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Design, Synthesis, and Calcium Channel Antagonist Activity of New 1,4‐Dihydropyridines Containing 4‐(5)‐Chloro‐2‐ethyl‐5‐(4)‐imidazolyl Substituent
Author(s) -
Davood Asghar,
Mansouri Niloufar,
Rerza Dehpour Ahmad,
Shafaroudi Hamed,
Alipour Eskandar,
Shafiee Abbas
Publication year - 2006
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.200600013
Subject(s) - chemistry , substituent , nifedipine , calcium channel , stereochemistry , antagonist , chemical synthesis , calcium , organic chemistry , in vitro , receptor , biochemistry
A series of dialkyl, dicycloalkyl, and diaryl ester analogues of nifedipine, in which the ortho ‐nitro phenyl group at position 4 is replaced by the 4‐(5)‐chloro‐2‐ethyl‐5‐(4)‐imidazolyl substituent, were synthesized and evaluated as calcium channel antagonists using the high K + contraction of guinea pig ileal longitudinal smooth muscle. The results for the symmetrical ester series showed that increasing the length of the chain in C 3 ‐ and C 5 ‐ester substituents increased the activity and the most active compound was the diphenylethyl ester derivative, so it was more active than the reference drug nifedipine. In unsymmetrical diester series, when R 1 is methyl or ethyl, increasing lipophilic properties in the R substituent, increased the activity. The most active compounds were methyl/phenethyl and ethyl/phenethyl ester derivatives, being slightly more active than nifedipine.