Design and synthesis of a new androgen derivative using some strategies

Abstract

Anew androgen derivative was synthesized using some strategies; in the first stage the compound of N-(1,10-phenanthrolin-5-ylmethyl)ethane-1,2-diamine (3)was obtained by the reaction of 1,10-phenanthroline with ethylenediamine in presence of formaldehyde. The second stage was achieved by the reaction of 3 with testosterone using boric acid as catalyst to form the compound 10,13-dimethyl-3-{2-[([1,10]phenanthrolin-5-ylmethyl)-amino]-ethylimino}-2,3,6, 7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol (5). Finally, the compound 7 (Chloro-acetic acid 3-((3-chloro-2-oxo-cyclobutyl)- {2-[(3-chloro-2-oxo-cyclobutyl)-[1,10]phenanthrolin-5-ylmethyl-amino]ethyl} -amino)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H- cyclopenta[a]phenanthren-17-yl ester was synthesized by thereaction of 5 with chloroacetyl chloride in presence of triethylamine. The structure of the compounds obtained was confirmed by elemental analysis, spectroscopy and spectrometry data. The proposed method offers some advantages such as good yields, simple procedure, low cost, and ease of workup.