Navegar

Colección

Datos Estadísticas

Artículo

La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

In this paper we report the use of an intramolecular Ugi reaction to synthesize new 4-azacholestanes diversely substituted both at N-4 and C-5. Both the scope and the stereochemical outcome of this approach were studied by varying the nature of the components necessary for this multicomponent reaction. In sight of our results we concluded that this methodology can be applied to obtain 4-azasteroids targeted to find new biologically active compounds. © 2008 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of 4-azasteroids by an intramolecular Ugi reaction
Autor:Alonso, F.; Acebedo, S.L.; Bruttomesso, A.C.; Ramírez, J.A.
Filiación:Departamento de Quimica Organica and UMYMFOR (CONICET-Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellon 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Palabras clave:4-Azacholestanes; Azasterols; Multicomponent reaction; Ugi reaction; 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
Año:2008
Volumen:73
Número:12
Página de inicio:1270
Página de fin:1276
DOI: http://dx.doi.org/10.1016/j.steroids.2008.06.002
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:Azasteroids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v73_n12_p1270_Alonso

Referencias:

  • Morzycki, J.W., Wawer, I., Gryszkiewicz, A., Maj, J., Siergiejczyk, L., Zaworska, A., 13C-NMR study of 4-azasteroids in solution and solid state (2002) Steroids, 67, pp. 621-626
  • Rasmusson, G.H., Reynolds, G.F., Steinberg, N.G., Walton, E., Patel, G.F., Liang, T., Azasteroids: structure-activity relationships for inhibition of 5α-reductase, and of androgen receptor binding (1986) J Med Chem, 29, pp. 2298-2315
  • Burbiel, J., Bracher, F., Azasteroids as antifungal (2003) Steroids, 68, pp. 587-594
  • Zhu, J., Bienyamé, H., (2005) Multicomponet reactions, , Wiley-VCH Verlag GmbH & Co., Weinheim
  • Dömling, A., Recent developments in isocyanide based multicomponent reactions in applied chemistry (2006) Chem Rev, 106, pp. 17-89
  • Marcaccini, S., Pepino, R., Torroba, T., Miguel, D., García-Valverde, M., Synthesis of thiomorpholines by an intramolecular Ugi reaction (2002) Tetrahedron Lett, 43, pp. 8591-8593
  • Sung, K., Wu, S.-H., Chen, P.-I., Facile two-pot syntheses of novel alternating benzene/imidazole systems (2002) Tetrahedron, 58, pp. 5599-5602
  • Edward, J.T., Holder, D., Lunn, W.H., Puskas, I., Oxidation of cholest-4-en-3-one with periodate-permanganate (1961) Can J Chem, 39, pp. 599-600
  • SYBYL 7.3, Tripos International, 1699 South Hanley Rd., St. Louis, MO 63144, USA; Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998) Gaussian 98 (Revision A.7), , Gaussian, Inc., Pittsburgh, PA
  • Marcaccini, S., Torroba, T., The use of the Ugi four-component condensation (2007) Nat Protocols, 2, pp. 632-639
  • Banfi, L., Basso, A., Guanti, G., Riva, R., Assymetric isocyanide-based MCRs (2005) Multicomponet reactions, , Zhu J., and Bienyamé H. (Eds), Wiley-VCH Verlag GmbH & Co., Weinheim

Citas:

---------- APA ----------
Alonso, F., Acebedo, S.L., Bruttomesso, A.C. & Ramírez, J.A. (2008) . Synthesis of 4-azasteroids by an intramolecular Ugi reaction. Steroids, 73(12), 1270-1276.
http://dx.doi.org/10.1016/j.steroids.2008.06.002
---------- CHICAGO ----------
Alonso, F., Acebedo, S.L., Bruttomesso, A.C., Ramírez, J.A. "Synthesis of 4-azasteroids by an intramolecular Ugi reaction" . Steroids 73, no. 12 (2008) : 1270-1276.
http://dx.doi.org/10.1016/j.steroids.2008.06.002
---------- MLA ----------
Alonso, F., Acebedo, S.L., Bruttomesso, A.C., Ramírez, J.A. "Synthesis of 4-azasteroids by an intramolecular Ugi reaction" . Steroids, vol. 73, no. 12, 2008, pp. 1270-1276.
http://dx.doi.org/10.1016/j.steroids.2008.06.002
---------- VANCOUVER ----------
Alonso, F., Acebedo, S.L., Bruttomesso, A.C., Ramírez, J.A. Synthesis of 4-azasteroids by an intramolecular Ugi reaction. Steroids. 2008;73(12):1270-1276.
http://dx.doi.org/10.1016/j.steroids.2008.06.002