acsomega.1c05222.pdf (1.29 MB)
Download file

(Benzylideneamino)triazole-thione derivatives of flurbiprofen: an efficient microwave-assisted synthesis and in vivo analgesic potential

Download (1.29 MB)
journal contribution
posted on 25.01.2022, 12:27 authored by Muhammad Zaheer, Muhammad Zia-ur-Rehman, Rubina Munir, Nadia Jamil, Saiqa Ishtiaq, Rahman Shah Zaib Saleem, Mark ElsegoodMark Elsegood
Triazole is an imperative heterocycle renowned for its broad-spectrum biological significance. In this manuscript, facile microwave-assisted synthesis of a series of 4-(benzylideneamino)-3-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1H-1,2,4-triazole-5(4H)-thione 6(a-m) derivatives along with their in vivo analgesic activity is reported. 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)propanoic acid (flurbiprofen) was converted to methyl 2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanoate using microwave irradiation, followed by its hydrazinolysis with hydrazine monohydrate. 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)propanehydrazide thus obtained was converted to 4-amino-3-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1H-1,2,4-triazole-5(4H)-thione, followed by its condensation with different aromatic aldehydes to get the title compounds. Structures of all the synthesized compounds were established using different methods (1H NMR and 13C NMR spectroscopies, mass spectrometry, and elemental analysis) and evaluated for their potential as analgesic agents by tail flick, hot plate, and writhing methods. The results of this in vivo study revealed several compounds as potent analgesic agents among which compound 6e showed significant analgesic effect for all the three assays employed.

History

School

  • Science

Department

  • Chemistry

Published in

ACS Omega

Volume

6

Issue

46

Pages

31348 - 31357

Publisher

American Chemical Society

Version

VoR (Version of Record)

Rights holder

© The Authors

Publisher statement

This is an Open Access Article. It is published by the American Chemical Society under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International Licence (CC BY-NC-ND 4.0). Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Acceptance date

28/10/2021

Publication date

2021-11-12

Copyright date

2021

eISSN

2470-1343

Language

en

Depositor

Dr Mark Elsegood. Deposit date: 25 January 2022