title: Regioselective synthesis of novel 3-alkoxy (phenyl) thiophosphorylamido-2-(per-O-acetylglycosyl-1'-imino)thiazolidine-4-one derivatives from O-alkyl N4-glycosyl(thiosemicarbazido)phosphonothioates.
abstract: A series of 3-alkoxy(phenyl)thiophosphorylamido-2-(per-O-acetylglycosyl-1'-imino)thiazolidine-4-one derivatives were prepared by the reaction of 1-alkoxy(phenyl)thiophosphoryl-4-(per-O-acetylglycosyl) thiosemicarbazides with ethyl bromoacetate. (1)H/(13)C HMBC measurements corroborated by X-ray crystallographic results revealed the exclusive regioselectivity of these ring closures toward the N-2 position of the thiosemicarbazide moiety. The bioactivity data of 3a-k suggest that the thiazolidine-4-one ring is critical for the herbicidal and fungicidal activities.
authors.affiliation: State Key laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Yu Xin
authors.initials: YX
authors.lastname: Li
authors.forename: Hao An
authors.initials: HA
authors.lastname: Wang
authors.forename: Xiao Ping
authors.initials: XP
authors.lastname: Yang
authors.forename: Hai Ying
authors.initials: HY
authors.lastname: Cheng
authors.forename: Zhi Hong
authors.initials: ZH
authors.lastname: Wang
authors.forename: Yi Ming
authors.initials: YM
authors.lastname: Li
authors.forename: Zheng Ming
authors.initials: ZM
authors.lastname: Li
authors.forename: Su Hua
authors.initials: SH
authors.lastname: Wang
authors.forename: Dong Wen
authors.initials: DW
authors.lastname: Yan
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012663:Semicarbazides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D006540:Herbicides; D012663:Semicarbazides; D053778:Thiazolidines; C005151:thiosemicarbazide