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

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

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, 14176, Iran
2. Pharmacology and Toxicology Department, Pharmaceutical Sciences Branch and Pharmaceutical Sciences Research Center, Islamic Azad University, Tehran, Iran
3. School of Chemistry, College of Science, University of Tehran, Tehran, Iran

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.

2. 5-[Aryloxypyridyl (Or Nitrophenyl)]-4H-1,2,4-Triazoles As Novel Flexible Benzodiazepine Analogues: Synthesis, Receptor Binding Affinity and Lipophilicity-Dependent Anti-Seizure Onset of Action, Bioorganic Chemistry (2021)

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Style	Citing Format
MLA	Nakhostin A, et al.. "Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides." Medicinal Chemistry Research, vol. 25, no. 10, 2016, pp. 2220-2236.
APA	Nakhostin A, Mirseyyedhosein S, Toolabi M, Khodabakhsh P, Aghamiri H, Ghaffari S, Shafaroodi H, Shayesteh A, Amini M, Shafiee A, Navidpour L (2016). Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides. Medicinal Chemistry Research, 25(10), 2220-2236.
Chicago	Nakhostin A, Mirseyyedhosein S, Toolabi M, Khodabakhsh P, Aghamiri H, Ghaffari S, Shafaroodi H, et al.. "Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides." Medicinal Chemistry Research 25, no. 10 (2016): 2220-2236.
Harvard	Nakhostin A et al. (2016) 'Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides', Medicinal Chemistry Research, 25(10), pp. 2220-2236.
Vancouver	Nakhostin A, Mirseyyedhosein S, Toolabi M, Khodabakhsh P, Aghamiri H, Ghaffari S, et al.. Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides. Medicinal Chemistry Research. 2016;25(10):2220-2236.
BibTex	@article{ author = {Nakhostin A and Mirseyyedhosein S and Toolabi M and Khodabakhsh P and Aghamiri H and Ghaffari S and Shafaroodi H and Shayesteh A and Amini M and Shafiee A and Navidpour L}, title = {Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides}, journal = {Medicinal Chemistry Research}, volume = {25}, number = {10}, pages = {2220-2236}, year = {2016} }
RIS	TY - JOUR AU - Nakhostin A AU - Mirseyyedhosein S AU - Toolabi M AU - Khodabakhsh P AU - Aghamiri H AU - Ghaffari S AU - Shafaroodi H AU - Shayesteh A AU - Amini M AU - Shafiee A AU - Navidpour L TI - Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides JO - Medicinal Chemistry Research VL - 25 IS - 10 SP - 2220 EP - 2236 PY - 2016 ER -

Style

Citing Format

MLA

Nakhostin A, et al.. "Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides." Medicinal Chemistry Research, vol. 25, no. 10, 2016, pp. 2220-2236.

APA

Nakhostin A, Mirseyyedhosein S, Toolabi M, Khodabakhsh P, Aghamiri H, Ghaffari S, Shafaroodi H, Shayesteh A, Amini M, Shafiee A, Navidpour L (2016). Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides. Medicinal Chemistry Research, 25(10), 2220-2236.

Chicago

Nakhostin A, Mirseyyedhosein S, Toolabi M, Khodabakhsh P, Aghamiri H, Ghaffari S, Shafaroodi H, et al.. "Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides." Medicinal Chemistry Research 25, no. 10 (2016): 2220-2236.

Harvard

Nakhostin A et al. (2016) 'Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides', Medicinal Chemistry Research, 25(10), pp. 2220-2236.

Vancouver

Nakhostin A, Mirseyyedhosein S, Toolabi M, Khodabakhsh P, Aghamiri H, Ghaffari S, et al.. Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides. Medicinal Chemistry Research. 2016;25(10):2220-2236.

BibTex

@article{ author = {Nakhostin A and Mirseyyedhosein S and Toolabi M and Khodabakhsh P and Aghamiri H and Ghaffari S and Shafaroodi H and Shayesteh A and Amini M and Shafiee A and Navidpour L}, title = {Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides}, journal = {Medicinal Chemistry Research}, volume = {25}, number = {10}, pages = {2220-2236}, year = {2016} }

RIS

TY - JOUR
AU - Nakhostin A
AU - Mirseyyedhosein S
AU - Toolabi M
AU - Khodabakhsh P
AU - Aghamiri H
AU - Ghaffari S
AU - Shafaroodi H
AU - Shayesteh A
AU - Amini M
AU - Shafiee A
AU - Navidpour L
TI - Synthesis, Conformational Assignment, and Anti-Inflammatory Activities of N-Arylidene-2-(4-Chloro-2-(2-Substituted Phenoxy)Phenyl)Acetic Acid Hydrazides
JO - Medicinal Chemistry Research
VL - 25
IS - 10
SP - 2220
EP - 2236
PY - 2016
ER -

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