Rational design and syntheis of substrate-based inhibitors of steroidogenesis

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Title: Rational design and syntheis of substrate-based inhibitors of steroidogenesis
Author: Liu, Jialin
Abstract: Sterol biosynthesis is crucial to all groups of life forms . Targeted inhibition of this pathway by substrate -based analogs is currently used to probe sterol function and may have therapeutic importance . In this dissertation , a series of new steroidal triperpenes with a modified lanosterol or cycloartenol frame have been designed to inhibit steroidogenesis . These compounds , along with a number of known sterol biosynthesis inhibitors with the cholestane skeleton , have been prepared and characterized in detail using GC , MS , HPLC and NMR . Notably , a series of substrate analogs constructed with a methyl , nitrogen , sulfur , bromine or fluorine atom or altered to possess a methylene cyclopropane , or elongated to contain a terminal double or triple bonds were prepared to act as mechanism -based inactivators of the sterol 24 -methyl transferase enzyme . In addition , compounds with the cholestane and lanostane structures were prepared with modifications at C -7 and C -32 to be reversible and irreversible inhibitors of the ¦¤8 - ¦¤7 -isomerase and 14¦Á -demethylase enzymes , respectively .
URI: http : / /hdl .handle .net /2346 /16839
Date: 2008-12

Citation

Rational design and syntheis of substrate-based inhibitors of steroidogenesis. Doctoral dissertation, Texas Tech University. Available electronically from http : / /hdl .handle .net /2346 /16839 .

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