Synthesis And Antiproliferative Activity Of 3-Hydroxyl-3-Methoxymethyl-5-Pregnan-20-One With A C-21 Hydrophilic Substituent
HETEROATOM CHEMISTRY(2017)
Abstract
A series of 3-hydroxyl-3-methoxymethyl-5-pregnan-20-ones 7-15 possessing C-21 hydrophilic substituents were synthesized from the corresponding C21-bromo steroid 6 in 24%-89% yields. The hydrophilic groups include amino group from Delepine reaction, hydroxyl group from the hydrolysis by cesium formate in anhydrous MeOH, and amino acids, hydrazinecarboxamide, piperazine, and imidazolyl from nucleophilic substitution. Acylation and O-glycosylation of the resulting C-21 hydroxylsteroid also afforded the corresponding acylated and glycosylated products in excellent yield (77%-89%). Among the compounds, aminosteroid 7 and piperazinyl steroid 14 were most potent against the proliferation of human prostate cancer PC-3 cells with IC50 values of 42 and 82molL(-1), respectively.
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Key words
-bromoketones, 21-bromo-3-hydroxyl-3-methoxymethyl-5-pregnan-20-one, amino acids, hydrophilic, O-glycosylation
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