Studies on novel and chiral 1,4-dihydrpyridines. V. Hantzsch-type 1,4-dihydropyridines having a chiral sulfinyl group: Syntheses, structures, and biological activity as a calcium channel antagonist

Tetrahedron

Volumn 53, Issue 12, 1997, Pages 4279-4290

  Miyashita, Kazuyuki ^a   Nishimoto, Masahiro ^a   Ishino, Tetsuya ^a   Murafuji, Hidenobu ^a   Obika, Satoshi ^a   Muraoka, Osamu ^b   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; CALCIUM CHANNEL; CALCIUM CHANNEL BLOCKING AGENT; NIFEDIPINE;

ANIMAL TISSUE; ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; MESENTERIC ARTERY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RAT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; VASODILATATION; X RAY CRYSTALLOGRAPHY;

EID: 0031585043     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00155-5     Document Type: Article

References (38)

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35. 19. Owing to the steric repulsion between the benzene ring and the acetyl group of 4a and 4b, these two groups are not thought to conjugate with the double bond sufficiently. Consequently, this would make 4a and 4b less effective Michael acceptors than 4c.
36. 20. The mescenteric artery enucleated from a rat was perfused with a Tyrode solution containing KC1 (70 mM) and the high perfusion state was maintained. To the perfusion solution, a DMSO solution of the sample was added and the vasorelaxation was evaluated by measuring the perfusion pressure.
37. 1,9
38. 22. Although the conformation in the solution state is not clear, it would appear to be different from that in the crystalline state in some respects. However, it is obvious that this difference in conformation between the solution state and the crystalline state would not be a problem compared with the structural and stereochemical differences (i.e., 2Bb vs. 2Ba and 2Bb vs. 2Ab in Table 2).