Steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone: A convenient synthesis, antiproliferation activity, structure-activity relationships, and role of heterocyclic moiety

Abstract

A series of steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone were designed and prepared by a convenient heterocyclization reaction. The in vitro anticancer activities for these obtained compounds were evaluated against human cancer cell lines (HepG2, Huh-7, and SGC-7901), which demonstrated that some of these heterocyclic pyrimidine derivatives exhibited significantly good cytotoxic activities against all tested cell lines compared with 5-fluorouracil (5-FU), especially, compound 3b exhibited high potential growth inhibitory activities against all tested cell lines with the IC50 values of 5.41 ± 1.34, 5.65 ± 1.02 and 10.64 ± 1.49 μM, respectively, which might be used as promising lead scaffold for discovery of novel anticancer agents.

Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells

“…Steroid 2g was selected as the lead compound against MDA-MB-231. High antiproliferative activity of chlorine-containing steroids was also reported in the study [92]. The steroidal [17,16-d]pyrimidine derivative containing the 2-chlorophenyl moiety displayed a significant cytostatic effect in the cell lines HepG2 (human hepatocellular liver carcinoma cell line) and Huh7 (human hepatoma cell line) with IC 50 values lower than 6 µM.…”

Retracted Article: The synthesis and biological activity of marine alkaloid derivatives and analogues

“…Natural products are always present in small amounts in nature, so in order to obtain large amounts of these compounds it is impossible to extract them from their sources. [164][165][166][167] The use of synthetic methods changes this situation, and a large number of desired target compounds can be obtained through synthesis, and then applied to relevant research or used directly as drugs. Xu et al 168 used pityriacitrin as the lead compound to modify its structure to obtain a large number of cytotoxic compounds.…”

Steroidal Pyrimidines and Dihydrotriazines as Novel Classes of Anticancer Agents against Hormone-Dependent Breast Cancer Cells

“…This line of research has been extensively developed in recent years. In 2017, Ke et al designed novel steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone and evaluated their in vitro inhibitory activity against liver and gastric cancer cells (Ke et al, 2017 ). Briefly, 16 steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone were designed and synthesized via a sequence transformation, and their activities were assessed by MTT.…”