Design and Synthesis of an Aromatic-steroid Derivative

L. Figueroa ueroaueroa-Valverde alverde^1*, F. Díaz-Cedillo², E. Garc ía-Cervera ervera¹, E. Pool Góme z¹, M. Rosas -Nexticapa ticapa³, M. Lópe z-Ramos¹and I. Mayay-Gil¹

¹Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustín Melgar s/n,Col Buenavista C.P.24039 Campeche Cam., México. ²Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala s/n Col. Santo Tomas, México, D.F. C.P. 11340. ³Facultad de Nutrición, Universidad de Veracruz (Campus Xalapa). Médicos y Odontologos s/n Unidad del Bosque C.P. 91010, Xalapa Veracruz, México. Corresponding author E-mail: lauro_1999@yahoo.com

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ABSTRACT:

In this study, an aromatic derivative was synthetized; the first stage involve the reaction of 3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]-phe-nanthrene-2,4-dicarbaldehyde (compound 1) with ethylenediamine to form 2,4-Bis-[(2-amino-ethylimino)-methyl]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopen- ta[a]phenanthrene-3,17-diol(3) using boric acid as catalyst. The second stage was achieved by the reaction of 3 with 4-hydroxybenzoic acid usingcarbodiimide derivative as catalyst to form the compound 5 (N-(2-{[3,17-Dihydroxy-4-({2-[1-(4-hydroxy-phenyl)vinylamino]-ethyl-imino}-methyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]- phenanthren-2-yl-methylene]-amino}-ethyl)-4-hydroxy-benzamide. 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:

Aromatic steroid derivatives; boric acid and catalyst