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Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides Publisher



Nakhostin A1 ; Mirseyyedhosein S2 ; Toolabi M1 ; Khodabakhsh P2 ; Aghamiri H2 ; Ghaffari S2 ; Shafaroodi H2 ; Shayesteh A3 ; Amini M1 ; Shafiee A1 ; Navidpour L1
Authors

Source: Medicinal Chemistry Research Published:2016


Abstract

A series of N-arylidene-2-(4-chloro-2-(2-fluoro or chlorophenoxy)phenyl)acetic acid hydrazides (16 or 17) was synthesized for their anti-inflammatory activity by the condensation of corresponding hydrazide and aromatic aldehydes. Characterization of these compounds by proton nuclear magnetic resonance showed most of the protons as two separate peaks. The energy was calculated for each possible configuration, and their stereochemical behavior was studied using proton nuclear magnetic resonance techniques. The results indicated that the most stable stereoisomers are the two E geometrical isomers, which undergo a rapid cis/trans amide equilibrium with the cis conformer predominating. These analogs exhibited moderate to excellent anti-inflammatory activity in carrageenan-induced rat paw edema assay. Among them, N-(3,4-dimethoxybenzylidene)-2-(4-chloro-2-(2-chlorophenoxy)phenyl)acetic acid hydrazide (17k) showed the highest anti-inflammatory activity relative to diclofenac sodium acid as a reference drug (86 % vs. 61 % reduction in inflammation post drug administration, respectively). © 2016, Springer Science+Business Media New York.
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