title: Synthesis and biological evaluation of 2,6-dichloropurine bicyclonucleosides containing a triazolyl-carbohydrate moiety.
abstract: A series of bicyclic nucleosides containing a triazolyl-carbohydrate moiety were synthesized and their antitumor activity in vitro for human cancer cell lines was also tested. Compound 11 was synthesized efficiently with 3,6-anhydro sugar 7 as raw material, while compound 7 was prepared from 1,2;5,6-di-O-isopropylidene-α-d-glucose. Compounds 12a-e were synthesized by treating compound 11 with alkynes, catalyzed by copper(I). After removal of the acetyl protecting groups, the target compounds 5a-e showed significant inhibitory activity against EC109, PC-3, MGC-803, and HGC-7 cell lines.
authors.affiliation: School of Pharmaceutical Sciences and New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450001, PR China.
authors.forename: Qiurong
authors.initials: Q
authors.lastname: Zhang
authors.forename: Peng
authors.initials: P
authors.lastname: He
authors.forename: Guangqiang
authors.initials: G
authors.lastname: Zhou
authors.forename: Yifei
authors.initials: Y
authors.lastname: Gu
authors.forename: Ting
authors.initials: T
authors.lastname: Fu
authors.forename: Dengqi
authors.initials: D
authors.lastname: Xue
authors.forename: Hong-Min
authors.initials: HM
authors.lastname: Liu
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002241:Carbohydrates / Q000737:chemistry; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011687:Purines / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D002241:Carbohydrates; D009705:Nucleosides; D011687:Purines; C031268:2,6-dichloropurine
keywords: 1,3-Dipolar cycloaddition; Anti-tumor activity; Bicyclic nucleosides