A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis
作者： Cristina Lemini , Elia Cruz–Ramos , Rubén Alfredo Toscano , Raymundo Cruz–Almanza
DOI: 10.1016/S0039-128X(98)00063-4
关键词:
摘要: Abstract The epimers 17β-amino-1,3,5(10)-estratrien-3-ol and 17α-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17β-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone–oxime. 17α-amino epimer obtained from estradiol, via tosylate, followed nucleophilic displacement sodium azide subsequent reduction with LiAlH4. They characterized spectroscopic methods. Determination crystal structures 3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-α-amino-1,3,5(10)-estratriene hydrochloride, 17β-acetylamino-1,3,5(10)-estratriene-3-ol, 3-acetoxy-17β-acetylamino-1,3,5(10)-estratriene enabled us to characterize structure 17α 17β amino for first time.
elsevier.com
sci-hub.se 参考文章(22)
Henri Brunner, Gerhard Sperl, Synthese und Antitumoraktivität voncis-Dichloroplatin(II)-Komplexen mit Östradiolderivaten Monatshefte Fur Chemie. ,vol. 124, pp. 83- 102 ,(1993) , 10.1007/BF00808513
Z. Szendi, G. Dombi, I. Vincze, STEROIDS, LIII: NEW ROUTES TO AMINOSTEROIDS Monatshefte Fur Chemie. ,vol. 127, pp. 1189- 1196 ,(1996) , 10.1007/BF00844694
Cristina Lemini, Consuelo Rubio-Póo, Griselda Silva, Juana Garcia-Mondragon, Elvira Zavala, Nicandro Mendoza-Patiño, Dolores Castro, Raymundo Cruz-Almanza, Juan Jose Mandoki, Anticoagulant and estrogenic effects of two new 17β-aminoestrogens, butolame [17β-(4-hydroxy-1-butylamino)-1, 3,5(10)-estratrien-3-ol] and pentolame [17β-(5-hydroxy-1-pentylamino)-1, 3,5(10)-estratrien-3-ol] Steroids. ,vol. 58, pp. 457- 461 ,(1993) , 10.1016/0039-128X(93)90002-5
Peter Kaspar, Herbert Witzel, Steroid binding to the cytosolic estrogen receptor from rat uterus. influence of the orientation of substituents in the 17-position of the 8β- and 8α-series Journal of Steroid Biochemistry. ,vol. 23, pp. 259- 265 ,(1985) , 10.1016/0022-4731(85)90403-0
D. Cremer, J. A. Pople, General definition of ring puckering coordinates Journal of the American Chemical Society. ,vol. 97, pp. 1354- 1358 ,(1975) , 10.1021/JA00839A011
Erich Hecker, Elisabeth Walk, Zur Chemie der p‐Chinole, III. o‐Chinon‐diacetate und weitere Aminoanaloge der natürlichen Östrogene Chemische Berichte. ,vol. 93, pp. 2928- 2937 ,(1960) , 10.1002/CBER.19600931226
A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92 – a program for automatic solution of crystal structures by direct methods Journal of Applied Crystallography. ,vol. 27, pp. 435- 435 ,(1994) , 10.1107/S002188989400021X
L. Goodfriend, A. H. Sehon, PREPARATION OF AN ESTRONE–PROTEIN CONJUGATE Biochemistry and Cell Biology. ,vol. 36, pp. 1177- 1184 ,(1958) , 10.1139/O58-128
Claude Chavis, Chantal de Gourcy, Jean-Louis Borgna, Jean-Louis Imbach, New steroidal nitrosoureas Steroids. ,vol. 39, pp. 129- 147 ,(1982) , 10.1016/0039-128X(82)90081-2
Irén Vincze, László Hackler, Zsuzsa Szendi, Gyula Schneider, Steroids 54. Amino acylamidosteroids. Steroids. ,vol. 61, pp. 697- 702 ,(1996) , 10.1016/S0039-128X(96)00202-4