Synthesis and biological evaluation of 17β-alkoxyestra-1,3,5(10)-trienes as potential neuroprotectants against oxidative stress

L. Prokai, S. M. Oon, K. Prokai-Tatrai, K. A. Abboud, J. W. Simpkins

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

17β-O-Alkyl ethers (methyl, ethyl, propyl, butyl, hexyl, and octyl) of estradiol were obtained from 3-O-benzyl-17β-estradiol with sodium hydride/alkyl halide, followed by the removal of the O-benzyl protecting group via catalytic transfer hydrogenation. An increase compared to estradiol in the protection of neural (HT-22) cells against oxidative stress due to exposure of glutamate was furnished by higher (C-3 to C-8) alkyl ethers, while methyl and ethyl ethers decreased the neuroprotective effect significantly. Lipophilic (butyl and octyl) ethers blocking the phenolic hydroxyl (3-OH) of A-ring were inactive.

Original languageEnglish
Pages (from-to)110-114
Number of pages5
JournalJournal of Medicinal Chemistry
Volume44
Issue number1
DOIs
StatePublished - 4 Jan 2001

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