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Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives

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...

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Autores principales: Wu, Shouting, Liang, Xi, Luo, Fang, Liu, Hua, Shen, Lingyi, Yang, Xianjiong, Huang, Yali, Xu, Hong, Wu, Ning, Zhang, Qilong, Redshaw, Carl
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8434039/
https://www.ncbi.nlm.nih.gov/pubmed/34500750
http://dx.doi.org/10.3390/molecules26175320
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author Wu, Shouting
Liang, Xi
Luo, Fang
Liu, Hua
Shen, Lingyi
Yang, Xianjiong
Huang, Yali
Xu, Hong
Wu, Ning
Zhang, Qilong
Redshaw, Carl
author_facet Wu, Shouting
Liang, Xi
Luo, Fang
Liu, Hua
Shen, Lingyi
Yang, Xianjiong
Huang, Yali
Xu, Hong
Wu, Ning
Zhang, Qilong
Redshaw, Carl
author_sort Wu, Shouting
collection PubMed
description 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 (1)H and (13)C 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.
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spelling pubmed-84340392021-09-12 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 Molecules Article 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 (1)H and (13)C 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. MDPI 2021-09-01 /pmc/articles/PMC8434039/ /pubmed/34500750 http://dx.doi.org/10.3390/molecules26175320 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wu, Shouting
Liang, Xi
Luo, Fang
Liu, Hua
Shen, Lingyi
Yang, Xianjiong
Huang, Yali
Xu, Hong
Wu, Ning
Zhang, Qilong
Redshaw, Carl
Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives
title Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives
title_full Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives
title_fullStr Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives
title_full_unstemmed Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives
title_short Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives
title_sort synthesis, crystal structure and bioactivity of phenazine-1-carboxylic acylhydrazone derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8434039/
https://www.ncbi.nlm.nih.gov/pubmed/34500750
http://dx.doi.org/10.3390/molecules26175320
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