Generic placeholder image

Medicinal Chemistry


ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Research Article

Synthesis of Some Steroidal Derivatives with Side Chain of 20- and 22- Hydrazone Aromatic Heterocycles and their Antiproliferative Activity

Author(s): Chunfang Gan, Liang Liu, Jianguo Cui*, Zhiping Liu, Haixin Shi, Qifu Lin, Haibing Sheng, Chunhui Yang and Yanmin Huang*

Volume 13, Issue 4, 2017

Page: [375 - 383] Pages: 9

DOI: 10.2174/1573406413666161205121039

Price: $65


Background: The modification of steroidal structure is commonly used to change the biological activity of steroids in medicinal chemistry. Some steroids containing heterocycles exhibit distinct cytotoxicity against various cancer cell lines and have been receiving wide attention over the years by medicinal chemists for drug discovery.

Methods: Using pregnenolone and stigmasterol as starting materials, via different chemical reaction, two series of heterosteroids with side chain of 20- and 22-hydrazone aromatic cycles or heterocycles in their structures were synthesized and characterized by IR, NMR and HRMS. The antiproliferative activity of the compounds in vitro was evaluated against human HT-29, HeLa, Bel 7404 and SGC 7901 cancer cells by MTT assays.

Results: The steroidal compounds with side chain of 20-hydrazone aromatic cycles or heterocycles exhibited distinct cytotoxicity. However, analogues with the side chain of 22-hydrazone resulted in a dramatic decrease of the cytotoxicity. The result of Annexin V assay showed that the 20-hydrazone compounds were potent apoptotic inducers against these carcinoma cells.

Conclusion: Steroidal compounds with the side-chain of 20-hydrazone aromatic heterocycles exhibit distinct antiproliferative activity in vitro. However, the compounds with the side-chain of 22-hydrazone aromatic heterocycle decreased the cytotoxicity of the compounds.

Keywords: Antiproliferative activity, cytotoxicity, hydrazones, pregnenolone, 22-seco-stigmastan-22-al.

Graphical Abstract

Rights & Permissions Print Export Cite as
© 2023 Bentham Science Publishers | Privacy Policy