Estrogen Quinones: Reaction with Propylamine

Dipti Khasnis, Yusuf J Abul-Hajj

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Reaction of propylamine with 2,3-estrone o-quinone (2,3-EQ) and 3,4-estrone o-quinone (3,4-EQ) gave a complex mixture of mostly unidentifiable products. Several reaction products were isolated and identified using spectroscopic techniques. With 3,4-EQ, both 1,2- and 1,6-Michael addition reactions were observed in which 4-hydroxyestradiol, an estrogen oxazole, and a violet compound identified as the iminoquinone adduct that was obtained by condensation of one molecule of an estrogen o-aminophenol with the 1,6-Michael addition product of propylamine to 3,4-EQ were identified. Unlike reactions of 3,4-EQ, only 1,2-Michael addition reactions were observed with 2,3-EQ leading to the formation of 2-hydroxyestradiol, two monoiminoquinone compounds, and a bisiminoquinone product.

Original languageEnglish (US)
Pages (from-to)68-72
Number of pages5
JournalChemical research in toxicology
Volume7
Issue number1
DOIs
StatePublished - Jan 1 1994

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