title: Synthesis and antimicrobial activity of polyhalo isophthalonitrile derivatives.
abstract: A series of polyhalo isophthalonitrile derivatives (3 and 4) that incorporate a variety of substituents at the 2-, 4-, 5- and/or 6-positions of the isophthalonitrile moieties have been designed and synthesized. These derivatives were evaluated for their antimicrobial activity against Staphylococcus aureus, Bacillus cereus (Gram-positive bacteria), Escherichia coli, Pseudomonas aeruginosa (Gram-negative bacteria); and Candida albicans (Fungi). Compounds 3 and 4 showed stronger inhibition of Gram-positive bacteria and fungi growth, and the antimicrobial ability of compound 3j (a 4-(benzylamino)-5-chloro-2,6-difluoro analog, MIC[SA] = 0.5 μg/mL; MIC[BC] = 0.4 μg/mL; MIC[CA] = 0.5 μg/mL) were close to nofloxacin and fluconazole and identified as the most potent antimicrobial agents in the series. The preliminary analysis of structure-activity relationships is also discussed.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Yunnan University, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Chao
authors.initials: C
authors.lastname: Huang
authors.forename: Sheng-Jiao
authors.initials: SJ
authors.lastname: Yan
authors.forename: Neng-Qin
authors.initials: NQ
authors.lastname: He
authors.forename: Ya-Juan
authors.initials: YJ
authors.lastname: Tang
authors.forename: Xing-Hong
authors.initials: XH
authors.lastname: Wang
authors.forename: Jun
authors.initials: J
authors.lastname: Lin
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D000935:Antifungal Agents; D009570:Nitriles