Synthesis and biological evaluation of chalcone derivatives containing aminoguanidine or acylhydrazone moieties

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• 作者：Zhi-Yu Wei^a ; Ke-Qiang Chi^b ; Zhan-Kui Yu^a ; Hong-Yan Liu^a ; Liang-Peng Sun^a ; Chang-Ji Zheng^a ; ^{zhengcj@ybu.edu.cn} ; Hu-Ri Piao^a ; ^{piaohuri@yahoo.com.cn}
• 关键词：Chalcone ; Acylhydrazone ; Aminoguanidine ; Antibacterial activity ; Antifungal activity ; Anti-inflammatory activity ; Cytotoxicity
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 December 2016
• 年：2016
• 卷：26
• 期：24
• 页码：5920-5925
• 全文大小：486 K
• 卷排序：26

文摘

Three novel series of chalcone derivatives containing an aminoguanidine or acylhydrazone moiety were designed, synthesized and evaluated in terms of their antibacterial, antifungal and anti-inflammatory activities. Most of the synthesized compounds showed potent inhibitory activity towards various bacteria and one fungus with minimum inhibitory concentrations (MICs) ranging from 1 to 8 μg/mL. Compared with our previously reported chalcone derivatives (MICs >64 μg/mL), these compounds exhibited improved antibacterial activities (MICs = 2 μg/mL) against Gram-negative bacterial strains (Escherichia coli 1924 and 1356). Compounds 4f and 4h were found to be the most potent with an MIC value of 1 μg/mL against the Gram-negative bacterial strains Salmonella typhimurium 1926 and the fungus Candida albicans 7535. In addition, compound 4f displayed the most potent anti-inflammatory activity of all of the compounds prepared in the current study with 92.45% inhibition after intraperitoneal administration, making it more potent than the reference drugs indomethacin and ibuprofen. The cytotoxic activity of the compound 4f was assessed in HeLa, Hep3B and L02 cells.