Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803 |
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| Authors: | Chun Li Zhengfeng Yang Fan Yang Mingyao Liu Jie Tang |
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| Affiliation: | a Institute of Medicinal Chemistry, Department of Chemistry, Institute of Biomedical Sciences, School of Life Sciences, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China
b PPSM, Institut d’Alembert, ENS Cachan, CNRS, UniverSud, 61 av President Wilson, F-94230 Cachan, France |
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| Abstract: | A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803. |
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| Keywords: | Trimethylaluminium 1,6-Conjugate addition α-Methyl steroid β-Methyl steroid Stereoselectivity Human gastric cancer cell line MGC-803 |
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