Modified steroid hormones. 7. 4-Fluoro-17 beta-estradiol: carbon-13 nuclear magnetic resonance, crystal and molecular structure, and biological activity.
The 4-fluoro analogue of 17 beta-estradiol was investigated for estrogenic action in rats by determination of uterine hyperemia and [3H]uridine incorporation and was found to be an active estrogen. Antitumor activity of this analogue was demonstrated against 7,12-dimethylbenz[a]anthracene (DMBA) induced rat mammary adenocarcinoma. Its 13C NMR spectrum was determined, and all signals were assigned. A detailed X-ray diffraction investigation of 4-fluoro-17 beta-estradiol was carried out, and it crystallized in triclinic space group P1 with two steroids and one methanol in a unit cell of a = 7.367 (1), b = 9.363 (6), c = 12.531 (1) A, alpha = 89.31 (3), beta = 93.38 (1), gamma = 109.62 (3) degrees, V = 812.8 A3, and Z = 2. The structure was solved and refined to an R index of 0.062 using 3045 reflections measured on an automated diffractometer. The oxygen atoms at C(3) and C(17) at either ends link the molecules together in a head to tail fashion. The hydroxy groups of the solvent molecules also take part in linking the molecules sideways through the hydroxy groups.
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000037:antagonists & inhibitors; D000230:Adenocarcinoma / Q000139:chemically induced; D000818:Animals; D003461:Crystallography; D004958:Estradiol / Q000031:analogs & derivatives*; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D008325:Mammary Neoplasms, Experimental / Q000139:chemically induced; D051381:Rats; D014599:Uterus / Q000187:drug effects; D014965:X-Rays
C037810:4-fluoroestradiol; D004958:Estradiol; D015127:9,10-Dimethyl-1,2-benzanthracene