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Molecules 2012, 17(1), 355-368; doi:10.3390/molecules17010355

Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes

College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea
College of Herbal Bio-industry, Daegu Hany University, Gyeongsangbuk-do 712-715, Korea
Authors to whom correspondence should be addressed.
Received: 1 November 2011 / Revised: 14 December 2011 / Accepted: 16 December 2011 / Published: 30 December 2011
(This article belongs to the Special Issue Steroids)
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The synthesis and evaluation of 5α-reductase inhibitory activity of some 4-azasteroid-20-ones and 20-oximes and 3β-hydroxy-, 3β-acetoxy-, or epoxy-substituted C21 steroidal 20-ones and 20-oximes having double bonds in the A and/or B ring are described. Inhibitory activity of synthesized compounds was assessed using 5α-reductase enzyme and [1,2,6,7-3H]testosterone as substrate. All synthesized compounds were less active than finasteride (IC50: 1.2 nM). Three 4-azasteroid-2-oximes (compounds 4, 6 and 8) showed good inhibitory activity (IC50: 26, 10 and 11 nM) and were more active than corresponding 4-azasteroid 20-ones (compounds 3, 5 and 7). 3β-Hydroxy-, 3β-acetoxy- and 1α,2α-, 5α,6α- or 6α,7α-epoxysteroid-20-one and -20-oxime derivatives having double bonds in the A and/or B ring showed no inhibition of 5α-reductase enzyme.
Keywords: 5α-reductase inhibitor; BPH; 4-azasteroid-20-oxime 5α-reductase inhibitor; BPH; 4-azasteroid-20-oxime

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Kim, S.; Kim, Y.-U.; Ma, E. Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes. Molecules 2012, 17, 355-368.

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