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, 3,6,7,8,9,10,11,12,1 3,14,15,16,17-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.

Green Synthesis of Benzo or Cyclopenta[j][1,7]phenanthroline Derivatives in EtOH under Catalyst‐free Conditions

“…Therefore, a number of procedures have been reported to prepare these potential active heterocycles in recent years . Of which, quinolin‐6‐amine is an important reactant to the synthesis of [4,7]phenanthroline derivatives , such as benzo[ b ][4,7]phenanthroline, cyclopenta[ b ][4,7]phenanthroline, and indeno[2,1‐ b ][4,7]phenanthroline.…”