Design and Synthesis of Naphthalene-Pregnen Derivative Using Some Strategies

Abstract

In this study, a naphthalene-pregnen derivative was synthesized using several strategies. The first step was achieved by the synthesis of 3,5-bis(2-naphthyloxy)benzoic acid (2) via displacement of nitro group from 3,5-dinitrobenzoic acid. In the second stage, N-(2-amino-ethyl)-3,5-bis-(naphthalen-2-yloxy)benzamide (4) was synthesized by the reaction of 2 with ethylenediamine using boric acid as catalyst. Also 4 was developed by the reaction of N-(2-aminoethyl)-3,5-dinitrobenzamide with b-naphthol in presence of dimethyl sulfoxide. Third stage, was achieved by preparation of 3,20-bis-{2-[3,5-bis-(naphthalen-2-yloxy)benzoylamino]ethylimino}pregnene (5) by the reaction of 4 with progesterone using boric acid as catalyst. Additionally 5 was prepared by the reaction of N-[2-(1-{3-[2-(2,4-dinitro-benzenecarbonylamino)ethylimino]-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}-ethylideneamino)ethyl]-2,4-di-nitro-benzamidewith b-naphthol in presence of dimethyl sulfoxide. Finally, other experiment involves the synthesis of 4-chloro-1-{(2-[3,5-bis-(naphthalen-2-yloxy)benzoylamino])ethyl}-1H,2H-spiro[azetidine-3,3´-17-(4-chloro-1-methyl-3-oxo-2-{(2-[3,5-bis-(naphthalene-2-yloxy)benzoylamino])ethyl}-2-aza-cyclobutyl)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren]-2-one by the reaction of 5 with chloroacetyl chloride in the presence of triethylamine. The structure of all compounds obtained was confirmed by spectroscopic and spectrometric methods.