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

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), Article 5320. 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