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

• Main Authors: Xiao-Han Yuan, Shuai Wang, Xiao-Ning Wang, Bin Yu, Hong-Min Liu
• Format: Article
• Language: English
• Published: Georg Thieme Verlag KG 2021-03-01
• Series: Pharmaceutical Fronts
• Subjects: higher-carbon sugars; nucleosides; uracil; antiproliferative activity
• Online Access: http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1731300

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.