title: Synthesis and antibacterial activity of novel lincomycin derivatives. II. Exploring (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives.
abstract: The synthesis and antibacterial activity of (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives are described. These derivatives were mainly prepared by the Mitsunobu reaction of 2,3,4-tris-O-(trimethylsilyl)lincomycin and the corresponding thiols. Exploring structure-activity relationships of the substituent at the 5 position of a thiadiazole ring revealed that compounds with the ortho substituted phenyl group showed improved antibacterial activities against Streptococcus pneumoniae and Streptococcus pyogenes with erm gene compared with the reported compound (1) that had an unsubstituted benzene ring.
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Ko
authors.initials: K
authors.lastname: Kumura
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Wakiyama
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Kazutaka
authors.initials: K
authors.lastname: Ueda
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Eijiro
authors.initials: E
authors.lastname: Umemura
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Watanabe
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Megumi
authors.initials: M
authors.lastname: Kumura
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Takuji
authors.initials: T
authors.lastname: Yoshida
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd., Yokohama, Japan.
authors.forename: Keiichi
authors.initials: K
authors.lastname: Ajito
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005798:Genes, Bacterial; D008034:Lincomycin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D013296:Streptococcus pneumoniae / Q000187:drug effects* / Q000235:genetics; D013297:Streptococcus pyogenes / Q000187:drug effects / Q000235:genetics*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D008034:Lincomycin