Synthesis and biological activity of the calcium modulator (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 805-808

  Zhang, Bang le ^a   He, Wei ^a   Shi, Xin ^a   Huan, Meng lei ^a   Huang, Qiu ju ^a   Zhou, Si yuan ^a  

^a FOURTH MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

1,4 Dihydropyridines; Calcium modulator; Receptor binding activity; Resolution

Indexed keywords

1,4 DIHYDRO 2,6 DIMETHYL 4 (3 NITROPHENYL) 3,5 PYRIDINEDICARBOXYLIC ACID METHYL PENTYL ESTER; 1,4 DIHYDROPYRIDINE RECEPTOR; 3 METHYL 5 PENTYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; CINCHONA ALKALOID; CINCHONIDINE; DICARBOXYLIC ACID DERIVATIVE; QUINIDINE; UNCLASSIFIED DRUG; 1,4-DIHYDROPYRIDINE; CALCIUM; CALCIUM CHANNEL L TYPE; DICARBOXYLIC ACID; DIHYDROPYRIDINE DERIVATIVE; PROTEIN BINDING;

ARTICLE; BINDING AFFINITY; BRAIN MEMBRANE; CRYSTALLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; HEART MUSCLE FIBER MEMBRANE; NONHUMAN; RAT; STEREOCHEMISTRY; ANIMAL; BRAIN CORTEX; COMPARATIVE STUDY; DRUG EFFECTS; HEART MUSCLE; METABOLISM; PHYSIOLOGY; STEREOISOMERISM; SYNTHESIS;

CINCHONA; RATTUS;

ANIMALS; CALCIUM; CALCIUM CHANNELS, L-TYPE; CEREBRAL CORTEX; DICARBOXYLIC ACIDS; DIHYDROPYRIDINES; MYOCARDIUM; PROTEIN BINDING; RATS; STEREOISOMERISM;

EID: 74049147493     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.104     Document Type: Article

References (31)

1. Safak C., and Simsek R. Mini. Rev. Med. Chem. 6 (2006) 747
2. Inotsume N., and Nakano M. J. Biochem. Biophys. Methods 54 (2002) 255
3. Kajino M., Wada Y., Nagai Y., Nagaoka A., and Meguro K. Chem. Pharm. Bull. 37 (1989) 2225
4. Cataldi M., Taglialatela M., Palagiano F., Secondo A., deCaprariis P., Amoroso S., diRenzo G., and Annunziato L. Eur. J. Pharmacol. 376 (1999) 169
5. Franckowiak G., Bechem M., Schramm M., and Thomas G. Eur. J. Pharmacol. 114 (1985) 223
6. Ashworth I., Hopes P., Levin D., Patel I., and Salloo R. Tetrahedron Lett. 43 (2002) 4931
7. Iqbal N., Vo D., McEwen C.A., Wolowyk M.W., and Knaus E.E. Chirality 6 (1994) 515
8. Martin N., Martinez-Grau A., Seoane C., Marco J.L., Albert A., and Cano F.H. Tetrahedron: Asymmetry 6 (1995) 877
9. Boatto G., Nieddu M., Faedda M.V., and deCaprariis P. Chirality 15 (2003) 494
10. Shibanuma T., Iwanami M., Okuda K., Takenaka T., and Murakami M. Chem. Pharm. Bull. 28 (1980) 2809
11. Ashimori A., Uchida T., Ohtaki Y., Tanaka M., Ohe K., Fukaya C., Watanabe M., Kagitani M., and Yokoyama K. Chem. Pharm. Bull. 39 (1991) 108
12. Peri R., Padmanabhan S., Rutledge A., Singh S., and Triggle D.J. J. Med. Chem. 43 (2000) 2906
13. Baranda A.B., Etxebarria N., Jiménez R.M., and Alonso R.M. J. Chromatogr. Sci. 43 (2005) 505
14. Tamazawa T., Arima H., Kojima T., Isomura Y., Okada M., Fujita S., Furuya T., Takenaka T., Inagaki O., and Terai M. J. Med. Chem. 29 (1986) 2504
15. Yang Z., Zhou S., Yang T., Mei Q., and Liu L. J. Fourth. Mil. Med. Univ. 25 (2004) 1794
16. Liu L., Mei Q., Zhang F., Chen L., and Zhao D. Chin. Pharmacol. Bull. 19 (2003) 796
17. Wang J., Guo W., Mei Q., Wang S., and Zhao D. J. Fourth. Mil. Med. Univ. 24 (2003) 1688
18. Wang L., Mei Q., Zhao D., Wu L., Tian Q., and Li J. Chin. Pharmacol. Bull. 16 (2000) 406
19. Liu L., Mei Q., and Zhao D. J. Fourth. Mil. Med. Univ. 22 (2001) 1456
20. Wang L., Mei Q., Zhao D., and Guo Z. Acta Pharmacol. Sin. 21 (2000) 623
21. Yao X., Gan H., Jia M., Fang Z., and Mei Q. J. Fourth. Mil. Med. Univ. 21 (2000) 311
22. Wang L., Mei Q., Zhao D., Tian Q., and Zhang Z. Chin. Pharm. J. 33 (1998) 282
23. Wang L., Pei Q., Mei Q., Zhao D., Li J., and Tian Q. Chin. Pharmacol. Bull. 13 (1997) 512
24. Bao C., Chen Z., and Yuan F. Chin. J. Pharm. 23 (1992) 8
25. Borghese A., Libert V., Zhang T., and Charles A.A. Org. Process Res. Dev. 8 (2004) 532
26. Wang Y., and Chen A.M. Org. Process Res. Dev. 12 (2008) 282
27. 1H NMR and IR spectra of (-)-(R)-3b were identical to those of another enantiomer (+)-(S)-3a.
28. 4 and evaporated in vacuo to give cinchonidine (93% yield) and quinidine (95% yield).
29. He W., Zhang B.-L., Jiang R., Liu P., Sun X.-L., and Zhang S.-Y. Tetrahedron Lett. 47 (2006) 5231
30. 1H NMR and IR spectra of (+)-(S)-1b were identical to those of another enantiomer (-)-(R)-1a.
31. (+)-(S)-1b = 33 min.