title: Iodine-catalyzed direct C-H thiolation of imidazo[1,5-a]quinolines for the synthesis of 3-sulfenylimidazo[1,5-a]quinolines.
abstract: An iodine-catalyzed regioselective sulfenylation of imidazo[1,5-a]quinolines was developed under metal- and oxidant-free reaction conditions. Using disulfides or thiophenols as sulfenylating agents, 3-sulfenylimidazo[1,5-a]quinoline derivatives were obtained in good to excellent yields with broad functional group tolerance. A multi-component reaction to generate 1-sulfenylated imidazo[1,5-a]pyridines is also described. Preliminary biological evaluation showed that some of the 3-sulfenylated imidazo[1,5-a]quinolines had significant anticancer activity.
authors.affiliation: School of Chemical Engineering, Anhui University of Science and Technology, Huainan, Anhui 232001, PR China. fengct2010@163.com.
authors.forename: Song-Song
authors.initials: SS
authors.lastname: Wu
authors.forename: Cheng-Tao
authors.initials: CT
authors.lastname: Feng
authors.forename: Di
authors.initials: D
authors.lastname: Hu
authors.forename: Ye-Kai
authors.initials: YK
authors.lastname: Huang
authors.forename: Zhong
authors.initials: Z
authors.lastname: Li
authors.forename: Zai-Gang
authors.initials: ZG
authors.lastname: Luo
authors.forename: Shi-Tang
authors.initials: ST
authors.lastname: Ma
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D011804:Quinolines; D013438:Sulfhydryl Compounds; D007455:Iodine