Estrogen quinones: reaction with propylamine.
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.
Khasnis
D
D
Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis 55455.
Abul-Hajj
Y J
YJ
D004963:Estrenes / Q000737:chemistry / Q000378:metabolism*; D004970:Estrone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D008239:Lysine / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011437:Propylamines / Q000737:chemistry / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet
D004963:Estrenes; D011437:Propylamines; D004970:Estrone; C086810:estra-1(10),4-diene-2,3,17-trione; C044208:1,5(10)-estradiene-3,4,17-trione; D008239:Lysine