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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Research Article

Synthesis of New A-CD Estrogenic Compounds: D-Homo-analogs Lacking B-ring

Author(s): Armin Dadgar, Abbas Shafiee and Latifeh Navidpour

Volume 20, Issue 25, 2016

Page: [2735 - 2741] Pages: 7

DOI: 10.2174/1385272820666160525142520

Price: $65


Prolonged exposure to estrogens as hormone replacement therapy agents to relieve menopausal symptoms is linked to an increased risk of breast and other types of human cancers. Previous studies showed the carcinogenic effect of estrogens occurred through formation of carcinogenic/tumor initiating quinone metabolites. Hence, it was found that occupying both ortho-positions by substituents on the A-ring effectively prevent the quinone formation. Hence, a new substituted phenolic series of A-CD estrogen family, where the five-membered Dring is substituted with a six-membered one, was designed and synthesized. Desired compounds were prepared by stereospecific reduction of Wieland-Miescher ketone followed by coupling with lithiated protected phenols. Dehydration of corresponding alcohols afforded the alkene intermediates. Final hydrogenation removed the protecting group and selectively reduced the double bond to give the desired 9-(S)-isomer.

Keywords: 17β-Estradiol, A-CD analogs, non-quinone forming ligands, stereoselectivity, wieland-miescher ketone, carcinogenicity.

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