title: Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones.
abstract: An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (μg·mL(-)(1)) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (μg·mL(-)(1)) against Staphylococcus aureus.
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
authors.forename: Jiang-Kun
authors.initials: JK
authors.lastname: Dai
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
authors.forename: Wen-Jia
authors.initials: WJ
authors.lastname: Dan
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
authors.forename: Na
authors.initials: N
authors.lastname: Li
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
authors.forename: Hong-Tao
authors.initials: HT
authors.lastname: Du
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China.
authors.forename: Ji-Wen
authors.initials: JW
authors.lastname: Zhang
authors.affiliation: College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. Electronic address: wangjunru@nwsuaf.edu.cn.
authors.forename: Jun-Ru
authors.initials: JR
authors.lastname: Wang
mesh_terms: D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D013203:Staphylococcal Infections / Q000188:drug therapy; D013211:Staphylococcus aureus / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D002243:Carbolines; D026121:Indole Alkaloids; C453379:canthin-6-one
keywords: 3-N-alkylation; 3-N-benzylation; Antibacterial; Canthin-6-one; Staphylococcus aureus; Structure–activity relationship; Synthesis