AI Article Synopsis
- Researchers developed testosterone analogs using a specific compound containing a 13,14-secosteroidal fragment.
- The key processes included removing iodine from the compound in a controlled manner and protecting a specific keto group.
- The new analogs, which have flexible structures, are useful for studying their biological effects compared to traditional testosterone and other steroids with a more rigid structure.
Article Abstract
A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6beta-methoxy-3alpha, 5-cyclo-13,14-seco-5alpha-androstan-14,17-dione. The key steps involved stereoselective deiodination of the starting compound with triphenylphosphine and selective protection of the 17-keto group with trimethylsilylcyanide. Removal of iodine at C-13 proceeded with inversion of the configuration at C-13, which has been established by X-ray crystallography. 13,14-Secotestosterone analogues substituted and non-substituted at C-14 have been prepared. The obtained compounds containing flexible CD ring fragments are of great interest for comparative studies in biological tests together with testosterone and other steroids with a rigid tetracyclic skeleton.
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| http://dx.doi.org/10.1016/j.steroids.2004.04.010 | DOI Listing |
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