TY - JOUR
T1 - Reactions of 3,4-estrone quinone with mimics of amino acid side chains
AU - Abul-Hajj, Yusuf J
AU - Tabakovic, Katmerka
AU - Gleason, William B.
AU - Ojala, William H.
PY - 1996/3
Y1 - 1996/3
N2 - 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.
AB - 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.
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U2 - 10.1021/tx950146p
DO - 10.1021/tx950146p
M3 - Article
C2 - 8839046
AN - SCOPUS:0029949186
SN - 0893-228X
VL - 9
SP - 434
EP - 438
JO - Chemical research in toxicology
JF - Chemical research in toxicology
IS - 2
ER -