Azido analogs of neuroactive steroids

Steroids

Volumn 76, Issue 10-11, 2011, Pages 1043-1050

  Vidrna, Lukáǎ ^a   Černý, Ivan ^a   Pouzar, Vladimír ^a   Borovská, Jiřina ^b   Vyklický, Vojtěch ^b   Vyklický Jr , Ladislav ^b   Chodounská, Hana ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF MATHEMATICS   (Czech Republic)

Author keywords

Azides; Neuroactive steroids; NMDA receptor; Synthesis

Indexed keywords

(20) 20 AZIDO 5BETA PREGNAN 3ALPHA YL ACETATE; (20) 20 AZIDO 5BETA PREGNAN 3ALPHA YL SULFATE PYRIDINIUM SALT; (20) 20 HYDROXY 5BETA PREGNAN 3ALPHA YL ACETATE DERIVATIVE; (20) 5BETA PREGNAN 3ALPHA,20 DIYL 3 ACETATE 20 TOSYLATE; 17ALPHA AZIDO 5BETA ANDROSTAN 3 ONE; 17ALPHA AZIDO 5BETA ANDROSTAN 3ALPHA OL; 17ALPHA AZIDO 5BETA ANDROSTAN 3ALPHA YL SULFATE PYRIDINIUM SALT; 17ALPHA HYDROXY 5BETA ANDROSTAN 3 ONE; 17BETA AZIDO 5BETA ANDROSTAN 3 ONE; 17BETA AZIDO 5BETA ANDROSTAN 3ALPHA OL; 17BETA AZIDO 5BETA ANDROSTAN 3ALPHA YL SULFATE PYRIDINIUM SALT; 20 AZIDO 21 NOR 5BETA PREGNAN 3 ONE; 20 AZIDO 21 NOR 5BETA PREGNAN 3ALPHA OL; 20 AZIDO 21 NOR 5BETA PREGNAN 3ALPHA YL SULFATE PYRIDINIUM SALT; 20 AZIDO 5BETA PREGNAN 3ALPHA OL; 20 HYDROXY 21 NOR 5BETA PREGNAN 3 ONE; 3 OXO 21 NOR 5BETA PREGNAN 20 YL PIVALATE; 3 OXO 21 NOR 5BETA PREGNAN 20 YL TOSYLATE; 3 OXO 5BETA ANDROSTAN 17ALPHA YL TOSYLATE; 3 OXO 5BETA ANDROSTAN 17BETA YL TOSYLATE; 3ALPHA HYDROXY 5ALPHA PREGNAN 20 ONE; 5BETA ANDROSTANOLONE; AZIDE; GLUTAMIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; SODIUM AZIDE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; ASSAY; CHEMICAL MODIFICATION; CHEMICAL PARAMETERS; CHEMICAL REACTION; CONTROLLED STUDY; EMBRYO; HUMAN; HUMAN CELL; KIDNEY CELL; MITSUNOBU REACTION; NERVOUS SYSTEM; SYNTHESIS;

DIOSCOREACEAE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEROIDS;

EID: 79960440314     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.04.008     Document Type: Article

References (33)

1. A.C. Campbell, M.S. Maidment, J.H. Pick, and G.F. Woods Aminosteroids. Part 8. Synthesis of the four isomeric 3,7-diamino-5α-pregnanes J Chem Soc, Perkin Trans 1 1982 1783 1789
2. A.P. Davis, and M.G. Orchard Stereocontrolled synthesis of cholic acid derivatives with N-protected 7β- and/or 12β-amino substituents Tetrahedron Lett 33 1992 5111 5112
3. I. Černý, V. Pouzar, O. Lapčík, and R. Hampl Addition of azoimide to unsaturated ketones in the steroid series. Synthesis of N-(17β-hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic acid and its evaluation as hapten for dihydrotestosterone immunoanalysis Collect Czech Chem Commun 62 1997 1931 1939 (Pubitemid 127405273)
4. I. Černý, M. Buděšínský, V. Pouzar, and P. Drašar Linear chaining of etienic acid derivatives with the amide bond. Synthesis of oligomeric steroids Collect Czech Chem Commun 66 2001 933 946
5. A receptor: synthesis, activity and cytotoxicity Collect Czech Chem Commun 69 2004 1506 1516 (Pubitemid 39221227)
6. C. Djerassi, A. Moscowitz, K. Ponsold, and G. Steiner Optical rotary dispersion studies CIX. An octant rule for the azide J Am Chem Soc 89 1967 347 352
7. O.E. Edwards, J.L. Douglas, D.C. Horwell, W. Rank, and T. Sano Thermal and photochemical reactions of steroidal α-azido ketones Can J Chem 70 1992 2405 2412 (Pubitemid 23015760)
8. D.H.R. Barton, and L.R. Morgan Jr. 117. Photochemical transformations. Part XII. The photolysis of azides J Chem Soc 1962 622 631
9. A. Pancrazi, and Q. Khuong-Huu Photochimie d'azido-steroides Tetrahedron 31 1975 2041 2048
10. J. Wölfling, Oravecz ÉA, D. Ondré, E. Mernyák, G. Schneider, and I. Tóth Stereoselective synthesis of some 17β-dihydrooxazinyl steroids, as novel presumed inhibitors of 17α-hydroxylase-C17,20-lyase Steroids 71 2006 809 816 (Pubitemid 44062604)
11. M. Felici, R.J.M. Nolte, M.C. Feiters, P. Contreras-Carballada, R.M. Williams, and J.M.M. Smits Cationic heteroleptic cyclometalated iridium(III) complexes containing phenyl-triazole and triazole-pyridine clicked ligands Molecules 15 2010 2039 2059
12. R. Glaser, and E.J. Gabbay Synthesis and characterization of C3 and C17 steroidal amines J Org Chem 35 1970 2907 2912
13. M.I. Merlani, L.S. Amiranashvili, K.G. Mulkidzhanyan, A.R. Shelar, and F.V. Manvi Synthesis and antituberculosis activity of certain steroidal derivatives of the 5α-series Chem Nat Compd 44 2008 618 620
14. C.H. Robinson, C. Ermann, and D.P. Hollis The synthesis of 17α-amino-5-androsten-3β-ol; N.M.R. spectra of 17-substituted androstanes Steroids 6 1965 509 518
15. H.B. Henbest, and J.W.R. ackson The use of aprotic solvents for nucleophilic substitution reactions at C(3) and C(17) in steroids J Chem Soc 1962 954 959
16. T. Shimizu, T. Ohzeki, K. Hiramoto, N. Hori, and T. Nakata Chloromethanesulfonate as an efficient leaving group: rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles Synthesis 1999 1373 1385 (Pubitemid 29450715)
17. T. Nambara, T. Shibata, M. Mimura, and H. Hosoda Synthesis of N-(steroid-17-yl)-maleimide Chem Pharm Bull 19 1971 954 958
18. H. Loibner, and E. Zbiral Reaktionen mit phosphororganischen Verbindungen XLII. Nucleophile Substitutionen an Hydroxysteroiden mit Hilfe von Triphenylphosphan/Azodicarbonsaureester Helv Chim Acta 60 1977 417 425
19. M. Leboeuf, A. Cave, and R. Goutarel Alcaloides steroidiques LIX. Influence de la nature des solvants sur la mecanisme et la stereochimie de l'azidolyse des tosyloxy-20 β steroides. Application a la synthese d'amino-20 α steroides Bull Soc Chim France 6 1967 2100 2104
20. R. Goutarel, C. Conreur, L. Djakouré, M. Leboeuf, and A. Cavé Alcaloides stéroidiques - LXXVII: syntheses de mono- et di-amines stéroidiques. Alcaloides A (saracodine) et B (saracocine) du Sarcococca pruniformis lindl Tetrahedron 24 1968 7013 7026
21. M. Leboeuf, A. Cave, and R. Goutarel Alcaloides steroidiques LXXXVI. Substitutions, eliminations et transpositions des tosyloxy-20 steroides. 1er partie: role de l'hexamethylphosphotriamide (HMPT) dans la substitution et l'elimination Bull Soc Chim France 5 1969 1619 1624
22. R.B. Gabbard, and A. Segaloff Facile preparation of 17β-hydroxy- 5β-androstan-3-one and its 17α- methyl derivatives J Org Chem 27 1962 655 656
23. 3H]-labelled epitestosterone and its metabolites Collect Czech Chem Commun 58 1993 600 611
24. V. Pouzar, I. Černý, and P. Drašar Acrylate side chain derivatives of 5β-steroids Collect Czech Chem Commun 58 1993 2963 2976
25. E. Šťastná, I. Černý, V. Pouzar, and H. Chodounská Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction Steroids 75 2010 721 725
26. L.F. Fieser, and M. Fieser Reagents for Organic Synthesis 1 1967 446
27. I. Yoshizawa, R. Oh'Uchi, K. Nagata, S. Itoh, and N. Kawahara Isolation and structural elucidation of the degradation products of pregnanediol disulfate obtained by hot acid hydrolysis Chem Pharm Bull 30 1982 2474 2486 (Pubitemid 13232669)
28. O. Cais, M. Sedlacek, M. Horak, I. Dittert, and L. Vyklicky Jr. Temperature dependence of NR1/NR2B NMDA receptor channels Neuroscience 151 2008 428 438
29. M. Petrovic, M. Sedlacek, M. Horak, H. Chodounska, and L. Vyklicky Jr. 20-Oxo-5β-pregnan-3α-yl sulfate is a use-dependent NMDA receptor inhibitor J Neurosci 25 2005 8439 8450 (Pubitemid 41324730)
30. J.A. Dodge, and C.W. Lugar III. Alcohol inversion of 17β-steroids Bioorg Med Chem Lett 6 1996 1 2
31. P. Tapolcsányi, J. Wölfling, E. Mernyák, and G. Schneider The Mitsunobu inversion reaction of sterically hindered 17-hydroxy steroids Monatsh Chem 135 2004 1129 1136 (Pubitemid 39286494)
32. J.-M. Vatle 2-(Prenyloxymethyl)benzoyl (POMB) group: a new temporary protecting group removable by intramolecular cyclization Tetrahedron 63 2007 10921 10929
33. E. Šťastná, H. Chodounská, V. Pouzar, V. Kapras, J. Borovská, and O. Cais Synthesis of C3 C5, and C7 pregnane derivatives and their effect on NMDA receptor responses in cultured rat hippocampal neurons Steroids 74 2009 256 263