Synthesis, conformational assignment, and anti-inflammatory activities of N-arylidene-2-(4-chloro-2-(2-substituted phenoxy)phenyl)acetic acid hydrazides

doi:10.1007/s00044-016-1656-1

Paper

Synthesis, conformational assignment, and anti-inflammatory activities of N-arylidene-2-(4-chloro-2-(2-substituted phenoxy)phenyl)acetic acid hydrazides

Published Jul 28, 2016 · Afraz Nakhostin, Samaneh Mirseyyedhosein, Mahsa Toolabi

Medicinal Chemistry Research

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3

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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 ste-reoisomers 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,

In Vitro Study

Study Snapshot

N-arylidene-2-(4-chloro-2-(2-fluoro or chlorophenoxy)phenyl)acetic acid hydrazides show moderate to excellent anti-inflammatory activity in carrageenan-induced rat paw edema assays.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis, conformational assignment, and anti-inflammatory activities of N-arylidene-2-(4-chloro-2-(2-substituted phenoxy)phenyl)acetic acid hydrazides

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