AI Article Synopsis
- Researchers synthesized novel difluorovinyl steroids as potential inhibitors of the enzyme C17(20) lyase, which is essential for testosterone production.
- The method involved using a reagent to react with 17-acetyl steroids to create these compounds.
- An interesting byproduct, abnormal Wittig products, emerged during the synthesis, and the resulting difluoroolefin was identified as a moderately potent, time-dependent inhibitor of the target enzyme.
Article Abstract
Novel 21,21-difluorovinyl steroids, designed as difluorinated C20(21) enol mimics of pregnenolone, were targeted as potential mechanism-based inhibitors of C17(20) lyase, a crucial enzyme in the biosynthesis of testosterone. Addition of (difluoromethyl)diphenylphosphine oxide reagent to 17-acetyl steroids was the approach chosen for the construction of these compounds. Of particular interest were the abnormal Wittig products which formed during attempted preparation of the triene 9. The target difluoroolefin 3 was found to be a moderately potent, time-dependent inhibitor of the enzyme.
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| http://dx.doi.org/10.1016/s0968-0896(02)00434-0 | DOI Listing |
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