776318-00-4Relevant academic research and scientific papers
Neighboring group participation: Part 15. Stereoselective synthesis of some steroidal tetrahydrooxazin-2-ones, as novel presumed inhibitors of human 5α-reductase
Woelfling, Janos,Hackler, Laszlo,Mernyak, Erzsebet,Schneider, Gyula,Toth, Istvan,Szecsi, Mihaly,Julesz, Janos,Sohar, Pal,Csampai, Antal
, p. 451 - 460 (2007/10/03)
During the alkaline methanolysis of 3β-acetoxy-21-chloromethyl-pregn- 5-ene-20β-N-phenylurethane, and its p-substituted phenyl derivatives, cyclization occurs, in the course of which 17β-[3-(N-phenyl) tetrahydrooxazin-2-on-6-yl]androst-5-en-3β-ol and its p-substituted phenyl derivatives are formed. The cyclization takes place with (N--6) neighboring group participation. Oppenauer oxidation of the 3β-hydroxy-exo- heterocyclic steroids yielded the corresponding Δ4-3- ketosteroids. The structures of the new compounds were proved by IR, 1H and 13C NMR spectroscopy, using up-to-date measuring techniques such as 2D-COSY, HMQC, and HMBC. The inhibitory effects (CI 50) of the Δ4-3-ketosteroids on 5α-reductase were studied.
