CC BY 4.0 · Pharmaceutical Fronts 2021; 03(01): e18-e22
DOI: 10.1055/s-0041-1731300
Original Article

Synthesis of Natural Product-Like Tricyclic Higher-Carbon Sugar Nucleosides

Xiao-Han Yuan#
1  School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, People's Republic of China
,
Shuai Wang#
1  School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, People's Republic of China
,
Xiao-Ning Wang
2  State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, People's Republic of China
,
Bin Yu
1  School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, People's Republic of China
2  State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, People's Republic of China
3  State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, People's Republic of China
,
Hong-Min Liu
1  School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, People's Republic of China
› Author Affiliations
Funding This work was supported by the National Natural Science Foundation of China (Grant No. 81773562) the Open Fund of State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, China (Grant No. KF-GN-201902), and the Open Project of State Key Laboratory of Natural Medicines (Grant No. SKLNMKF202005).


Abstract

Because of the structural novelty and interesting biological profiles, the synthesis of higher-carbon sugars has been highly pursued. In this work, we first synthesized a series of structurally novel bis-uracil containing tricyclic higher-carbon sugar nucleosides (4a–e) using D-xylose as the starting material and the classical Vorbruggen glycosylation as the key synthetic step. The yields of the target compound were good. Unfortunately, despite the presence of pharmaceutically relevant uracil fragment, compounds 4a–e were inactive against the proliferation of several cancer cell lines (EC109, EC9706, PC-3, and MGC-803). Whether and how 4a–e functioned as anticancer agents would be further studied in our laboratory.

# Xiao-Han Yuan and Shuai Wang contributed equally to this work.




Publication History

Received: 20 April 2021

Accepted: 21 May 2021

Publication Date:
25 June 2021 (online)

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

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