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Bioorg Med Chem. 2013 Apr 1;21(7):1925-43. doi: 10.1016/j.bmc.2013.01.041. Epub 2013 Jan 31.

Stereoselective synthesis of a new class of potent and selective inhibitors of human Δ8,7-sterol isomerase.

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  • 1Ludwig-Maximilians University, Department of Pharmacy, Center for Drug Research, Butenandtstr. 5-13, 81377 Munich, Germany.


Starting from Grundmann's ketone a new chemotype of inhibitors of the post-squalene part of cholesterol biosynthesis was developed. Stereoselective introduction of an angular methyl group at C-3a, followed by a plethora of functionalisations at C-4 and C-5 led to cis-configured amino alcohols as a new chemotype of inhibitors of cholesterol biosynthesis. In cell-based screening systems these compounds were identified to be selective inhibitors of human Δ8,7-sterol isomerase, inhibiting total cholesterol biosynthesis with IC50 values in the low nanomolar range. The most active compounds did not affect fungal Δ8,7-sterol isomerase (in ergosterol biosynthesis), neither showed noteworthy antimicrobial and cytotoxic effects.

Copyright © 2013 Elsevier Ltd. All rights reserved.

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