Synthesis and biological evaluation of 2,6-dichloropurine bicyclonucleosides containing a triazolyl-carbohydrate moiety

• Published in: Carbohydrate research Vol. 382; pp. 65 - 70
• Main Authors: Zhang, Qiurong, He, Peng, Zhou, Guangqiang, Gu, Yifei, Fu, Ting, Xue, Dengqi, Liu, Hong-Min
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.12.2013; Elsevier
• Subjects: 1,3-Dipolar cycloaddition; alkynes; Anti-tumor activity; antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Bicyclic nucleosides; Biochemistry & Molecular Biology; Carbohydrates - chemistry; Cell Line, Tumor; Chemistry; Chemistry, Applied; Chemistry, Organic; copper; Drug Screening Assays, Antitumor; Humans; Life Sciences & Biomedicine; Molecular Structure; nucleosides; Nucleosides - chemical synthesis; Nucleosides - chemistry; Nucleosides - pharmacology; Physical Sciences; Purines - chemistry; raw materials; Science & Technology; sugars; 1,3-Dipolar cycloaddition; Bicyclic nucleosides; Anti-tumor activity; IN-VITRO; POTENT; HIV; ANALOGS; NUCLEOSIDES; 1,2,3-TRIAZOLE; INHIBITORS; DERIVATIVES
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2013.10.004

•A series of bicyclonucleosides containing triazolyl-carbohydrate moiety were synthesized.•The target compounds were tested for their in vitro cytostatic activity in different human cancer cells.•The target compounds show significant inhibitory activity against EC109, PC-3, MGC-803, and HGC-7 cell lines. 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.