Reactions of 3,4-estrone quinone with mimics of amino acid side chains.
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 addition 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.
Abul-Hajj
Y J
YJ
Department of Medicinal Chemistry, University of Minnesota, Minneapolis 55455, USA.
Tabakovic
K
K
Gleason
W B
WB
Ojala
W H
WH
D000596:Amino Acids / Q000737:chemistry*; D004963:Estrenes / Q000737:chemistry* / Q000633:toxicity*; D008956:Models, Chemical
D000596:Amino Acids; D004963:Estrenes; C044208:1,5(10)-estradiene-3,4,17-trione