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Synthesis, QSAR and Calcium Channel Antagonist Activity of New 1,4‐Dihydropyridine Derivatives Containing 1‐Methyl‐4,5‐dichloroimidazolyl Substituents
Author(s) -
Hosseini Maryam,
Miri Ramin,
Amini Mohsen,
Mirkhani Hossein,
Hemmateenejad Bahram,
Ghodsi Shahram,
Alipour Eskandar,
Shafiee Abbas
Publication year - 2007
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200600211
Subject(s) - chemistry , calcium channel , antagonist , stereochemistry , substituent , dihydropyridine , quantitative structure–activity relationship , nifedipine , calcium , lipophilicity , biochemistry , receptor , organic chemistry
A group of dialkyl and diarylester analogues of nifedipine, in which the ortho ‐nitrophenyl group at position 4 was replaced by a 1‐methyl‐4,5‐dichloroimidazolyl substituent, were synthesized and evaluated as calcium‐channel antagonists using the high K + concentration of guinea‐pig ileum longitudinal smooth muscle. The structure of all compounds was confirmed by IR, 1 H‐NMR, and mass spectra. The calcium‐channel antagonist activity of compounds 10a–f demonstrated that compound 10b was the most active and 10f the least active one. With unsymmetrical diesters 12a–k , the most active compound was the ethyl, phenethyl derivative. Structural parameters on the calcium‐channel antagonist activity were evaluated by QSAR analysis and a linear correlation was found between the –log IC 50 values of these compounds and their constitutional and topological properties.