Synthesis of 4-azasteroids by an intramolecular Ugi reaction

Steroids

Volumn 73, Issue 12, 2008, Pages 1270-1276

  Alonso, Fernando ^a   Acebedo, Sofía L ^a   Bruttomesso, Andrea C ^a   Ramírez, Javier A ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

4 Azacholestanes; Azasterols; Multicomponent reaction; Ugi reaction

Indexed keywords

4 (2' (1H BENZO[B]AZOL 3 YL)ETHYL) 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 (2' (1H BENZO[B]AZOL 3 YL)ETHYL) 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; 4 (2' PHENYLETHYL) 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 (2' PHENYLETHYL) 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; 4 (3' AZIDOPROPYL) 5 N (ETHOXYCARBONYLMETHYLEN)CARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 (3' AZIDOPROPYL) 5 N (ETHOXYCARBONYLMETHYLEN)CARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; 4 BENZYL 5 N (DIETHOXYPHOSPHORYLMETHYLEN)CARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 BENZYL 5 N (DIETHOXYPHOSPHORYLMETHYLEN)CARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; 4 BENZYL 5 N (METHOXYCARBONYLMETHYLEN)CARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 BENZYL 5 N (METHOXYCARBONYLMETHYLEN)CARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; 4 BENZYL 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 BENZYL 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; 4 BUTYL 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 BUTYL 5 N CYCLOHEXYLCARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; 4 PROPARGYL 5 N (ETHOXYCARBONYLMETHYLEN)CARBOXAMIDO 4 AZA 5ALPHA CHOLESTAN 3 ONE; 4 PROPARGYL 5 N (ETHOXYCARBONYLMETHYLEN)CARBOXAMIDO 4 AZA 5BETA CHOLESTAN 3 ONE; AZASTEROID; CHOLESTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; DRUG TARGETING; STEREOCHEMISTRY; SUBSTITUTION REACTION;

AZASTEROIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 50249085956     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.06.002     Document Type: Article

References (12)

1. 13C-NMR study of 4-azasteroids in solution and solid state. Steroids 67 (2002) 621-626
2. Rasmusson G.H., Reynolds G.F., Steinberg N.G., Walton E., Patel G.F., Liang T., et al. Azasteroids: structure-activity relationships for inhibition of 5α-reductase, and of androgen receptor binding. J Med Chem 29 (1986) 2298-2315
3. Burbiel J., and Bracher F. Azasteroids as antifungal. Steroids 68 (2003) 587-594
4. Zhu J., and Bienyamé H. Multicomponet reactions (2005), Wiley-VCH Verlag GmbH & Co., Weinheim
5. Dömling A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106 (2006) 17-89
6. Marcaccini S., Pepino R., Torroba T., Miguel D., and García-Valverde M. Synthesis of thiomorpholines by an intramolecular Ugi reaction. Tetrahedron Lett 43 (2002) 8591-8593
7. Sung K., Wu S.-H., and Chen P.-I. Facile two-pot syntheses of novel alternating benzene/imidazole systems. Tetrahedron 58 (2002) 5599-5602
8. Edward J.T., Holder D., Lunn W.H., and Puskas I. Oxidation of cholest-4-en-3-one with periodate-permanganate. Can J Chem 39 (1961) 599-600
9. SYBYL 7.3, Tripos International, 1699 South Hanley Rd., St. Louis, MO 63144, USA.
10. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann Jr. R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe C., Gill P.M.W., Johnson B.G., Chen W., Wong M.W., Andres J.L., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98 (Revision A.7) (1998), Gaussian, Inc., Pittsburgh, PA
11. Marcaccini S., and Torroba T. The use of the Ugi four-component condensation. Nat Protocols 2 (2007) 632-639
12. Banfi L., Basso A., Guanti G., and Riva R. Assymetric isocyanide-based MCRs. In: Zhu J., and Bienyamé H. (Eds). Multicomponet reactions (2005), Wiley-VCH Verlag GmbH & Co., Weinheim