title: Regioselective synthesis of novel 3-thiazolidine acetic acid derivatives from glycosido ureides.
abstract: A series of 3-thiazolidine acetic acid-2-(per-O-acetylglycosyl)-1'-imino-α-(substituted)-4-oxo ethyl ester derivatives (3a-t) were prepared via the reaction of substituted amino acid-N-[(per-O-acetylglycosylamino)thioxomethyl]-ethyl ester with ethyl bromoacetate. The crystal structure of 3-thiazolidine acetic acid-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactoyranosyl)-1'-imino-α-methyl-4-oxo ethyl ester 3g and ¹H-¹³C HMBC (2D NMR experiments) measurements of 3-thiazolidine acetic acid-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1'-imino-α-(1-methylthio)ethyl-4-oxo ethyl ester 3j revealed the exclusive regioselectivity during the closure of these rings toward the N-2 position of the thiourea moiety. Furthermore, the crystal structure of compound 3g showed that the attack of N-1 was blocked by sugar ring owing to the steric effect. The bioactivity data suggested that compound 2e has mild anticancer activity.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China. liyx128@nankai.edu.cn
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Li
authors.forename: Wei
authors.initials: W
authors.lastname: Chen
authors.forename: Xiaoping
authors.initials: X
authors.lastname: Yang
authors.forename: Guanping
authors.initials: G
authors.lastname: Yu
authors.forename: Mingzhen
authors.initials: M
authors.lastname: Mao
authors.forename: Yunyun
authors.initials: Y
authors.lastname: Zhou
authors.forename: Tuanwei
authors.initials: T
authors.lastname: Liu
authors.forename: Zhengming
authors.initials: Z
authors.lastname: Li
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D004952:Esters / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D013237:Stereoisomerism; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000085:Acetates; D000970:Antineoplastic Agents; D004952:Esters; D006027:Glycosides; D006842:Hydrocarbons, Brominated; D053778:Thiazolidines; D014508:Urea; C010144:ethyl bromoacetate