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 sid e chain mimics, including 4-ethylphenol, 4-methylimidazole, acetic aci d, and propanethiol, gave a mixture of several products including the catechol, Michael addition products, and dimeric products of the catec hol. On the other hand, several other amino acid side chain mimics, in cluding ethanol, acetamide, 1-ethylguanidine, and 3-methylindole, did not result in any addition products or catechol formation. Michael add itions to 3,4-EQ with 4-methylimidazole, acetate, and 4-ethyl phenoxid e resulted in 1,4-addition, leading to C-l adducts while reaction with propanethiol gave the C-2 addition product.