Novel Steroidal[17,16-d]pyrimidines Derived from Epiandrosterone and Androsterone: Synthesis, Characterization and Configuration-Activity Relationships
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Published:2023-03-16
Issue:6
Volume:28
Page:2691
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ISSN:1420-3049
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Container-title:Molecules
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language:en
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Short-container-title:Molecules
Author:
Yang Fei12, Liu Fang2, Min Yong2, Shi Liqiao2, Liu Manli2, Wang Kaimei2ORCID, Ke Shaoyong2ORCID, Gong Yan2, Yang Ziwen12
Affiliation:
1. College of Life Sciences, Wuhan University, Wuhan 430072, China 2. Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China
Abstract
Two series of novel steroidal[17,16-d]pyrimidines derived from natural epiandrosterone and androsterone were designed and synthesized, and these compounds were screened for their potential anticancer activities. The preliminary bioassay indicated that some of these prepared compounds exhibited significantly good cytotoxic activities against human gastric cancer (SGC-7901), lung cancer (A549), and hepatocellular liver carcinoma (HepG2) cell lines compared with 5-fluorouracil (5-FU), epiandrosterone, and androsterone. Especially the respective pairs from epiandrosterone and androsterone showed significantly different inhibitory activities, and the possible configuration-activity relationships have also been summarized and discussed based on kinase assay and molecular docking, which indicated that the inhibition activities of these steroidal[17,16-d]pyrimidines might obviously be affected by the configuration of the hydroxyl group in the part of the steroidal scaffold.
Funder
Program for Leading Talents of Hubei Academy of Agricultural Sciences Innovation and Application of Key Technologies of Quality improving and Efficiency-increasing for the Fengtou Ginger Industry Hubei Agricultural Science Innovation Center Hubei Biopesticide Engineering Research Centre
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
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