title: Synthesis and biological evaluation of chalcone derivatives containing aminoguanidine or acylhydrazone moieties.
abstract: 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 8μg/mL. Compared with our previously reported chalcone derivatives (MICs >64μg/mL), these compounds exhibited improved antibacterial activities (MICs=2μg/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 1μg/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.
authors.affiliation: Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University College of Pharmacy, Yanji, Jilin Province 133002, PR China.
authors.forename: Zhi-Yu
authors.initials: ZY
authors.lastname: Wei
authors.affiliation: Medical College of Dalian University, Dalian, Liaoning Province 116622, PR China.
authors.forename: Ke-Qiang
authors.initials: KQ
authors.lastname: Chi
authors.affiliation: Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University College of Pharmacy, Yanji, Jilin Province 133002, PR China.
authors.forename: Zhan-Kui
authors.initials: ZK
authors.lastname: Yu
authors.affiliation: Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University College of Pharmacy, Yanji, Jilin Province 133002, PR China.
authors.forename: Hong-Yan
authors.initials: HY
authors.lastname: Liu
authors.affiliation: Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University College of Pharmacy, Yanji, Jilin Province 133002, PR China.
authors.forename: Liang-Peng
authors.initials: LP
authors.lastname: Sun
authors.affiliation: Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University College of Pharmacy, Yanji, Jilin Province 133002, PR China. Electronic address: zhengcj@ybu.edu.cn.
authors.forename: Chang-Ji
authors.initials: CJ
authors.lastname: Zheng
authors.affiliation: Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University College of Pharmacy, Yanji, Jilin Province 133002, PR China. Electronic address: piaohuri@yahoo.com.cn.
authors.forename: Hu-Ri
authors.initials: HR
authors.lastname: Piao
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D002599:Chalcone / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006146:Guanidines / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D006835:Hydrazones / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000935:Antifungal Agents; D006146:Guanidines; D006835:Hydrazones; D002599:Chalcone; C004479:pimagedine
keywords: Acylhydrazone; Aminoguanidine; Anti-inflammatory activity; Antibacterial activity; Antifungal activity; Chalcone; Cytotoxicity