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The oxidation of the ring A of 16α,17α-cyclohexanoprogesterone gave 5-oxo-A-nor-3,5-secopregnan-3-oic acid. The subsequent ring A closure in the latter compound upon treatment with sodium acetate in Ac2O afforded 4-oxasteroid. The… Click to show full abstract
The oxidation of the ring A of 16α,17α-cyclohexanoprogesterone gave 5-oxo-A-nor-3,5-secopregnan-3-oic acid. The subsequent ring A closure in the latter compound upon treatment with sodium acetate in Ac2O afforded 4-oxasteroid. The reaction with ammonium acetate in acetic acid produced 4-azasteroid. Antiproliferative activity of the resulting steroids against cervical cancer HeLa cells and the in vitro binding to the progesterone receptor were studied. The compounds cause a statistically significant decrease in viability of cervical cancer HeLa cells, having no effect on normal skin fibroblasts. The tested steroids show very low binding to the rat uterine progesterone receptor.
Journal Title: Russian Chemical Bulletin
Year Published: 2018
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