Preparation of 5′-deoxy-5′-amino-5′-C-methyl adenosine derivatives and their activity against DOT1L. Issue 22 (15th November 2017)

• Record Type: Journal Article
• Authors: Liu, Tongchao; Xie, Wuchen; Li, Cong; Ren, Huanming; Mao, Yudong; Chen, Guohua; Cheng, Maosheng; Zhao, Dongmei; Shen, Jingkang; Li, Jia; Zhou, Yubo; Xiong, Bing; Chen, Yue-Lei
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 22(2017)
• Page Start: 4960
• Page End: 4963
• Publication Date: 2017-11-15
• Subjects: 5′-Deoxy-5′-amino-5′-C-methyl adenosine derivative -- N-glycosylation -- Nucleoside synthesis -- DOT1L inhibitor -- Structure activity relationship; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.10.019
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: From a readily available 5- C -Me ribofuranoside, we have realized a reliable route to valuable 5′-deoxy-5′-amino-5′- C -methyl adenosine derivatives at gram scale with confirmed stereochemistry. These adenosine derivatives are useful starting materials for the preparation of 5′-deoxy-5′-amino-5′- C -methyl adenosine derivatives with higher complexity. From one of the new adenosine derivatives, some 5′-deoxy-5′-amino-5′- C -methyl adenosine DOT1L inhibitors were prepared in several steps. Data from DOT1L assay indicated that additional 5′- C -Me group improved the enzyme inhibitory activity.