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The Synthesis of (E)-4-Thio-5-(2-Bromovinyl)Uridine/Deoxyuridine and Its Characterization and Cytotoxicity

Zhang, Xiaohui; Yan, Defeng; Ma, Kedong; He, Lingshuang; Gao, Ruiqi; Xu, Yaozhong and Li, Depeng (2016). The Synthesis of (E)-4-Thio-5-(2-Bromovinyl)Uridine/Deoxyuridine and Its Characterization and Cytotoxicity. Chinese Journal of Organic Chemistry, 36(12) pp. 2989–2996.

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(E)-4-Thio-5-(2-brominevinyl)uridine/2'-deoxyuridine(8a/8b) were efficiently and in an environmental friendly way synthesized from uridine/2'-deoxyuridine (1a/1b) that were first transformed to (E)-(2-brominevinyl) uridine / 2'-deoxyuridine(5a/5b) via iodination, selective oxidation, Heck reaction steps. The resulting products (5a/5b) were then converted to the targets (8a/8b) through esterification, thio-reaction of carbonyl, hydrolysis steps. Two new compounds (8a/8b) and three new intermediates (7a 7b 10) were obtained, and their structures have been fully characterized by 1H NMR, 13C NMR, IR, UV, HR-MS, X-Ray. The study of 8a and their derivatives regarding cytotoxicity was carried out by using MTT experiment method, and the initial findings suggest (E)-4-Thio-5-(2-brominevinyl) uridine/ 2'-deoxyuridine (8a / 8b) would be potential antitumor drugs.

Item Type: Journal Item
Copyright Holders: 2016 Chinese Chemical Society & SIOC, CAS
ISSN: 0253-2786
Keywords: (E)-4-Thio-5-(2-bromovinyl)-uridine; (E)-4-Thio-5-(2-bromovinyl)-2'-deoxyuridine; synthesis; cytotoxicity
Academic Unit/School: Faculty of Science, Technology, Engineering and Mathematics (STEM) > Life, Health and Chemical Sciences
Faculty of Science, Technology, Engineering and Mathematics (STEM)
Item ID: 47279
Depositing User: Yao Xu
Date Deposited: 14 Sep 2016 09:00
Last Modified: 01 May 2019 19:56
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