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

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

1, 2,* email and 1,* email
Received: 1 November 2011; in revised form: 14 December 2011 / Accepted: 16 December 2011 / Published: 30 December 2011
(This article belongs to the Special Issue Steroids)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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
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MDPI and ACS Style

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.

AMA Style

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(1):355-368.

Chicago/Turabian Style

Kim, Sujeong; Kim, Yong-ung; Ma, Eunsook. 2012. "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 17, no. 1: 355-368.

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