Synthesis and molecular modeling of (4′R)- and (4′S)- 4′-substituted 2′-{[(E)-androst-5-en-17-ylidene]-methyl}oxazolines

Add time:08/07/2019    Source:sciencedirect.com

Synthesis of four novel (4′R)- and (4′S)- 2′-{[(E)-3β-hydroxyandrost-5-en-17-ylidene]-methyl} oxazolines, comprising 4′-hydroxymethyl (1 and 2) and 4′-methoxycarbonyl (3 and 4) substituents is presented. Reaction of 17α-bromo-21-iodo-3β-acetoxypregn-5-en-20-one with either (L)-serine methyl ester, or (D)-serine methyl ester resulted in methyl N-[3β-acetoxy-21-oxopregna-5,17(20)-dien-21-yl]-(L)-serinate and methyl N-[3β-acetoxy-21-oxopregna-5,17(20)-dien-21-yl]-(D)-serinate (as mixtures of related [17(20)E]- and [17(20)Z]-isomers). Cyclization of obtained amides led to methyl 2′-{[(E)-3β-acetoxyandrost-5-en-17-ylidene]methyl}-(4′S)-4′,5′-dihydro-1′,3′-oxazole-4′-carboxylate and methyl 2′-{[(E)-3β-acetoxyandrost-5-en-17-ylidene]methyl}-(4′R)-4′,5′-dihydro-1′,3′-oxazole-4′-carboxylate which were transformed to titled compounds 1–4. The molecular docking of compounds 1–4 to ligand binding site of nuclear receptor LXRβ revealed significant differences due to stereochemical configuration of 4′ atom and structure of 4′-substituent.

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