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Synthesis, crystal structure and bioactivity of phenazine-1-carboxylic acylhydrazone derivatives

Wu, Shouting; Liang, Xi; Luo, Fang; Liu, Hua; Shen, Lingyi; Yang, Xianjiong; Huang, Yali; Xu, Hong; Wu, Ning; Zhang, Qilong; Redshaw, Carl

Authors

Shouting Wu

Xi Liang

Fang Luo

Hua Liu

Lingyi Shen

Xianjiong Yang

Yali Huang

Hong Xu

Ning Wu

Qilong Zhang

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry



Abstract

A phenazine-1-carboxylic acid intermediate was synthesized from the reaction of aniline and 2-bromo-3-nitro-benzoic acid. It was then esterified and reacted with hydrazine hydrate to afford phenazine-1-carboxylic hydrazine. Finally, 10 new hydrazone compounds 3a–3j were obtained by the condensation reaction of phenazine-1-carboxylic acid hydrazide and the respective aldehyde-containing compound. The structures were characterized by 1H and 13C NMR spectroscopy, MS and single crystal X-ray diffraction. The antitumor activity of the target compounds in vitro (HeLa and A549) was determined by thiazolyl blue tetrazolium bromide. The results showed that compound (E)-N′-(2-hydroxy-4-(2-(piperidine-1-yl) ethoxy) benzyl) phenazine-1-carbonyl hydrazide 3d exhibited good cytotoxic activity.

Citation

Wu, S., Liang, X., Luo, F., Liu, H., Shen, L., Yang, X., …Redshaw, C. (2021). Synthesis, crystal structure and bioactivity of phenazine-1-carboxylic acylhydrazone derivatives. Molecules, 26(17), https://doi.org/10.3390/molecules26175320

Journal Article Type Article
Acceptance Date Aug 27, 2021
Online Publication Date Sep 1, 2021
Publication Date Sep 1, 2021
Deposit Date Sep 1, 2021
Publicly Available Date Sep 2, 2021
Journal Molecules
Electronic ISSN 1420-3049
Publisher MDPI
Peer Reviewed Peer Reviewed
Volume 26
Issue 17
Article Number 5320
DOI https://doi.org/10.3390/molecules26175320
Keywords Phenazine-1-carboxylic acid; Acylhydrazone compounds; Crystal structure; Anticancer activity
Public URL https://hull-repository.worktribe.com/output/3830658

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Copyright Statement
Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses /by/4.0/)



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