Efficient syntheses of 17-β-amino steroids

Steroids

Volumn 76, Issue 10-11, 2011, Pages 1098-1102

  Taylor, Scott D ^a   Harris, Jesse ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

17 Amino steroids; Catalytic hydrogenolysis; Reductive amination; Sodium triacetoxyborohydride

Indexed keywords

17 AMINO 1,3,5 (10) ESTRATRIEN 3 OL; 17 BETA AMINO STEROID DERIVATIVE; 17BETA ALLYLAMINO 3BETA HYDROXYANDROST 5 ENE; 17BETA AMINO 3BETA HYDROXYANDROST 5 ENE; 17BETA AMINO 5ALPHA ANDROSTAN 3BETA OL; 17BETA BENZYLAMINO 1,3,5 (10) ESTRATRIEN 3 OL; 17BETA BENZYLAMINO 3BETA HYDROXYANDROST 5 ENE; 17BETA BENZYLAMINO 5ALPHA ANDROSTAN 3BETA OL; 17BETA BENZYLAMINO DERIVATIVE; ALLYLAMINE; BENZYLAMINE; DEHYDROEPIANDOSTERONE; EPIANDROSTERONE; ESTRONE; SODIUM TRIACETOXYBOROHYDRIDE; STEROID; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; HYDROGENOLYSIS; REDUCTION; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEROIDS;

EID: 79960458260     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.04.013     Document Type: Article

References (17)

1. M. Mokotoff, M. Zhao, R.J. Marshall, E. Winslow, L.K. Wong, and Q.J. Liao Peptidyl aminosteroids as potential new antiarrhythmic agents Steroids 55 1990 399 404 (Pubitemid 20304400)
2. C. Wang, M. Zhao, J. Yang, and S. Peng Synthesis and analgesic effects of kyotorphin-steroid linkers Steroids 66 2001 811 815 (Pubitemid 32884307)
3. M.A. Fousteris, A.I. Koutsourea, N.P. Lagonikakos, E.S. Arsenou, C. Spyridonidou, and D. Mourelatos Rational design, synthesis and in vitro evaluation of three new alkylating steroidal esters Med Chem 2 2006 569 576 (Pubitemid 44741613)
4. P.K. Li, G.H. Chu, J.P. Guo, A. Peters, and K.W. Selcer Development of potent non-estrogenic estrone sulfatase inhibitors Steroids 63 1998 425 432 (Pubitemid 28292787)
5. O.H. Wheeler, and C. Reyes-Zamora Steroid derivatives of cysteamine and cysteinae Can J Chem 47 1969 160 163
6. J.B. Jones, D.J. Adam, and J.D. Leman Steroids and steroidases. 10. Studies on some potentially antitumor active androstane compounds containing C-17 nitrogen mustard functions J Med Chem 14 1971 827 833
7. M.I. Merlani, L.S. Amiranashvili, K.G. Mulkidzhanyan, and E.P. Kemertelidze Synthesis and biological activity of certain amino-derivatives of 5α-steroids Chem Nat Compd 42 2006 322 324 (Pubitemid 44252975)
8. M.E. Kuehne, E.A. Konopka, and B.F. Lambert Steroidal dihydro-1,3-oxazines as antitumor agents J Med Pharm Chem 51 1962 281 296
9. E. Hecker, and E. Walk o-Chinon-diacetate und weiter Aminoanaloge der naturlichen Ostrogene Chem Ber 93 1960 2928 2937
10. 1H NMR, and X-ray diffraction analysis Steroids 63 1998 556 564 (Pubitemid 28525423)
11. Y. Ye, Y. Huang, Z. Wang, S. Chen, and Y. Tian Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor Steroids 58 1993 35 39
12. P. Kaspar, and H. Witzel Steroid binding to the cytosolic estrogen receptor from rat uterus. Influence of the orientation of substituents in the 17-position of the 8b- and 8a-series J Steroid Biochem 23 1985 259 265 (Pubitemid 15023304)
13. C. Chavis, de Gourcy Ch, J.L. Borgna, and J.L. Imbach New steroidal nitrosoureas Steroids 39 1982 129 147 (Pubitemid 12094886)
14. Z. Szendi, G. Dombi, I. Vincze, and L. Steroids III New routes to amino steroids Monat Chem 127 1996 1189 1196
15. N.S. Nadaraya, V.I. Sladov, E.P. Kemertelidze, and N.N. Suvorov Use of tigogenin for the synthesis of epimers at C3 and C17 of 17-amino-5α- androstan-3-ols Zhurnal Organich Khim 23 1987 533 538
16. H.E. Smith, C.A. Taylor, A.F. McDonagh, and F.-M. Chen Optically active amines. 30. Application of the salicylidenimino chirality rule to aliphatic and alicyclic amines J Org Chem 47 1982 2525 2531
17. A.F. Abdel-Magid, K.G. Carson, B.D. Harris, C.A. Maryanoff, and R.D. Shah Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures J Org Chem 61 1996 3849 3862 (Pubitemid 126532674)