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2‐Aryl‐substituted, benzo‐anellated 5‐membered heterocyclic compounds as potentially active substances for the cardiovascular system: 1,3‐Benzothiazolyl‐ and 1,3‐benzoxazolylbenzylphosphonates
Author(s) -
Rose Ulrich
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290245
Subject(s) - chemistry , benzothiazole , aryl , phosphonate , stereochemistry , ring (chemistry) , inotrope , halogenation , medicinal chemistry , organic chemistry , medicine , alkyl
In the course of investigations on structure‐activity relationships of calcium antagonists analogous to fostedil, a series of 2‐aryl‐ and 2‐arylvinyl‐substituted 1,3‐henzothiazoles and 1,3‐benzoxazoles bearing a phosphonate group on the phenyl ring has been synthesized by cyclization, bromination, and subsequent Michaelis‐Arbuzow reaction. Pharmacological investigations on isolated organs from guinea pigs revealed both negative inotropic effects and a relaxing action on smooth musculature; these activities were particularly pronounced in the 1,3‐benzothiazole compound group.