Abstract
Design and Synthesis of new Steroid-cyclobutanone derivative
1Lauro Figueroa-Valverde*, 2Francisco Díaz-Cedillo, 3Marcela Rosas-Nexticapa, 4Mendoza-López R,1Elodia García-Cervera, 1Eduardo Pool-Gómez1, 1María López-Ramos
DOI : http://dx.doi.org/10.13005/ojc/290309
Abstract:
In this study, a prednisone derivative was synthetized; the first stage involve the reaction of the compound 1 (11-Bis-(2-amino-ethylimino)-17-[1-(2-amino-ethylimino)-2-hydroxy-ethyl]-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phe- nanthren-17-ol)withchloroacetyl chloride in presence of triethylamineto form2[(3-chloro-2-oxo-cyclobutyl)(1-{3,11-bis-(2-[{2-[(chlorocarbonyl)amino]-ethyl}(3-chloro-2-oxocy-clobutyl)amino]-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenantren-17-yl})-2-hydroxyethyl)-amino]ethylcarbamic chloride (3). The second stage was achieved by the reaction of 3 with thiourea in methanol to form the compound 5(2-{(2-Amino-ethyl)-[1-(3,11-bis-[(2-amino-ethyl)-(3-chloro-2-oxo-cyclo- butyl)-amino]-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dode-cahydro-3H-cyclopenta[a]phenantren-17-yl)-2-hydroxy-ethyl]-amino}-4-chloro-cyclobuta-none). The structure of compounds obtainedwas confirmed by elemental analysis, spectroscopy and spectrometry data. In conclusion, this method offers some advantages such as good yields, simple procedure, low cost, and ease of workup.
Keywords:Prednisone;thiourea;chloroacetyl chloride;triethylamine
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