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Abstract
The acid-catalyzed cyclization of benzylidenes based on 16-dehydropregnenolone acetate (16-DPA) was studied. It was found that these compounds readily undergo regioselective interrupted Nazarov cyclization with trapping chloride ion and an efficient method of the synthesis of d-annulated pentacyclic steroids based on this reaction was proposed. The structures of the synthesized pentacyclic steroids were determined by NMR and X-ray diffraction. It was found that the reaction affords a single diastereomer, but the latter can crystallize as two conformers depending on the structure. Antiproliferative activity of synthesized compounds was evaluated against two breast cancer cell lines: MCF-7 and MDA-MB-231. All tested compounds showed relatively high antiproliferative activity. The synthetic potential of the protocol developed was illustrated by the gram-scale experiment.
Highlights
Steroids are an important class of both natural and synthetic products exhibiting various biological activities [1,2,3,4,5,6,7,8,9,10,11]
[36,37,52,53], we focused on the development of a convenient evaluation of their antitumor activity [36,37,52,53], we focused on the development of a convenient method for the synthesis of D-annulated pentacyclic steroid of the progesterone series IV bearing method for the synthesis of D-annulated pentacyclic steroid of the progesterone series IV bearing the cyclopentanone moiety as an additional ring
We started our research by studying a series of Lewis acids (TiCl4, SnCl4, AlCl3, FeCl3 ) and hydrogen chloride (HCl). 4-Chlorophenyl-substituted dienone 1c was used as a model substrate and dichloromethane, dichloroethane, and benzene as the solvents
Summary
Steroids are an important class of both natural and synthetic products exhibiting various biological activities [1,2,3,4,5,6,7,8,9,10,11]. The chemical modification of steroids is among the most efficient and attractive approaches to the design of new biologically active compounds, including pharmaceuticals [1,2,18,19]. An important application of chemical modification of steroid molecules is to synthesize compounds containing an additional fused ring. It should be noted that some of these compounds exhibit no significant hormonal activity [28,29,30,31] Both heterocyclic analogs I [32,33,34,35,36,37,38,39] and carbocyclic analogs II [40,41] of pentacyclic steroids have attracted considerable attention (Scheme 1)
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