title: Efficient synthesis of 'redox-switched' naphthoquinone thiol-crown ethers and their biological activity evaluation.
abstract: Series of naphthoquinone thiol-crown ethers had been prepared. The antibacterial, antifungal, and cytotoxic activities of these synthetic naphthoquinone thiol-crown ethers were investigated. All of the compounds tested displayed antibacterial, cytotoxic and antifungal activities. The bis-naphthoquinone thiol-crown ether 7a was the most potent inhibitor among tested analogues against Staphylococcus aureus methicillin resistance with MIC value of 2.68 microM.
authors.affiliation: Department of Biochemistry, Taipei Medical University, Taipei, Taiwan.
authors.forename: Sheng Tung
authors.initials: ST
authors.lastname: Huang
authors.forename: Hsien Shou
authors.initials: HS
authors.lastname: Kuo
authors.forename: Chiao Long
authors.initials: CL
authors.lastname: Hsiao
authors.forename: Yuh Ling
authors.initials: YL
authors.lastname: Lin
mesh_terms: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D005658:Fungi / Q000187:drug effects; D006801:Humans; D007928:Lethal Dose 50; D016106:Methicillin Resistance; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship; D018675:Toxicity Tests; D014407:Tumor Cells, Cultured
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D004988:Ethers, Cyclic; D009285:Naphthoquinones