Synthesis and antihypertensive activity evaluation in spontaneously hypertensive rats of nitrendipine analogues

Medicinal Chemistry Research

Volumn 20, Issue 8, 2011, Pages 1325-1330

  Zhou, Kai ^a   Wang, Xiao Meng ^a   Zhao, Yi Zhi ^a   Cao, Yong Xiao ^a   Fu, Qiang ^a   Zhang, San Qi ^a  

^a MEDICAL SCHOOL OF XI AN JIAOTONG UNIVERSITY   (China)

Author keywords

1,4 Dihydropyridines; Antihypertensive activity; Enantiomer; Nitrendipine analogues; SHR

Indexed keywords

3 METHYL 5 OCTYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; 3 METHYL 5 OCTYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; 3 METHYL 5 PENTYL 2,6 DIMETHYL 4\ (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; 3 METHYL 5 PROPYL 2,6 DIMETHYL 4\ (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; 5 DECYL 3 METHYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; 5 DODECYL 3 METHYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; 5 ETHYL 3 METHYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4DIHYDROPYRIDINE 3,5 DICARBOXYLATE; 5 HEPTYL 3 METHYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; DIMETHYL 2,6 DIMETHYL 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; NITRENDIPINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; HYPERTENSION; MALE; NONHUMAN; RAT; SPONTANEOUSLY HYPERTENSIVE RAT;

EID: 80054726645     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9477-0     Document Type: Article

References (19)

1. Ashimori A, Uchida T, Ohtaki Y, Tanaka M, Ohe K, Fukaya C, Watanabe M, Kagitani M, 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-pyridine-dicarboxylate hydrochloride. Chem Pharm Bull 39:108-111
2. Baindur N, Rutledge A, Triggle DJ (1993) A homologous series of permanently charged 1,4-dihydropyridines: Novel probes designed to localize drug binding sites on ion channels. J Med Chem 36:3743-3746
3. Fu Q, Sanbe H, Kgawa C, Kunimoto KK, Haginaka J (2003) Uniformly sized molecularly imprinted polymer for (S)-nilvadipine. Comparison of chiral recognition ability with HPLC chiral stationary phases based on a protein. Anal Chem 75:191-198 (Pubitemid 36119764)
4. Ghorbani-Choghamarani A, Zolfigol MA, Salehi P, Ghaemi E, Madrakian E, Nasr-Isfahani H, Shahamirian M (2008) An efficient procedure for the synthesis of Hantzsch 1,4-dihydropyridines under mild conditions. Acta Chim Slov 55:644-647
5. Levine CB, Fahrbach KR, Frame D, Connelly JE, Estok RP, Stone LR, Ludensky V (2003) Effect of amlodipine on systolic blood pressure. Clin Ther 25:35-57 (Pubitemid 36206737)
6. Liu F, Qiu M, Zhai SD (2010) Tolerability and effectiveness of (S)- amlodipine compared with racemic amlodipine in hypertension: A systematic review and meta-analysis. Curr Ther Res 71:1-29
7. Motomura S, Wu ZJ, Hashimoto K (1993) Lacidipine, a new longacting dihydropyridine calcium antagonist, has high vascular selectivity against all intracardiac variables. Heart Vessels 8: 16-22 (Pubitemid 23099161)
8. Palacios F, Herran E, Rubiales G, Alonso C (2007) Regioselective synthesis of pyridines and dihydropyridines derived from b-amino acids and amino phosphonates by reaction of N-vinylic phosphazenes with a,b-unsaturated ketones. Tetrahedron 63: 5669-5676 (Pubitemid 46755336)
9. Park JY, Kim KA, Park PW, Lee OJ, Ryu JH, Lee GH, Ha MC, Kim JS, Kang SW, Lee KR (2006) Pharmacokinetic and pharmacodynamic characteristics of a new S-amlodipine formulation in healthy Korean male subjects: A randomized, open-label, twoperiod, comparative, crossover study. Clin Ther 28:1837-1847
10. Peri R, Padmanabhan S, Rutledge A, Singh S, Triggle DJ (2000) Permanently charged chiral 1,4-Dihydropyridines: Molecular probes of L-type calcium channels. synthesis and pharmacological characterization of methyl (x-trimethylalkylammonium) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5- pyridinedicarboxylate iodide, calcium channel antagonists. J Med Chem 43: 2906-2914 (Pubitemid 30599648)
11. Raju P, Ravindra V, Mathad VT, Dubey PK, Reddy PP (2009) A facile, one-pot synthesis of lacidipine using in situ generation of wittig intermediates. Org Process Res Dev 13:710-715
12. Sabitha G, Reddy GSKK, Reddy CS, Yadav JS (2003) A novel TMSImediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature. Tetrahedron Lett 44:4129-4131 (Pubitemid 36549145)
13. Shibanuma T, Iwanami M, Okuda K, Takenaka T, 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 (Pubitemid 11208752)
14. Tokuma YJ, Noguchi H (1995) Stereoselective pharmacokinetics of dihydropyridine calcium antagonists. J Chromatogr A 694: 181-193
15. Trachtman H, Mahan RFJD, Portman R, Matoo IRTK, Tou C, Klibaner M (2003) Clinical trial of extended-release felodipine in pediatric essential hypertension. Pediatr Nephrol 18:548-553 (Pubitemid 36790096)
16. Wehinger E, Meyer H, Knorr A (1983) Neue verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel. EP 0088276A1
17. Wu XY, Hu AX, Tan Y (2003) Synthesis improvement of calcium antagonist pranidipine. Chin J Appl Chem 20:1015-1017
18. Zhang BL, He W, Shi Xin, Huan ML, Huang QJ, Zhou SY (2010) 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. Bioorg Med Chem Lett 20: 805-808
19. Zolfigol MA, Salehi P, Safaiee M (2006) An efficient and eco-friendly procedure for the synthesis of Hantzsch ethyl 1,4-dihydro-2,6- dimethylpyridine-3,5-dicarboxylates under mild and green conditions. Lett Org Chem 3:153-156