2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes

Current Medicinal Chemistry

Volumn 12, Issue 7, 2005, Pages 877-885

  Poupaert, Jacques ^a   Carato, Pascal ^b   Colacino, Evelina ^a  

^a UNIVERSITY OF LOUVAIN MEDICAL SCHOOL   (Belgium)

^b Faculté des Sciences Pharmaceutiques et Biologiques Université de Lille   (France)

Author keywords

2(3H) benzothiazolinone; 2(3H) benzoxazolone; Bioisosterism; Mixed affinity ligands; Privileged scaffolds

Indexed keywords

10194 CERM; 2 BENZOXAZOLONE DERIVATIVE; 6 METHOXY 2 BENZOXAZOLONE; AMPHETAMINE; ANALGESIC AGENT; ANTICONVULSIVE AGENT; ANTIFUNGAL AGENT; ANTIINFLAMMATORY AGENT; BENZIMIDAZOL 2 ONE; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLINE DERIVATIVE; BENZOXAZINONE DERIVATIVE; BENZOYL 2 BENZOXAZOLONE; CATECHOL; CHLORZOXAZONE; DOPAMINE 2 RECEPTOR; DOPAMINE 4 RECEPTOR; HETEROCYCLIC COMPOUND; NEUROLEPTIC AGENT; NEUROPROTECTIVE AGENT; OXINDOLE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; PHENOL; S 14080; SEROTONIN 1A RECEPTOR; SEROTONIN 2A RECEPTOR; SIGMA 1 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR; SIGMA OPIATE RECEPTOR; TOPICAL ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINIZENE;

CHEMICAL REACTION; CLINICAL TRIAL; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; ELECTRICITY; EXTRAPYRAMIDAL SYMPTOM; HUMAN; LIGAND BINDING; PARKINSONISM; RECEPTOR AFFINITY; REVIEW; TARDIVE DYSKINESIA;

BENZOXAZOLES; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR PROBES; MOLECULAR STRUCTURE;

EID: 15444374352     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867053507388     Document Type: Review

References (107)

1. For general readings on Privileged scaffolds see: (a) De Simone, R.W.; Currie, K.S.; Mitchell, S.A.; Darrow, J.W.; Pippin, D.A. Comb. Chem. & High Throughput Screening, 2004, 7(5), 473-494;
2. (b) Triggle, D. Cell. Mol. Biol., 2003, 23 3), 293-303.
3. For general readings on Bioisosterism see: (a) Olesen, P.H. Curr. Opin. Drug Discov. Devel., 2001, 4, 471-8;
4. (b) Patani, G. A.; Edmond, J.; LaVoie, E. J. Chem Rev., 1996, 96, 3147-3176;
5. (c) Fujita, T. Biosci. Biotech. Biochem., 1996, 60(4), 557-566;
6. (d) Cramer, R.D.; Clark, R.D.; Patterson, D.E.; Ferguson, A.M. J. Med. Chem., 1996, 39, 3060-9;
7. (e) Burger, A. Prog. Drug. Res., 1991, 37, 287-371;
8. (f) Liljefors, T.; Jorgensen, F.S.; Krogsgaard-Larsen, P. Rational molecular design in drug research. Copenhagen (Denmark), Munksgaard, 1998. P. 400, ISBN 87-16-12049-3.
9. For recent applications of bioisosterism see: (a) Lima, P.C.; Avery, M.A.; Tekwani, B.L.; de Alves, H.M.; Barreiro, E.J.; Fraga, C.A. Farmaco, 2002, 57, 825-32;
10. (b) Hwang, K.J.; Lee, T.S.; Kim, K.W.; Kim, B.T.; Lee, C.M.; Park, E.Y.; Woo, R.S. Arch. Pharm. Res., 2001, 24, 270-5;
11. (c) McCurdy, C.R.; Jones, R.M.; Portoghese, P.S. Org. Lett., 2000, 2(6), 819-21;
12. (d) Bhattacharjee, A.K.; Gupta, R.K.; Ma, D.; Karle, J.M. J. Mol. Recognit., 2000, 13(4), 213-220.
13. Groenwik, H. Bull. Soc. Chim., 1876, 25, 178.
14. Sandmeyer, G. Ber., 1886, 19, 2656.
15. Graebe, J.; Rostovzew, S. Ber., 1902, 35, 2751.
16. Lespagnol, Ch.; Cazin, J.C.; Cazin, M.; Lesieur, D.; Dupont, C. Bull. Chim. Therap., 1967, 5, 347.
17. Tacquet, A.; Lespagnol, Ch.; Beerens, H.; Lesieur, D.; Devulder, B. Ann. Inst. Pasteur Lille, 1971, 22, 189.
18. Cazin, J.C.; Lesieur, D.; Lespagnol, Ch.; Cazin, M.; Lemaire, P.; Brunet, C. Eur. J. Med. Chem., 1976, 11, 33.
19. Lespagnol, A.; Lefebvre-Cannesson, J.C. R. Soc. Biol., 1944, 138, 529.
20. Lespagnol, A.; Lespagnol, Ch.; Lesieur, D.; Marcincal-Lebebvre, A.; Dupont, C. Bull. Chim. Ther., 1967, 5, 343.
21. Shieh, W.-C.; Lozanov, M.; Loo, M.; Repic, O.; Thomas, J. Tetrahedron Letters, 2003, 44(24), 4563-4565.
22. Fu, Y.; Baba, T.; Ono, Y. J. of Catalysis, 2001, 197(1), 91.
23. Zinner, H.; Herbig, H.; Wigert, H. Chem. Ber., 1956 89, 2131.
24. Zinner, H.; Randow, F.; Wigert, H. J. Prakt. Chem., 1966, 33, 130.
25. Atkinson, R. S.; Rees, C.W. Chem. Commun., 1967, 23, 1230-1.
26. Lespagnol Ch. Bull. Soc. Pharm., 1955, 1, 71.
27. Bonte, J.P.; Lesieur, D.; Lespagnol, Ch.; Cazin, J.C.; Cazin, M. Eur. J. Med. Chem., 1974, 9, 491.
28. Bonte, J.P.; Lesieur, D.; Lespagnol, Ch.; Cazin, J.C.; Cazin, M. Eur. J. Med. Chem., 1974, 9, 497.
29. Merdji, B.; Lesieur, D.; Lespagnol, Ch.; Barbry, D.; Couturier, D. J. Heterocyclic Chem., 1981, 18, 1223.
30. Aichaoui, H.; Poupaert, J.H.; Lesieur, D.; Henichart, J.P. Tetrahedron, 1991, 47, 6649.
31. Aichaoui, H.; Lesieur, D.; Henichart, J.P. J. Heterocyclic Chem., 1992, 29, 171.
32. Aichaoui, H.; Poupaert, J.H.; Lesieur, D.; Henichart, J.P. Bull. Soc. Chim. Belg., 1992, 101, 1053.
33. Yous, S.; Poupaert, J.H.; Lesieur, I.; Depreux, P.; Lesieur D. J. Org. Chem., 1994, 59, 1574.
34. Poupaert, J.H.; Kanyonyo, M.; Ucar, H.; Mouithys-Mickalad, A.; Diouf, O.; Lesieur, D. Bull. Soc. Chim. Belg., 1996, 105, 397.
35. Taverne, T.; Depreux, P.; Lesieur, D.; Henichart, J.P.; Poupaert, J.H. Bull. Soc. Chim. Belg., 1997, 106, 791.
36. Ucar, H.; Van Derpoorten, K.; Debovere, P.; Lesieur, D.; Isa, M.; Masereel, B.; Delarge, J.; Poupaert, J.H. Tetrahedron, 1998 54, 1763.
37. Liacha, M.; Yous, S.; Poupaert, J.H.; Depreux, P.; Aichaoui H. Monatsh. Chem., 1999, 130, 1393.
38. Mésangeau, C.; Poupaert, J.H.; Carato, P.; Yous, S. Heterocycles, 2003, 60(12), 2621.
39. Bower, P.; Stephens, Y. J. Chem. Soc., 1951, 325.
40. Mustafa, A.; Asker, W.; Hishmat, O.H. J. Amer. Chem. Soc. 1955, 77, 5127.
41. Lespagnol, A.; Mercier, J.; Sestier, R.; Marinacce, P. Bull. Soc. Chim. Biol., 1952, 34, 397.
42. Lespagnol, A.; Mercier, J.; Lespagnol, Ch. Arch. Internat. Ther., 1953, 94, 211.
43. Lespagnol, A.; Vincent, M.; Lespagnol, Ch. Bull. Soc. Pharm., 1953, 1, 35.
44. Lespagnol, A.; Warembourg, H.; Lespagnol, Ch.; Butaeye, P. Lille-Médical, 1951, 6, 8.
45. Lespagnol, A.; Durbet, F.; Mongy, J. Bull. Soc. Biol. Lille, 1941, 135, 1255.
46. Lespagnol, A.; Lefebvre, J. Bull. Soc. Chim., 1945 386.
47. Bonte, J.P.; Lesieur, D.; Plat, M.; Cazin, J.C.; Cazin, M.; Lespagnol Ch. Eur. J. Med. Chem., 1974, 9, 491.
48. Renard, P.; Lesieur, D.; Lespagnol, C.; Cazin, M.; Brunet, C.; Cazin, J.C. Eur. J. Med. Chem., 1980, 15, 453.
49. Mairesse, G.; Boivin, J.C.; Thomas, D.J.; Bermann, M.C.; Bonte, J.P.; Lesieur, D. Acta Crysta., 1984, 40, 1019.
50. Follet, C.; Boivin, J.C.; Bonte, J.P.; Lesieur, D. Acta Crysta., 1991, 47, 882.
51. Ferriera, S.H.; Lorenzetti, B.B.; Devissaguet, M.; Lesieur, D.; Tsouderos, Y. British J. Pharm., 1995, 114(2), 303-8.
52. Yous, S.; Poupaert, J.-H.; Chavatte, P.; Espiard, J.-G.B.; Caignard, D.-H.; Lesieur, D. Drug Design and Discovery, 2001, 17(4), 331-336.
53. Van derpoorten, K.; Ucar, H.; Andrei, G.; Snoeck, R.; Balzarini, J.; De Clercq, E.; Poupaert, J.H. Antiviral Chem. Chemotherapy, 1999, 10(2), 87-97.
54. Dogruer, D.S.; Ünlü, S.; Sahin, M.F.; Yqilada, E. Il Farmaco, 1998, 53(1), 80.
55. Si-Nang, L.; Simond, J.; Schiff, V.; Trottier, D.; Pourrat, A. Pharm. Acta Helv., 1985, 60(4), 112-6.
56. Wang, H.X.; Ng, T.B. Comparative Biochemistry and Physiology, Part C/ Toxicology & Pharmacology, 2002, 132C 2), 261-268.
57. Lesieur, D.; Lespagnol, Ch.; Vaccher, M.P.; Bonte, J.P.; Debaert, M.; Busch, N.; Combourieu, M. Brevet Français, 1980 80-20861.
58. Bonte, J.P.; Piancastelli, M.C.; Lesieur, I.; Lamar, J.C.; Beaughard, M.; Dureng, G. Eur. J. Med. Chem., 1990, 25, 361.
59. Vaccher, M.P.; Lesieur, D.; Bonte, J.P.; Lamar, J.C.; Beaughard, M.; Dureng, G.; Lespagnol, C. Il Farmaco Ed. Sci., 1986, 41, 257.
60. Mairesse, G.; Boivin, J.C.; Thomas, D.J.; Bonte, J.P.; Lesieur, D.; Lespagnol, Ch. Acta Cryst. C., 1984, 40, 1432.
61. Auer, J.; Berent, R.; Weber, T.; Ng, C.K.; Lassnig, E.; Lamm, G.; Eber, B. Current Medicinal Chemistry: Cardiovascular & Hematological Agents, 2004, 2(1), 29-34.
62. Roubert, C.; Spielewoy, C.; Soubrie, P.; Hamon, M.; Giros, B.; Betancur, C. Neuroscience, 2004, 123(2), 537-546.
63. Menegatti, R.; Cunha, A.C.; Ferreira, V.F.; Barreiro, E.J. Bioorg. Med. Chem., 2003, 11(22), 4807.
64. Huttunen, M. J. Clin. Psychopharmacol., 1995, 15, 45.
65. Santanavanich, C.; Chetsawang, B.; Ebadi, M.; Govitrapong, P. Journal of Pineal Research, 2003, 35(3), 169-176.
66. Collard, J. Rev. Can. Biol., 1961, 20, 465.
67. Harrigan, E.P.; Miceli, J.J.; Anziano, R.; Watsky, E.; Reeves, K.R.; Cutler, N.R.; Sramek, J.; Shiovitz, T.; Middle, M. Journal of Clinical Psychopharmacology, 2004, 24(1), 62-69.
68. Carlson, C.D.; Cavazzoni, P.A.; Berg, P.H.; Wei, H.; Beasley, C.M.; Kane, J.M. Journal of Clinical Psychiatry, 2003, 64 8), 898-906.
69. Bersani, G.; Grispini, A.; Marini, S.; Pasini, A.; Valducci, M.; Ciani, N. Clin. Pharmacol., 1990, 13, 500.
70. Blin, O.; Azorin, J.M.; Bouhours, P. J. Clin. Psychopharmacol., 1996, 16, 38S.
71. Reyntjens, A.; Gelders, Y.G.; Hoppenbrouwers, M.L.J.A.; Vanden Bussche, G. Drug Dev. Res., 1988, 8, 205.
72. Brunello, N.; Masotto, C.; Steardo, L.; Markstein, R.; Racagni, G. Neuropsychopharmacol., 1995, 13, 177.
73. Wagstaff, A.J.; Bryson, H.M. CNS Drugs, 1995, 4, 370.
74. Doat, M.M.; Rabin, R.A.; Winter, J.C. Int. J. Neuropsychopharmacology, 2002, 5(2), 153-158.
75. Meltzer, H.Y. Current Opinion in Pharmacology, 2004 4(1), 53-57.
76. Friedman, J.H. Psychoneuroendocrinology, 2002, Volume Date 2003, 28(Suppl. 1), 39-51.
77. Huttunen, J.; Kaehkoenen, S.; Kaakkola, S.; Ahveninen, J.; Pekkonen, E. NeuroReport, 2003, 14(12), 1609-1612.
78. Lesieur, D.; Lespagnol, Ch.; Caignard, D.H.; Busch, N. Brevet Europeen, 83-402267-5, 1983.
79. Caignard, D.H.; Lespagnol, Ch.; Lesieur, D.; Busch, N. U.S. P 4,558,060, 1985.
80. Caignard, D.H.; Couquelet ,J.; Lesieur, D.; Lespagnol, C.; Lamar, J.C.; Beaughard, M.; Leinot, M. Il Farmaco Ed. Sci., 1985 40, 854.
81. Boivin, M.J.; Boivin, J.C.; Bonte, J.P.; Lesieur, D. Acta Cryst. C., 1987, 43, 1721.
82. Taverne, T.; Lesieur, D.; Depreux, P.; Caignard, D.H.; Guardiola-Lemaître, B.; Adam, G.; Renard, P. Brevet Français, 94-03300, 1994.
83. Diouf, O.; Depreux, P.; Lesieur, D.; Poupaert; J.H.; Caignard, D.H. Eur. J. Med. Chem., 1995, 30, 715.
84. Taverne, T.; Diouf, O.; Depreux, P.; Poupaert, J.; Lesieur, D.; Guardiola-Lemaître, B.; Renard, P.; Rettori, M.C.; Caignard, D.H. J. Med. Chem., 1998, 41, 2010.
85. Diouf, O.; Carato, P.; Depreux, P.; Bonte, J.P.; Caignard, D.H.; Guardiola-Lemaitre, B.; Rettori, M.C.; Belzung, C.; Lesieur, D. Bioorg. Med. Chem., 1997, 7, 2579.
86. Diouf, O.; Carato, P.; Lesieur, I.; Rettori, M.C.; Caignard, D.H. Eur. J. Med. Chem., 1999, 34, 69.
87. Diouf, O.; Poupaert, J.H.; Salim, M.; Lesieur, D.; Isa, M. Saudi Pharm. J., 2000, 8, 91.
88. Uphouse, L.; White, S.; Harrison, L.; Hiegel, C.; Majumdar, D.; Guptarak, J.; Truitt, W.A. Pharmacology, Biochemistry and Behavior 2003, 76(1), 63-73.
89. Zhang, Y.; Laster, M.J.; Eger, E.I.; II; Stabernack, C.R.; Sonner, J.M. Anesthesia & Analgesia, 2003, 97(2), 475-479.
90. Ucar, H.; Cacciaguerra, S.; Spampinato, S.; Van derpoorten, K.; Isa, M.; Kanyonyo, M.; Poupaert, J.H. Eur. J. Pharmacology, 1997, 335(2/3), 267-273.
91. Jayyosi, Z.; McGeehan, G.; Kelley, M.; Labaudiniere, R.; Zhang, L.; Groneberg, R. International patent, 2000, WO 00/64888.
92. Jayyosi, Z.; McGeehan, G.; Kelley, M.; Labaudiniere, R.; Zhang, L.; Caulfield, T.; Minnich, A.; Bobko, M. International patent 2000, WO 00/64876.
93. Panigrahy, D.; Shen, L.Q.; Kieran, M.W.; Kaipainen, A. Expert Opinion on Investigational Drugs, 2003, 12(12), 1925-1937.
94. Burris, T.P.; Combs, D.W.; Rybczynski, P.J. PCT Int. Appl 2001, 76 pp. WO 2001087862.
95. Burris, T.P.; Combs, D.W.; Rybczynski, P.J.; Dudash, J. U.S. Pat. Appl. Publ., 2003, 35 pp., Cont.-in-part of U. S. Ser. No. 854,302. US 2003083329.
96. Lesieur, D.; Blanc-Delmas, E.; Yous, S.; Depreux, P.; Guillaumet, G.; Dacquet, C.; Levens, N.; Boutin, J.A.; Bennejean, C.; Renard, P. PCT Int. Appl. 2001, 67 pp. WO 2001057002.
97. Galet, V.; Bernier, J.-L.; Henichart, J.-P.; Lesieur, D.; Abadie, C.; Rochette, L.; Lindenbaum, A.; Cnalas, J.; Renaud de la Faverie, J.-F. J. Med. Chem., 1994, 37(18), 2903-11.
98. McNutt, R.W., Jr.; Jung, D.K.; Harris, P.A.; Hunter, R.N., III; Veal, J.M.; Dickerson, S.; Lackey, K.E.; Peel, M.R. PCT Int. Appl., 1999, 144 pp. WO 9910325, AN 1999:166598
99. Viaud, M.C.; Jamoneau, P.; Bizot-Espiard, J.G.; Pfeiffer, B.; Renard, P.; Caignard, D.H.; Adam, G.; Guillaumet, G. Bioorg. Med. Chem., 1995, 3(7), 929-37.
100. Viaud, M.-C.; Jamoneau, P.; Flouzat, C.; Bizot-Espiard, J.-G.; Pfeiffer, B.; Renard, P.; Caignard, D.-H.; Adam, G.; Guillaumet, G. J. Med. Chem., 1995, 38(8), 1278-86.
101. Onkol, T.; Dogruer D.S.; Ito, S.; Sahin, M.F. Arch. Pharm. (Weinheim), 2000, 333, 337-40.
102. Mizoguchi, T.; Nishinaka, T.; Uchida, G.; Mizuta, J.; Uchida, H.; Terada, T.; Toya, H. Biol. & Pharm. Bulletin, 1993, 16 9), 840-2.
103. Ahmad, R.; Kookana, R.S.; Alston, A.M.; Skjemstad, J.O. Environ. Sci. Technol., 2001, 35, 878-84.
104. Sanusi, A.; Millet, M.; Mirabe, P.; Wortham, H. Sci. Total Environ., 2000, 263, 263-77.
105. Venugopal, V.; Naidu, V.G.; Prasad, P.R. Pestology, 2003, 27(4), 29-34.
106. Lee, M.-G. Food Science and Biotechnology, 2002, 11 6), 690-693.
107. Banasik, M.; Stedeford, T.; Persad, A.S.; Ueda, K.; Tanaka, S.; Muro-Cacho, C.; Harbison, R.D. J. Enzyme Inhibit. Med. Chem., 2003, 18(6), 551-555.