Title:Synthesis of Some Steroidal Derivatives with Side Chain of 20- and 22- Hydrazone Aromatic Heterocycles and their Antiproliferative Activity
Volume: 13
Issue: 4
Author(s): Chunfang Gan, Liang Liu, Jianguo Cui*, Zhiping Liu, Haixin Shi, Qifu Lin, Haibing Sheng, Chunhui Yang and Yanmin Huang*
Affiliation:
- College of Chemistry and Material Science, Guangxi Teachers and Education University, 530001, Nanning,China
- College of Chemistry and Material Science, Guangxi Teachers Education University, Nanning 530001,China
Keywords:
Antiproliferative activity, cytotoxicity, hydrazones, pregnenolone, 22-seco-stigmastan-22-al.
Abstract: 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.
