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Vol. 26 No. 4 (2014): Vol 26 Issue 4

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Design and Synthesis of Prednisone Derivatives

https://doi.org/10.14233/ajchem.2014.15818
L. Figueroa-Valverde
Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustin Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., Mexico
F. Diaz-Cedillo
Escuela Nacional de Ciencias Biologicas del Instituto Politecnico Nacional. Prol. Carpio y Plan de Ayala s/n Col. Santo Tomas, D.F. C.P. 11340, Mexico
E. Garcia-Cervera
Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustin Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., Mexico
E. Pool G
Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustin Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., Mexico
M. Rosas-Nexticapa
Facultad de Nutrición, Universidad Veracruzana. Medicos y Odontologos s/n, 91010, Xalapa, Veracruz. Mexico
R. Mendoza-Lopez
Unidad de Servicios de Apoyo en Resolucion Analitica, Universidad Veracruzana. Luis Castelazo Ayala s/n, Col. Industrial Animas, 91190, Xalapa, Veracruz, Mexico
M. Lopez-Ramos
Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustin Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., Mexico
I. May-Gil
Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustin Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., Mexico

Corresponding Author(s) : L. Figueroa-Valverde

lauro_1999@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 4 (2014): Vol 26 Issue 4

Abstract

In this study, some prednisone derivatives were synthesized. The first stage involves the synthesis of 3,11-bis-(2-amino-ethylimino)-17-[1-(2-amino-ethylimino)-2-hydroxyethyl]-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-ol (3) by the reaction of prednisone with ethylenediamine using boric acid as catalyst. The second stage was achieved by reaction of 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4) with the compound 3 using boric acid as catalyst resulting in imino bond formation involved in the compound 2-[3,11-bis-{2-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ylideneamino)}-10,13,17-trimethyl-6,7,8,9,10,11,12,12,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-[2-(1,7,7-trimethyl-bycyclo[2.2.1]hept-2-ylideneamino)ethylimino]ethanol (5). In addition, the third stage was achieved by reaction of compound 3, benzaldehyde and compound 4 using proline as catalyst to form the compound 3-({2-[2-hydroxy-3-(17-hydroxy-3,11-bis[2-(1,7,7-trimethyl-byciclo[2.2.1]heptan-2-one-3-ylenamino)phenyl-methyl]-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15-16,17,-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-propilidene amino]ethyl-amino}phenyl-methyl)-1,7,7-trimethyl-byciclo[2.2.1]heptan-2-one (7). Finally, the four stage was achieved by reaction of 7,7-dimethyl-2-oxobicyclo-[2.2.1]hept-1-yl) methanesulfonic acid, compound 3 and benzaldehyde using proline as catalyst to form the compound 3-({2-[2-hydroxy-3-(17-hydroxy-3,11-bis[2-{7,7-dimethyl-3-(ylenamino-phenyl-methyl)-2-oxo-bicyclo[2.2.1]hept-1-yl}methansulfonic acid]-100,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)propiliden-amino]ethylamino)-7,7-dimethyl-3-(ylenamino-phenyl-methyl)-2-oxo-bicyclo[2.2.1]hept-1-yl-methansulfonic acid] (9).The structure of compounds obtained was confirmed by spectroscopy and spectrometry data.

Keywords

Prednisone Ethylenediamine Proline
Figueroa-Valverde, L., Diaz-Cedillo, F., Garcia-Cervera, E., Pool G, E., Rosas-Nexticapa, M., Mendoza-Lopez, R., … May-Gil, I. (2014). Design and Synthesis of Prednisone Derivatives. Asian Journal of Chemistry, 26(4), 1033–1037. https://doi.org/10.14233/ajchem.2014.15818
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