Reactions of 3,4-estrone quinone with mimics of amino acid side chains

Yusuf J Abul-Hajj, Katmerka Tabakovic, William B. Gleason, William H. Ojala

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

Reaction of 3,4-estrone o-quinone (3,4-EQ) with several amino acid side chain mimics, including 4-ethylphenol, 4-methylimidazole, acetic acid, and propanethiol, gave a mixture of several products including the catechol, Michael addition products, and dimeric products of the catechol. On the other hand, several other amino acid side chain mimics, including ethanol, acetamide, 1-ethylguanidine, and 3-methylindole, did not result in any addition products or catechol formation. Michael additions to 3,4-EQ with 4- methylimidazole, acetate, and 4-ethyl phenoxide resulted in 1,4-addition, leading to C-1 adducts while reaction with propanethiol gave the C-2 addition product.

Original languageEnglish (US)
Pages (from-to)434-438
Number of pages5
JournalChemical research in toxicology
Volume9
Issue number2
DOIs
StatePublished - Mar 1996

Fingerprint Dive into the research topics of 'Reactions of 3,4-estrone quinone with mimics of amino acid side chains'. Together they form a unique fingerprint.

  • Cite this

    Abul-Hajj, Y. J., Tabakovic, K., Gleason, W. B., & Ojala, W. H. (1996). Reactions of 3,4-estrone quinone with mimics of amino acid side chains. Chemical research in toxicology, 9(2), 434-438. https://doi.org/10.1021/tx950146p