Synthesis,Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives |
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| Authors: | Shouting Wu Xi Liang Fang Luo Hua Liu Lingyi Shen Xianjiong Yang Yali Huang Hong Xu Ning Wu Qilong Zhang Carl Redshaw |
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| Affiliation: | 1.Research Center for Molecular Medical Engineering, Department of Basic Medical Sciences, Guizhou Medical University, Guiyang 550004, China; (S.W.); (X.L.); (L.S.); (X.Y.); (Y.H.); (H.X.);2.Department of Biology & Engineering, Guizhou Medical University, Guiyang 550004, China; (F.L.); (H.L.);3.Department of Chemistry, University of Hull, Cottingham Road, Hull HU6 7RX, UK; |
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| 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. |
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| Keywords: | phenazine-1-carboxylic acid acylhydrazone compounds crystal structure anticancer activity |
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