pyrimidin-2-yl)piperazin-1-yl]methyl]imidazole. A highly selective antagonist at cloned human D4 receptors. J. Med. Chem. 1997, 40(1):1-3.
170. Fletcher S.R., McIver E., Lewis S., Burkamp F., Leech C., Mason G., Boyce S., Morrison D., Richards G., Sutton K., Jones A.B. The search for novel TRPV1-antagonists: from carboxamides to benzimidazoles and indazolones. Bioorg. Med. Chem. Lett. 2006, 16(11):2872-2876.
171. Wu W.L., Burnett D.A., Caplen M.A., Domalski M.S., Bennett C., Greenlee W.J., Hawes B.E., O'Neill K., Weig B., Weston D., Spar B., Kowalski T. Design and synthesis of orally efficacious benzimidazoles as melanin-concentrating hormone receptor 1 antagonists. Bioorg. Med. Chem. Lett. 2006, 16(14):3674-3678.
172. Wu W.L., Burnett D.A., Spring R., Qiang L., Sasikumar T.K., Domalski M.S., Greenlee W.J., O'Neill K., Hawes B.E. Synthesis and structure-activity relationships of piperidine-based melanin-concentrating hormone receptor 1 antagonists. Bioorg. Med. Chem. Lett. 2006, 16(14):3668-3673.
173. Lanter J.C., Fiordeliso J.J., Allan G.F., Musto A., Hahn do W., Sui Z. A bioisosteric approach to the discovery of indole carbinol androgen receptor ligands. Bioorg. Med. Chem. Lett. 2006, 16(21):5646-5649.
174. Wouters J., Michaux C., Durant F., Dogne J.M., Delarge J., Masereel B. Isosterism among analogues of torasemide: conformational, electronic and lipophilic properties. Eur. J. Med. Chem. 2000, 35(10):923-929.
175. Luo G., Mattson G.K., Bruce M.A., Wong H., Murphy B.J., Longhi D., Antal-Zimanyi I., Poindexter G.S. Isosteric N-arylpiperazine replacements in a series of dihydropyridine NPY1 receptor antagonists. Bioorg. Med. Chem. Lett. 2004, 14(24):5975-5978.
176. Poindexter G.S., Bruce M.A., Breitenbucher J.G., Higgins M.A., Sit S.Y., Romine J.L., Martin S.W., Ward S.A., McGovern R.T., Clarke W., Russell J., Antal-Zimanyi I. Dihydropyridine neuropeptide Y Y1 receptor antagonists 2. Bioisosteric urea replacements. Bioorg. Med. Chem. 2004, 12(2):507-521.
177. 2-receptor antagonists. J. Med. Chem. 1982, 25:207-210.
178. Young R.C., Ganellin C.R., Graham M.J., Grant E.H. The dipole moments of 1,3-dimethylthiourea, 1,3-dimethyl-2-cyanoguanidine and 1,1-bis-methylamino-2-nitroethene in aqueous solution. Tetrahedron 1982, 38:1493-1497.
179. Young R.C., Ganellin C.R., Graham M.J., Roantree M.J., Grant E.H. The dielectric properties of seven polar amidine-containing compounds of biological interest. Tetrahedron Lett. 1985, 26:1897-1900.
180. Wright J.L., Gregory T.F., Kesten S.R., Boxer P.A., Serpa K.A., Meltzer L.T., Wise L.D. Subtype-selective N-methyl-d-aspartate receptor antagonists: synthesis and biological evaluation of 1-(heteroarylalkynyl)-4-benzylpiperidines. J. Med. Chem. 2000, 43:3408-3419.
181. Wu W.L., Burnett D.A., Spring R., Greenlee W.J., Smith M., Favreau L., Fawzi A., Zhang H., Lachowicz J.E. Dopamine D1/D5 receptor antagonists with improved pharmacokinetics: design, synthesis, and biological evaluation of phenol bioisosteric analogues of benzazepine D1/D5 antagonists. J. Med. Chem. 2005, 48(3):680-693.
182. Burger A. Isosterism and bioisosterism in drug design. Progr. Drug Res. 1991, 37:287-371.
183. Uloth R.H., Kirk J.R., Gould W.A., Larsen A.A. Sulfonanilides. I. Monoalkyl- and arylsulfonamidophenethanolamines. J. Med. Chem. 1966, 9(1):88-97.
184. Hacksell U., Arvidsson L.E., Svensson U., Nilsson J.L., Sanchez D., Wikstrom H., Lindberg P., Hjorth S., Carlsson A. 3-Phenylpiperidines. Central dopamine-autoreceptor stimulating activity. J. Med. Chem. 1981, 24(12):1475-1482.
185. Bhaird N.N., Fowler C.J., Thorberg O., Tipton K.F. Involvement of catechol-O-methyl transferase in the metabolism of the putative dopamine autoreceptor agonist 3-PPP(3-(3-hydroxyphenyl)-N-n-propylpiperidine). Biochem. Pharmacol. 1985, 34(19):3599-3601.
186. Jaen J.C., Wise L.D., Caprathe B.W., Tecle H., Bergmeier S., Humblet C.C., Heffner T.G., Meltzer L.T., Pugsley T.A. 4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: a novel class of compounds with central dopamine agonist properties. J. Med. Chem. 1990, 33(1):311-317.
187. Mierau J., Schneider F.J., Ensinger H.A., Chio C.L., Lajiness M.E., Huff R.M. Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur. J. Pharmacol. 1995, 290(1):29-36.
188. Schneider C.S., Mierau J. Dopamine autoreceptor agonists: resolution and pharmacological activity of 2,6-diaminotetrahydrobenzothiazole and an aminothiazole analogue of apomorphine. J. Med. Chem. 1987, 30(3):494-498.
189. van Vliet L.A., Rodenhuis N., Wikstrom H., Pugsley T.A., Serpa K.A., Meltzer L.T., Heffner T.G., Wise L.D., Lajiness M.E., Huff R.M., Svensson K., Haenen G.R., Bast A. Thiazoloindans and thiazolobenzopyrans: a novel class of orally active central dopamine (partial) agonists. J. Med. Chem. 2000, 43(19):3549-3557.
190. Blum G., Gazit A., Levitzki A. Development of new insulin-like growth factor-1 receptor kinase inhibitors using catechol mimics. J. Biol. Chem. 2003, 278(42):40442-40454.
191. Hubner H., Haubmann C., Utz W., Gmeiner P. Conjugated enynes as nonaromatic catechol bioisosteres: synthesis binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D subtype. J. Med. Chem. 2000, 43(4):756-762.
192. Lenz C., Boeckler F., Hubner H., Gmeiner P. Analogues of FAUC 73 revealing new insights into the structural requirements of nonaromatic dopamine D3 receptor agonists. Bioorg. Med. Chem. 2004, 12(1):113-117.
193. Lenz C., Haubmann C., Hubner H., Boeckler F., Gmeiner P. Fancy bioisosteres: synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel non-aromatic D3 agonist. Bioorg. Med. Chem. 2005, 13(1):185-191.
194. Street L.J., Baker R., Davey W.B., Guiblin A.R., Jelley R.A., Reeve A.J., Routledge H., Sternfeld F., Watt A.P., Beer M.S., et al. Synthesis and serotonergic activity of N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and analogues: potent agonists for 5-HT1D receptors. J. Med. Chem. 1995, 38(10):1799-1810.
195. Glen R.C., Martin G.R., Hill A.P., Hyde R.M., Woollard P.M., Salmon J.A., Buckingham J., Robertson A.D. Computer-aided design and synthesis of 5-substituted tryptamines and their pharmacology at the 5-HT1D receptor: discovery of compounds with potential anti-migraine properties. J. Med. Chem. 1995, 38(18):3566-3580.
196. Habeeb A.G., Praveen Rao P.N., Knaus E.E. Design and synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere. J. Med. Chem. 2001, 44(18):3039-3042.
197. Larson A.A., Lish P.M. A new bio-isostere: alkylsulphonamidophenethanolamines. Nature (London) 1964, 203:1283-1285.
198. Roderick S.L., Fournié-Zaluski M.C., Roques B.P., Matthews B.W. Thiorphan and retro-thiorphan display equivalent interactions when bound to crystalline thermolysin. Biochemistry 1989, 28:1493-1497.
199. Büchi J., Stünzi E., Flury M., Hirt R., Labhart P., Ragaz L. Über lokalanästhetisch wirksame basische ester und amide verschiedener alkoxy-amino-benzoesäuren. Helv. Chim. Acta. 1951, 34:1002-1013.
200. Bös M., Jenck F., Martin J.R., Moreau J.-L., Sleight A.J., Wichmann J., Widmer U. Novel agonists of 5HT2C receptors. Synthesis and biological evaluation of substituted 2-(indol-1-yl)-1-methylethylamines and 2-(indeno[1,2-b]pyrrol-1-yl)-1-methylethylamines. Improved therapeutics for obsessive compulsive disorder. J. Med. Chem. 1997, 40:2762-2769.
201. Wermuth C.G. Selective optimization of side activities: another way for drug discovery. J. Med. Chem. 2004, 47(6):1303-1314.
202. Böhm H.-J., Flohr A., Stahl M. Scaffold hopping. Drug Disc. Today Technol. 2004, 1(3):217-224.
203. Schneider G., Schneider P., Renner S. Scaffold_Hopping: how far can you jump?. QSAR Comb. Sci. 2006, 25(12):1162-1171.
204. Low C.M., Buck I.M., Cooke T., Cushnir J.R., Kalindjian S.B., Kotecha A., Pether M.J., Shankley N.P., Vinter J.G., Wright L. Scaffold hopping with molecular field points: identification of a cholecystokinin-2 (CCK2) receptor pharmacophore and its use in the design of a prototypical series of pyrrole- and imidazole-based CCK2 antagonists. J. Med. Chem. 2005, 48(22):6790-6802.
205. Huang D., Luthi U., Kolb P., Edler K., Cecchini M., Audetat S., Barberis A., Caflisch A. Discovery of cell-permeable non-peptide inhibitors of beta-secretase by high-throughput docking and continuum electrostatics calculation. J. Med. Chem. 2005, 48(16):5108-5111.
206. Steindl T.M., Crump C.E., Hayden F.G., Langer T. Pharmacophore modeling, docking, and principal component analysis based clustering: combined computer-assisted approaches to identify new inhibitors of the human rhinovirus coat protein. J. Med. Chem. 2005, 48(20):6250-6260.
207. Wilhelm M. The chemistry of polycyclic psycho-active drugs: serendipity or systematic investigation?. Pharm. J. 1975, 214:414-416.
208. Yoshimura H., Kikuchi K., Hibi S., Tagami K., Satoh T., Yamauchi T., Ishibahi A., Tai K., Hida T., Tokuhara N., Nagai M. Discovery of novel and potent retinoic acid receptor alpha agonists: syntheses and evaluation of benzofuranyl-pyrrole and benzothiophenyl-pyrrole. J. Med. Chem. 2000, 43:2929-2937.
209. Chenoweth M.B., McCarthy L.P. On the mechanism of the pharmacophoric effect of halogenation. Pharmacol. Rev. 1963, 15:673-707.
210. Goldman P. The carbon-florine bond in compounds of biological interest. Science 1969, 164:1123-1130.
211. Peters R.A. Biochemical Lesions and Lethal Synthesis 1963, Pergamon Press, Oxford.
212. Chapman N.B., James J.W., Graham J.D.P., Lewis G.P. Chemical reactivity and pharmacological activity among 2-haloethylamine derivatives with a naphtylmethyl group. Chem. Ind. (London) 1952, 805-807.
213. Vaughan J.R.J., Anderson G.W., Clapp R.C., Clark J.H., English J.P., Howard K.L., Marson H.W., Sutherland L.H., Denton J.J. Antihistamine agents. IV. Halogenated N,N-dimethyl-N'-benzyl-N-(2-pyridyl)-ethylenediamines. J. Org. Chem. 1949, 14:228-234.
214. Friedman, H. L. Antihistamine, In Influence of Isosteric Replacements upon Biological Activity, Symposium on Chemical-Biological Correlation, Washington, DC, 1951; Sciences, N. A. o., Ed. National Research Council Publication: Washington, DC, 1951; p. 295.
215. Schatz V.B. Isosterism and bioisosterism. Medicinal Chemistry 1963, 72-88. Interscience Publishers, Inc., New York. A. Burger (Ed.).
216. Fessenden R.J., Fessenden J.S. The biological properties of silicon compounds. Advances in Drug Research 1967, Vol. 4:95-132. Academic Press, London. N.J. Harper, A.B. Simmonds (Eds.).
217. Tacke R., Zilch H. Sila-substitution-a useful strategy for drug design?. Endeavour, New Series 1986, 10:191-197.
218. Tacke R., Zilch H. Drug-design by sila-substitution and microbial transformations of organosilicon compounds: some recent results. L'Actualité Chimique 1986, 75-82.
219. Ricci A., Seconi G., Taddei M. Bioroganosilicon chemistry: trends and perspectives. Chimica Oggi-Chemistry Today 1989, 7:15-21.
220. Showell G.A., Mills J.S. Chemistry challenges in lead optimization: silicon isosteres in drug discovery. Drug Disc. Today 2003, 8(12):551-556.
221. Zifrosilone. Drugs Fut. 1994, 19:854-855. Anonymous.
222. Hornsperger J.-M., Collard J.-N., Heydt J.G., Giacobini E., Funes S., Dow J., Schirlin D. Trimethylsilylated trifluoromethyl ketones, a novel class of acetylcholinesterase inhibitors: biochemical and pharmacological profile of MDL 73,745. Biochem. Soc. Trans. 1994, 22:758-763.
223. Metcalf R.L., Fukuto T.R. Silicon-containing carbamate insecticides. J. Econ. Entomol. 1965, 58:1151.
224. Fessenden R.J., Coon M.D. Silicon-substituted medicinal agents. Silacarbamates related to meprobamate. J. Med. Chem. 1965, 8:604-608.
225. Tacke R. Sila-Pharmaka, XIX. Sila-Pridinol und Pridinol: Darstellung und Eigenschaften sowie Strukturen im kristallinen und gelösten Zustand. Chem. Ber. 1980, 113:1962-1980.
226. Moberg, W. K. Fungicidal 1,2,3-triazole derivatives. US Patent 4,510,136 (Apr. 9, 1985 to E.I. Du Pont de Nemours & Co) 1985.
227. 2A antagonists. Bioorg. Med. Chem. Lett. 1994, 4:415-420.
228. Gotteland J.-P., Brunel I., Gendre F., Désiré J., Delhon A., Junquéro D., Oms P., Halazy S. (Aryloxy)methylsilane derivatives as new cholesterol biosynthesis inhibitors: synthesis and hypocholesterolemic activity of a new class of squalene epoxidase inhibitors. J. Med. Chem. 1995, 38:3207-3216.
229. Gotteland J.-P., Delhon A., Junquéro D., Oms P., Halazy S. Design and synthesis of new hypocholesteremic organosilanes with antioxidant properties. Bioorg. Med. Chem. Lett. 1996, 6:533-538.
230. Heinonen P., Sipilä H., Neuvonen K., Lönnberg H., Cockroft V.B., Wurster S., Virtanen R., Savola M.K.T., Salonen J.S., Savola J.M. Synthesis and pharmacological properties of 4(5)-(2-ethyl-2,3-dihydro-2-silainden-2-yl)imidazole, a silicon analogue of atipamezole. Eur. J. Med. Chem. 1996, 31:725-729.
231. Bom D., Curran D.P., Kruszewski S., Zimmer S.G., Strode J.T., Kohlhagen G., Du W., Chavan A.J., Fraley K.A., Bingcang A.L., Latus L.J., Pommier Y., Burke T.G. The novel silatecan 7-tert-butyldimethylsilyl-10-hydroxycamptothecin displays high lipophilicity, improved human blood stability, and potent anticancer activity. J. Med. Chem. 2000, 43:3970-3980.
232. Mutahi M., Nittoli T., Guo L., Sieburth S.M. Silicon-based metalloprotease inhibitors: synthesis and evaluation of silanol and silanediol peptide analogues as inhibitors of angiotensin-converting enzyme. J. Am. Chem. Soc. 2002, 124(25):7363-7375.
233. Chen C.A., Sieburth S.M., Glekas A., Hewitt G.W., Trainor G.L., Erickson-Viitanen S., Garber S.S., Cordova B., Jeffry S., Klabe R.M. Drug design with a new transition state analog of the hydrated carbonyl: silicon-based inhibitors of the HIV protease. Chem. Biol. 2001, 8(12):1161-1166.
234. Showell G.A., Barnes M.J., Daiss J.O., Mills J.S., Montana J.G., Tacke R., Warneck J.B. (R)-sila-venlafaxine: a selective noradrenaline reuptake inhibitor for the treatment of emesis. Bioorg. Med. Chem. Lett. 2006, 16(9):2555-2558.
235. Barnes M.J., Conroy R., Miller D.J., Mills J.S., Montana J.G., Pooni P.K., Showell G.A., Walsh L.M., Warneck J.B. Trimethylsilylpyrazoles as novel inhibitors of p38 MAP kinase: a new use of silicon bioisosteres in medicinal chemistry. Bioorg. Med. Chem. Lett. 2007, 17(2):354-357.
236. Sommer L.H., Bennet O.F., Campbell P.G., Weyenberg D.R. Stereochemistry of hydride ion displacement from silicon. Enhanced rates at bridgehead and 4-ring silicon atoms. J. Amer. Chem. Soc. 1957, 79:3295-3296.
237. Alam F., Soloway A.H., Bapat B.V., Barth R.F., Adams D.M. Boron compounds for neutron capture therapy. Basic Life Sci. 1989, 50:107-111.
238. Gabel D. Tumor-seeking for boron neutron capture therapy: synthesis and biodistribution. Basic Life Sci. 1989, 50:233-241.
239. Kahl S.B., Joel D.D., Finkel G.C., Micca P.L., Nawrocky M.M., Coderre J.A. A carboranyl porphyrin for boron neutron capture therapy of brain tumors. Basic Life Sci. 1989, 50:193-203.
240. Caujolle F., Chan Pham.-Huu. Structure Chimique et Activité Spasmolytique des Organoboriques. Arch. Int. Pharmacodyn. Ther. 1968, 172:467-474.
241. Mubarak S.I.M., Stanford J.B., Sugden J.K. Some aspects of the antimicrobial and chemical properties of phenyl boronate esters of chloramphenicol. Drug Dev. Ind. Pharm. 1984, 10:1131-1160.
242. Hutter R., Keller-Schierlein W., Knusel F., Prelog V., Rodgers G.C., Suter P., Vogel G., Voser W., Zahner H. The metabolic products of microorganisms. Boromycin. Helv. Chim. Acta. 1967, 50(6):1533-1539.
243. Dünitz J.D., Hawley D.M., Miklos D., White D.N.J., Berlin Y., Marusik R., Prelog V. Structure of boromycin. Helv. Chim. Acta. 1971, 54:1709-1713.
244. Okami Y., Okazaki T., Kitahara T., Umezawa H. Studies on marine microorganisms. V. A new antibiotic, aplasmomycin, produced by a streptomycete isolated from shallow sea mud. J. Antibiot. (Tokyo) 1976, 29(10):1019-1025.
245. Kinder D.H., Katzenellenbogen J.A. Acylamino boronic acids and difluoroborane analogues of amino acids: potent inhibitors of chymotrypsine and elastase. J. Med. Chem. 1985, 28:1917-1925.
246. Adams J., Behnke M., Chen S., Cruickshank A.A., Dick L.R., Grenier L., Klunder J.M., Ma Y.T., Plamondon L., Stein R.L. Potent selective inhibitors of the proteasome: dipeptidyl boronic acids. Bioorg. Med. Chem. Lett. 1988, 8(4):333-338.
247. Dembitsky V.M., Srebnik M. Synthesis and biological activity of α-aminoboronic acids, amine-carboxyboranes and their derivatives. Tetrahedron 2003, 59(5):579-593.
248. Surolia N., RamachandraRao S.P., Surolia A. Paradigm shifts in malaria parasite biochemistry and anti-malarial chemotherapy. Bioessays 2002, 24(2):192-196.
249. Jabbour A., Steinberg D., Dembitsky V.M., Moussaieff A., Zaks B., Srebnik M. Synthesis and evaluation of oxazaborolidines for antibacterial activity against streptococcus mutans. J. Med. Chem. 2004, 47(10):2409-2410.
250. Kumar S.K., Hager E., Pettit C., Gurulingappa H., Davidson N.E., Khan S.R. Design, synthesis, and evaluation of novel boronic-chalcone derivatives as antitumor agents. J. Med. Chem 2003, 46(14):2813-2815.
251. Landauer W. On the chemical production of developmental abnormalities and of phenocopies in chicken embryos. J. Cell. Comp. Physiol. 1954, 43(1):261-305.
252. Landauer W., Clark E.M. On the role of riboflavin in the teratogenic activity of boric acid. J. Expt. Zool. 1964, 156:307-312.
253. Browning E. Toxicity of Industrial Metals 1969, Appleton-Century-Crofts, New York, p. 90-97. 2nd ed.
254. Klayman D.L., Günther W.H.H. Organic Selenium Compounds: Their Chemistry and Biology 1973, Wiley-Interscience, New York.
255. Kang S.-I., Spears C.P. Linear free energy relationships and cytotoxicities of para-substituted 2-haloethyl aryl selenides and bis(-chloroethyl) selenides. J. Med. Chem. 1987, 30:597-602.
256. Fischer H., Terlinden R., Löhr J.P., Römer A. A novel biologically active selenoorganic compound. VIII. Biotransformation of ebselen. Xenobiotica 1988, 18:1347-1359.
257. Parnham M.J., Graf E. Seleno-organic compounds and the therapy of hydroperoxide-linked pathological conditions. Biochem. Pharmacol. 1987, 36:3095-3102.