Lemini C, Cruz-Ramos E, Toscano R A, Cruz-Almanza R
Departamento de Farmacología, Facultad de Medicina, Universidad Nacional Autónoma de México (UNAM), México, D.F., México.
Steroids. 1998 Nov;63(11):556-64. doi: 10.1016/s0039-128x(98)00063-4.
The epimers 17 beta-amino-1,3,5(10)-estratrien-3-ol and 17 alpha-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17 beta-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone-oxime. The 17 alpha-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17 alpha-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-alpha-amino,1,3,5(10)-estratriene hydrochloride, 17 beta-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17 beta-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17 alpha and 17 beta amino epimers for the first time.
合成了差向异构体17β-氨基-1,3,5(10)-雌甾三烯-3-醇和17α-氨基-1,3,5(10)-雌甾三烯-3-醇。17β-氨基-1,3,5(10)-雌甾三烯-3-醇通过雌酮肟的催化氢化制备。17α-氨基差向异构体由雌二醇经对甲苯磺酸酯制得，随后用叠氮化钠进行亲核取代，再用氢化铝锂还原。通过光谱方法对它们进行了表征。对3-(对甲苯磺酰氧基)-17α-1,3,5(10)-雌甾三烯、3-(对甲苯磺酰氧基)-17-α-氨基-1,3,5(10)-雌甾三烯盐酸盐、17β-乙酰氨基-1,3,5(10)-雌甾三烯-3-醇和3-乙酰氧基-17β-乙酰氨基-1,3,5(10)-雌甾三烯的晶体结构测定使我们首次能够表征17α和17β氨基差向异构体的结构。
