Chemoenzymatic synthesis of enantiopure 1,4-dihydropyridine derivatives

Biocatalysis and Biotransformation

Volumn 22, Issue 4, 2004, Pages 231-252

  Sobolev, A ^a,b   Franssen, Maurice C R ^a   Duburs, G ^b   De Groot, A E ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

Author keywords

Asymmetrisation; Enantiopure 1,4 dihydropyridines; Enzyme catalysed hydrolysis; Kinetic resolution; Transesterification

Indexed keywords

CALCIUM; CARBOXYLIC ACIDS; CELLS; DERIVATIVES; DRUG PRODUCTS; ENZYMES; FLUXES; HYDROLYSIS; ORGANIC SOLVENTS;

CHEMOENZYMATIC SYNTHESIS; ENANTIOPURE DRUGS; ENZYMATIC TRANSFORMATIONS; ORGANIC COSOLVENTS;

BIOSYNTHESIS;

1,4 DIHYDROPYRIDINE DERIVATIVE; 4 ARYL 2,6 DIMETHYL 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLIC ACID; AMLODIPINE; ANTIANGINA PECTORIS AGENT; ANTIHYPERTENSIVE AGENT; BENIDIPINE; CALCIUM ANTAGONIST; CALCIUM CHANNEL BLOCKING AGENT; CALCIUM CHANNEL STIMULATING AGENT; CARBOXYLIC ACID DERIVATIVE; DRUG ANALOG; FELODIPINE; HYDROLASE; LERCANIDIPINE; MANIDIPINE; MEPIRODIPINE; NICARDIPINE; NIFEDIPINE; NILVADIPINE; NIMODIPINE; NITRENDIPINE; ORGANIC SOLVENT; PYRIDINE DERIVATIVE; RIODIPINE; SODIUM SULFIDE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ASYMMETRIC CATALYSIS; BIOCATALYST; CARDIOVASCULAR DISEASE; CHIRALITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENZYME CHEMISTRY; HUMAN; PROCESS OPTIMIZATION; REVIEW; STEREOCHEMISTRY; TEMPERATURE; TRANSESTERIFICATION;

EID: 11244251882     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.1080/10242420400009939     Document Type: Review

References (104)

1. Aboul-Enein, H.Y and Wainer, I.W. (1997) The impact of stereochemistry on drug development and use (John Wiley & Sons).
2. Achiwa, K. and Kato, T. (1999) Asymmetric synthesis of optically active 1,4-dihydropyridines as calcium antagonists, Curr. Org. Chem. 3, 77-106.
3. Adachi, T., Ishii, M., Ohta, Y., Ota, T., Ogawa, T. and Hanada, K. (1993) Chemoenzymatic synthesis of optically active 1,4-dihydropyridine derivatives via enantioselective hydrolysis and transesterification, Tetrahedron: Asymmetry 4, 2061-2068.
4. Alajarin, R., Vaquero, J.J., Alvarez-Builla, J., Pastor, M., Sunkel, C., Fau de Casa-Juana, M., Priego, J., Statkow, P.R., Sanz-Aparicio, J. and Fonseca, I. (1995) Synthesis, structure, and pharmaceutical evaluation of stereomers of furnidipine, J. Med. Chem. 38, 2830-2841.
5. Ashimori, A., Uchida, T., Ohtaki, Y., Tanaka, M., Ohe, K., Fukaya, C., Watanabe, M., Kagitani, M. and Yokoyama, K. (1991) Synthesis and pharmacological effects of optically active 2-(4-(4-benzhydryl-1-piperazinyl)phenyl)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate hydrochloride, Chem. Pharm. Bull. 39, 108-111.
6. Beudeker, H.J., van der Velden, J.W. and van der Aar, E.M. (2000) Interaction profile and tolerability of barnidipine, Int. J. Clin. Pract. Suppl. 114, 36-40.
7. Bird, G.L., Prach, A.T., McMahon, A.D., Forrest, J.A., Mills, P.R. and Danesh, B.J. (1998) Randomised controlled double-blind trial of the calcium channel antagonist amlodipine in the treatment of acute alcoholic hepatitis, J. Hepatol. 28, 194-198.
8. Bisenieks, E.A., Uldrikis, J.R., Kirule, I.E., Tirzit, G.D. and Dubur G.J. (1982) Synthesis and antioxidant activities of 2-methyl-5-oxo-1,4-dihydroindeno(1,2-b)pyridines. Khim. Geterotsikl. Soed. 1528-1531.
9. Bossert, F. and Vater, W. (1971) Dihydropyridines, a new group of strongly effective coronary therapeutic agents, Naturwissenschaften 58, 578.
10. Briede, J., Daija, D., Stivrina, M. and Duburs, G. (1999) Effect of cerebrocrast on lymphocyte blast transformation activity in normal and streptozotocin induced diabetic rats, Cell. Biochem. Func. 17, 89-96.
11. Caballero, E., Puebla, P., Sanchez, M., Medarde, M., del Prado, L.M. and Feliciano, A.S. (1996a) Enantiospecific synthesis of dihydropyridines from chiral enamines, Tetrahedron: Asymmetry 7, 1985-1994.
12. Caballero, M., Puebla, P., Medarde, M., Sanchez, M., Salvado, M.A., Garcia-Granda, S. and San Feliciano, A. (1996b) Synthesis of enantiopure 2,3,8,8a-tetrahydro-7h-oxazolo(3,2a)pyridine derivatives, J. Org. Chem. 61, 1890-1893.
13. Caccamese, S., Chillemi, R. and Principato, G. (1996) Fluorenone 1,4-dihydropyridine derivatives with cardiodepressant activity: enantiomeric separation by chiral HPLC and conformational. aspects, Chirality 8, 281-290.
14. Chekavichus, B.S., Sausins, A.E. and Dubur, G.J. (1982) Effect of substituents in the dihydropyridine ring on the reactivity of the ester group of 3,5-dialkoxycarbonyl-1,4-dihydropyridines. Khim. Geterotsikl. Soed. 1072-1077.
15. Chekavichus, B.S., Sausins, A.E., Zolotoyabko, R.M. and Dubur, G.J. (1985) 2,6-Di(aryl)-3,5-dialkoxycarbonyl-1,4-dihydropyridines. Latvijas PSR ZA vestis, Chem. ser. 77-85.
16. Chen, C.S., Fujimoto, Y, Girdaukas, G. and Sih, C.J. (1982) Quantitative analyses of biochemical kinetic resolution of enantiomers, J. Am. Chem. Soc. 104, 7294-7299.
17. Cheng, C.Y., Chen, J.Y. and Lee, MJ. (1996) An asymmetric synthesis of 4-aryl-1,4-dihydropyridines, Heterocycles 43, 2425-2434.
18. Daniels, J.M.D., Nestmann, E.R. and Kerr, A. (1997) Development of stereoisomeric (chiral) drugs: a brief review of scientific and regulatory considerations, Drug Inf. J. 31, 639-646.
19. de Castro, M.S., Salazar, L. and Sinisterra, J.V. (1997) Influence of the N-MOM group in the enantioselective lipase catalyzed methanolysis of racemic 1,4-dihydropyridine dicarboxylates, Tetrahedron: Asymmetry 8, 857-858.
20. Ebiike, H., Maruyama, K. and Achiwa, K. (1992a) Enzymatic synthesis of optically active 2-carbamoyloxymethyl-1,4-dihydropyridines, (R)-( + )- and (S)-( - )-NB 818, Tetrahedron Lett. 3, 1153-1156.
21. Ebiike, H., Maruyama, K. and Achiwa, K. (1992b) Lipase-catalyzed enantioselective hydrolysis of 4-alkyl-1,4-dihydropyridine derivatives: synthesis of ( + )- and ( - )-methyl 2-(phenylthio)ethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate (PCA 4248), Chem. Pharm. Bull. 40, 1083-1085.
22. Ebiike, H., Maruyama, K., Ozawa, Y., Yamazaki, Y. and Achiwa, K. (1997a) Asymmetric synthesis of (R)-nilvadipine and (S -NB 818 via regioselective bromination of chiral 1,4-dihydropyridines as a key step and enzymatic resolution of racemic 2-hydroxymethyl-1,4-dihydropyridine derivatives, Chem Pharm. Bull. 45, 869-876.
23. Ebiike, H., Maruyama, K., Yamazaki, Y., Hirose, Y., Kariya, K., Sasaki, I., Kurono, Y., Terao, Y. and Achiwa, K. (1997b) Lipase-catalyzed enantioselective hydrolysis of bis(acyloxymethyl) 1,4-dihydro-3,5-pyridinedicarboxylates leading to optically active medicines, Chem. Pharm. Bull. 45, 863-868.
24. Ebiike, H., Ozawa, Y., Achiwa, K., Hirose, Y., Kariya, K., Sasaki, I. and Kurono, Y. (1993) Enzyme-catalyzed synthesis of biologically active (S)-nilvadipine, Heterocycles 35, 603-606.
25. Ebiike, H., Terao, Y. and Achiwa, K. (1991) Acyloxymethyl as activating group in lipase-catalyzed enantioselective hydrolysis. A versatile approach to chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates, Tetrahedron Lett. 32, 5805-5808.
26. Ebiike, H., Yamazaki, Y. and Achiwa, K. (1995) Lipase-catalyzed enantiosynthesis of (R)- and (S -2-(benzyl(phenyl)amino)ethyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2, 6-dimethyl-4-(3-nitrophenyl)-3-pyridine-carboxylate (NZ 105), Chem. Pharm. Bull. 43, 1251-1253.
27. Eisner, U. and Kuthan, J. (1972) Chemistry of dihydropyridines, Chem. Rev. 72, 1-42.
28. Emanuel', N.M., Obukhova, L.K., Dubur, G.J., Tirzit, G.D. and Uldrikis, J.R. (1985) Geroprotective activity of 2,6-dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridine, Dokl. Akad. Nauk SSSR 284, 1271-1274.
29. Enders, D., Muller, S. and Demir, A.S. (1988) Enantioselective Hantzsch dihydropyridine synthesis via metalated chiral alkyl acetoacetate hydrazones, Tetrahedron Lett. 29, 6437-6440.
30. Faber, K. (1997) Biotransformations in organic chemistry (Springer-Verlag, Berlin, Heidelberg).
31. Franckowiak, J., Boshagen, H., Bossert, F., Goldmann, S., Meyer, H., Wehinger, E., Stoltefuss, J., Schramm, M., Thomas, J. and Towart, R. (1983) Dihydropyridines; having positively inotropic action, novel compounds, their use in medicaments and processes for their preparation. DE 3206671; Chem. Abstr. 98, 198038 (1983).
32. Genain, G. (1988) Resolution of 1,4-dihydropyridine derivatives. EP 0273349; espγenet database: http://www.espacenet.com
33. Germane, S., Misane, I. and Klusa, V. (1995) Alcohol-induced accelerated aging in mice: A convenient model for testing the normalizing influence of cerebrocrast on the altered CNS functioning, Laboratornye Zhyvotnye 5, 73-81.
34. Goldmann, S. and Stoltefuss, J. (1991) 1,4-Dihydropyridines: Effects of chirality and conformation on the calcium antagonist and calcium agonist activities, Angew. Chem., Int. Ed. Engl. 30, 1559-1578.
35. Goldmann, S., Stoltefuss, J. and Born, L. (1992) Determination of the absolute configuration of the active amlodipine enantiomer as ( - )-S: A correction, J. Med. Chem. 35, 3341-3344.
36. Gorlitzer, K., Kramer, C. and Boyle, C. (2000) Synthesis and transformations of ethyl 1,4-dihydro-4-oxo(1)benzofuro (3,2-b)pyridine-3-carboxylic acid esters: new antibacterial agents, Pharmazie 55, 651-658.
37. Hantzsch, A. (1881) Condensationsprodukte aus Aldehydammoniak und ketonartigen Verbindungen, Ber. 14, 1637-1638.
38. Hantzsch, A. (1882) Über die Synthese pyridinartige Verbindungen aus Acetessigäther und Aldehydammoniak, Justus Liebigs Ann. Chem. 215, 1-82.
39. Hillier, M.C. and Reider, P.J. (2002) Stereoselective synthesis from a process research perspective, Drug Discov. Today 7, 303-314.
40. Hirose, Y., Kariya, K., Sasaki, I., Kurono, Y. and Achiwa, K. (1993a) Carbamoylmethyl group as an activated group in protease- and base-catalyzed transesterification of 1,4-dihydropyridines: a novel asymmetric synthesis of valnidipine, Tetrahedron Lett. 34, 5915-5918.
41. Hirose, Y., Kariya, K., Sasaki, I., Kurono, Y. and Achiwa, K. (1993b) Protease-catalyzed enantioselective synthesis of optically active 1,4-dihydropyridines, Tetrahedron Lett. 34, 3441-3444.
42. Hirose, Y., Kariya, K., Sasaki, I., Kurono, Y., Ebiike, H. and Achiwa, K. (1992) Drastic solvent effect on lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines, Tetrahedron Lett. 33, 7157-7160.
43. Holdgrun, X.K. and Sih, C.J. (1991) A chemoenzymatic synthesis of optically-active dihydropyridines, Tetrahedron Lett. 32, 3465-3468.
44. Hyvonen, Z., Plotniece, A., Reine, I., Chekavichus, B., Duburs, G. and Urtti, A. (2000) Novel cationic amphiphilic 1,4-dihydropyridine derivatives for DNA delivery, Biochim. Biophys. Acta 1509, 451-466.
45. Hyvonen, Z., Ruponen, M., Ronkko, S., Suhonen, P. and Urtti, A. (2002) Extracellular and intracellular factors influencing gene transfection mediated by 1,4-dihydropyridine amphiphiles, Eur. J. Pharm. Sci. 15, 449-460.
46. Inotsume, N. and Nakano, M. (2002) Stereoselective determination and pharmacokinetics of dihydropyridines: an updated review, J. Biochem. Biophys. Methods 54, 255-274.
47. Inouye, M., Mio, T. and Sumino, K. (2000) Nilvadipine protects low-density lipoprotein cholesterol from in vivo oxidation in hypertensive patients with risk factors for atherosclerosis, Eur. J. Clin. Pharmacol. 56, 35-41.
48. Iqbal, N., Vo, D., McEwen, C.A., Wolowyk, M.W. and Knaus, E.E. (1994) Enantioselective syntheses and calcium channel modulating effects of ( + )- and ( - )-3-isopropyl 5-(4-methylphenethyl) 1,4-dihydro-2,6-dimethyl-4-(2-pyridyl)-3,5-pyridinedicarboxylates, Chirality 6, 515-520.
49. Ivanov, E.V., Ponomarjeva, T.V., Merkusev, G.N., Dubur, G.J., Bisenieks, E.A., Dauvarte, A.Z. and Pilscik, E.M. (1990) A new skin radioprotective agent Diethon (experimental study), Radiobiol. Radiother. 31, 69-78.
50. Klegeris, A., Liutkevicius, E., Mikalauskiene, G., Duburs, G., McGeer, P.L. and Klusa, V. (2002) Anti-inflammatory effects of cerebrocrast in a model of rat raw edema and mononuclear THP-1 cells, Eur. J. Pharmacol. 441, 203-208.
51. Klusa, V. (1995) Cerebrocrast: Neuroprotectant, cognition enhancer, Drugs of the Future 20, 135-138.
52. Klusa, V. and Duburs, G. (1996) Cognition enhancers (Nootropic drugs), Acta Medica Baltica 3, 104-114.
53. Klusa, V. and Germane, S. (1996) Alcoholized maternal rat offspring: a model for testing the physical and psychoemotional neurodeficit, Scand. J. Lab. Anim. Sci. 23, 403-409.
54. Kobayashi, T., Inoue, T., Nishino, S., Fujihara, Y., Oizumi, K. and Kimura, T. (1995) Novel 2-amino-1,4-dihydropyridine calcium antagonists. II. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having N,N dialkylaminoalkoxycarbonyl groups at 3- and/or 5-position, Chem. Pharm. Bull. 43, 797-817.
55. Kongsamut, S., Kamp, T.J., Miller, R.J. and Sanguinetti, M.C. (1985) Calcium channel agonist and antagonist effects of the stereomers of the dihydropyridine 202-791, Biochem. Biophys. Res. Commun. 130, 141-148.
56. Kozlov, E.I., Ivanova, R.A., Dubur, G.J. and Uldrikis, J.R. (1978) Dihydropyridine derivatives - new effective stabilizers of vitamin A oil solutions, Khim.-Farm. Zh. 12, 101-105.
57. Kumsar, K.K., Velena, A.H., Dubur, G.J., Uldrikis, J.P. and Zidermane, A.A. (1971) Effect of 1,4-dihydropyridine and 1,6-dihydropyrimidine derivatives on energy metabolism of normal and tumor cells, Biokhimiia 36, 1204-1208.
58. Kuthan, J. and Kurfurst, A. (1982) Development in dihydropyridine chemistry Ind. Eng. Chem. Prod. Res. Dev. 21, 191-261.
59. Kuzhir, T.D., Dalivelia, O.V and Savina, N.V. (1999) Modification of the repair processes in chemical mutagenesis in Drosophila melanogaster, Genetika 35, 919-924.
60. Lamm, B., Simonsson, R. and Sundell, S. (1989) Synthesis of enantiomers of fellodipine and determination of their absolute configuration, Tetrahedron Lett. 30, 6423-6426.
61. Loev, B. and Goodman, M.M. (1975) "Hantzsch-type" dihydropyridines. IV(1). Carboxylic acids, J. Heterocycl. Chem. 12, 363-365.
62. Mantle, D., Patel, V.B., Why, H.J., Ahmed, S., Rahman, I., MacNee, W., Wassif, W.S., Richardson, P.J. and Preedy, V.R. (2000) Effects of lisinopril and amlodipine on antioxidant status in experimental hypertension, Clin. Chim. Acta 299, 1-10.
63. Marchalin, S., Chudik, M., Mastihuba, V. and Decroix, B. (1998) Use of enzymes in preparation of enantiopure 1,4-dihydropyridines, Heterocycles 48, 1943-1957.
64. 2-1, 4-dihydropyridines: evidence for two cyclic GMP-dependent effector pathways, Br. J. Pharmacol. 116, 3293-3301.
65. Misane, I., Klusa, V., Dambrova, M., Germane, S., Duburs, G., Bisenieks, E., Rimondini, R. and Ogren, S.O. (1998) "Atypical" neuromodulatory profile of glutapyrone, a representative of a novel 'class' of amino acid containing dipeptide-mimicking 1,4-dihydropyridine (DHP) compounds: In vitro and in vivo studies, Eur. Neuropsychopharmacol. 8, 329-347.
66. Miyashita, K., Nishimoto, M., Ishino, T., Obika, S. and Imanishi, T. (1995) Novel and chiral Hantzsch-type 1,4-dihydropyridines having a p-tolylsulfinyl group. Synthesis and biological activities as calcium channel antagonists, Chem. Pharm. Bull. 43, 711-713.
67. Morgan, B., Zaks, A., Dodds, D.R., Liu, J., Jain, R., Megati, S., Njoroge, F.G. and Girijavallabhan, V.M. (2000) Enzymatic kinetic resolution of piperidine atropisomers: Synthesis of a key intermediate of the farnesyl protein transferase inhibitor, SCH66336, J. Org. Chem. 65, 5452-5459.
68. Natale, N.R. (2000) Learning from the Hantzsch synthesis, Chemical Innovation 30, 22-28.
69. Ogawa, T., Hatayama, K., Maeda, H. and Kita, Y. (1994) Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Syntheis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates, Chem. Pharm. Bull. 42, 1579-1589.
70. Ogawa, T., Matsumoto, K., Yokoo, C., Hatayama, K. and Kitamura, K. (1993) Synthesis and configurational assignment of methyl 3-nitrooxypropyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3, 5-carboxylate. J. Chem. Soc. Perkin Trans. 1 525-528.
71. Reeve, C.D., Crout, D.H.G., Cooper, K. and Fray, M.J. (1992) An optically pure 1,4-dihydropyridine from a resolution catalysed rabbit liver esterase, Tetrahedron: Asymmetry 3, 785-794.
72. Robertson, R.M. and Robertson, D. (1996) Drugs used for the treatment of myocardial ischemia, In: Hardman, J.G., Limbird, L.E., Molinoff, P.B., Ruddon, R.W. and Goodman Gilman, A., eds, Goodman and Gilman's: The pharmacological basis of therapeutics (McGraw-Hill Companies, Inc), pp. 759-779.
73. Rubene, D.J., Tirzit, G.D. and Dubur, G.J. (1982) Interaction of some derivatives of 1,4-dihydropyridine with Fenton's reagent. Latvijas PSR ZA vestis, Chem. ser. 212-215.
74. Salazar, L. and Sih, C.J. (1995) Optically-active dihydropyridines via lipase-catalyzed enantioselective hydrolysis, Tetrahedron: Asymmetry 6, 2917-2920.
75. Sausins, A. and Duburs, G. (1988) Synthesis of 1,4-dihydropyridines by cyclocondensation reactions, Heterocycles 27, 269-289.
76. Sausins, A. and Duburs, G. (1992) Synthesis of 1,4-dihydropyridines in cyclocondensation reactions. Khim. Geterotsikl. Soed. 435-467.
77. Sausins, A. and Duburs, G. (1993) Reactions of 1,4-dihydropyridines. Khim. Geterotsikl. Soed. 579-612.
78. Shah, A., Gaveriya, H., Motohashi, N., Kawase, M., Saito, S., Sakagami, H., Satoh, K., Tada, Y., Solymosi, A., Walfard, K. and Molnar, J. (2000) 3,5-Diacetyl-1,4-dihydropyridines: synthesis and MDR reversal in tumor cells, Anticancer Res. 20, 373-377.
79. Shan, R., Howlett, S.E. and Knaus, E.E. (2002) Syntheses, calcium channel agonist-antagonist modulation activities, nitric oxide release, and voltage-clamp studies of 2-nitrooxyethyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2-trifluoromethylphenyl) pyridine-5-carboxylate enantiomers, J. Med. Chem. 45, 955-961.
80. Shibanuma, T., lwanani, M., Okuda, K., Takenaka, T. and Murakami, M. (1980) Synthesis of optically active 2-(N-benzyl-N methylamino)ethyl methyl-2,6-dimethyl-4-(m nitrophenyl -1,4-dihydropyridine-3,5-dicarboxylate (Nicardipine), Chem. Pharm. Bull. 28, 2809-2812.
81. Sih, C.J., Gu, S.Q., Holdgrun, X. and Harris, K. (1992) Optically-active compounds via biocatalytic methods, Chirality 4, 91-97.
82. Sobolev, A., Franssen, M.C.R., Makarova, N., Duburs, G. and de Groot, A. (2000) C. antarctica lipase catalyzed hydrolysis of 4-substituted bis(ethoxycarbonylmethyl) 1,4-dihydropyridine-3,5-dicarboxylates as the key step in the synthesis of optically active dihydropyridines, Tetrahedron: Asymmetry 11, 4559-4569.
83. Sobolev, A., Franssen, M.C.R., Poikans, J., Duburs, G. and de Groot, A. (2002a) Enantioselective lipase-catalysed kinetic resolution of acyloxymethyl and ethoxycarbonylmethyl esters of 1,4-dihydroisonicotinic acid derivatives, Tetrahedron: Asymmetry 13, 2389-2397.
84. Sobolev, A., Franssen, M.C.R., Vigante, B., Cekavicus, B., Makarova, N., Duburs, G. and de Groot, A. (2001) An efficient chemoenzymatic approach to enantiomerically pure 4-[2-(difluoromethoxy)phenyl] substituted 1,4-dihydropyridine 3,5-dicarboxylates, Tetrahedron: Asymmetry 12, 3251-3256.
85. Sobolev, A., Franssen, M.C.R., Vigante, B., Cekavicus, B., Zhalubovskis, R., Kooijman, H., Spek, A.L., Duburs, G. and de Groot, A. (2002b) The effect of acyl chain length and branching on the enantioselectivity of C. rugosa lipase in the kinetic resolution of 4-(2-difluoromethoxyphenyl) substituted 1,4-dihydropyridine 3,5-diesters, J. Org. Chem. 67, 401-410.
86. Soons, P.A., Roosemalen, M.C.M. and Breimer, D.D. (1990) Enantioselective determination of felodipine and other chiral dihydropyridine calcium entry blockers in human plasma, J. Chromatogr. 528, 343-356.
87. Stout, D.M. and Meyers, A.I. (1982) Recent advances in the chemistry of dihydropyridines, Chem. Rev. 82, 223-243.
88. Strong, M. (1999) FDA policy and regulation of stereoisomers: paradigm shift and the future of safer, more effective drugs, Food Drug Law J. 54, 463-487.
89. Suh, J.J. and Hong, Y.H. (1989a) Synthesis of 1,4-dihydropyridine carboxylic acids, Yakhak Hoechi 33, 80-86.
90. Suh, J.J. and Hong, Y.H. (1989b) Synthesis of 1,4-dihydropyridine carboxylic acids (II), Yakhak Hoechi 33, 219-225.
91. Tarasenko, L.M., Neporada, K.S. and Klusha, V. (2002) Stress-protective effect of glutapyrone belonging to a new type of amino acid-containing 1,4-DHPs on peridontal tissues and stomach in rats with different resistance to stress, Bull. Exp. Biol. Med. 133, 369-371.
92. Tirzitis, G., Kirule, I. and Duburs, G. (1988) Antioxidationsaktivitaet der 3,5-Dicarbonylderivate des 2,6-Dimethyl-1,4-Dihydropyridins, Fat. Sci. Technol. 90, 411-413.
93. Tokuma, Y. and Noguchi, H. (1995) Stereoselective pharmacokinetics of dihydropyridine calcium antagonists, J. Chromatogr. A. 694, 181-193.
94. Triggle, D.J. (2003) 1,4-Dihydropyridines as calcium channel ligands and privileged structures, Cell. Mol. Neurobiol. 23, 293-303.
95. Uldrikis, Y.R., Preisa, I.E., Dubur, G.Y., Zidermane, A.A., Biseniex, E.A. and Tirzit, G.D. (1980) 2,6-Dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid esters and method for preparing same. US 4293700; Chem. Abstr. 93, 168135 (1980).
96. Uno, T., Ohkubo, T. and Sugawara, K. (1997) Enantioselective high-performance liquid chromatographic determination of nicardipine in human plasma, J. Chromatogr. B 698, 181-186.
97. van Zwieten, P.A. (1998) Pharmacological profile of barnidipine: a single optical isomer dihydropyridine calcium antagonist, Blood Press. Suppl. 1, 5-8.
98. Velena, A., Zilbers, J. and Duburs, G. (1999) Derivatives of 1,4-dihydropyridines as modulators of ascorbate-induced lipid peroxidation and high-amplitude swelling of mitochondria, caused by ascorbate, sodium linoleate and sodium pyrophosphate, Cell Biochem. Funct. 17, 237-252.
99. Vo, D., Matowe, W.C., Ramesh, M., Iqbal, N., Wolowyk, M.W., Howlett, S.E. and Knaus, E.E. (1995) Syntheses, calcium channel agonist-antagonist modulation activities, and voltage-clamp studies of isopropyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-pyridinylpyridine-5-carboxylate racemates and enantiomers, J. Med. Chem. 38, 2851-2859.
100. Vogel, A. (1983) 1,4-Dihydropyridine derivatives, preparation thereof and pharmaceutical compositions containing them. DE 3320616; Chem. Abstr. 101, 7162s (1984).
101. Watson, W.P. and Little, H.J. (1999) Correlation between increases in dihydropyridine binding in vivo and behavioural signs of ethanol withdrawal in mice, Alcohol Alcohol. 34, 35-42.
102. Yamazaki, Y. and Achiwa, K. (1996) Lipase AH-catalyzed asymmetric synthesis of (S)-( - )-NB 818, Heterocycles 42, 169-171.
103. Yamazaki, Y., Ebiike, H. and Achiwa, K. (1994) Determination of the absolute configuration of biologically active (S)-( - )-NB 818 and its structural correlation with the stereoselectivity of the channel blocking action, Chem. Pharm. Bull. 42, 1968-1970.
104. Yao, K., Ina, Y., Nagashima, K., Ohmori, K. and Ohno, T. (2000) Antioxidant effects of calcium antagonists in rat brain homogenates, Biol. Pharm. Bull. 23, 766-769.