title: A practical regioselective synthesis of alkylthio- or arylthioindoles without the use of smelly compounds such as thiols.
abstract: A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C(3)-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C(2)-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toho University, Chiba, Japan.
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Hamashima
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Mori
authors.forename: Kazunori
authors.initials: K
authors.lastname: Sawada
authors.forename: Yuko
authors.initials: Y
authors.lastname: Kasahara
authors.forename: Daisuke
authors.initials: D
authors.lastname: Murayama
authors.forename: Yuto
authors.initials: Y
authors.lastname: Kamei
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Okuno
authors.forename: Yuusaku
authors.initials: Y
authors.lastname: Yokoyama
authors.forename: Hideharu
authors.initials: H
authors.lastname: Suzuki
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D019281:Dimerization; D007211:Indoles / Q000737:chemistry*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D007211:Indoles; D013438:Sulfhydryl Compounds; C030374:indole