Design and synthesis of prednisone derivatives

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}phenylmethyl)-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.