Design and Synthesis Three Steroid-Tetraone Derivatives Using Testosterone as Chemical Tool

Abstract

Background: Several steroid derivatives have been prepared using different protocols; however some require special reagents and conditions. The aim of the study involved the synthesis of three steroid-tetraone derivatives using testosterone as building block. Methods: Steroid-tetraone derivatives were prepared by a series of reactions that involve; 1) synthesis of testosterone derivatives (steroid-carbazol or phenylhydrazono-androstanol or steroid-diazepinol) via different conditions; 2) reaction of testosterone derivatives with 3,5-dinitrobenzoic acid in basic medium to form three steroid-ether-nitrobenzoic acid derivatives; 3) synthesis of some steroid-esternitrobenzoic acid derivatives analogs by the reaction of steroidether-nitrobenzoic acid derivatives with 4-hydroxybenzoic acid in presence of DCC; 4) reduction of nitro group with sodium borohydride to form three amino-steroid derivatives; 5) preparation of carboxypropamido-steroid analogs by the reaction of amino-steroid with succinic acid using boric acid as catalyst; and 6) synthesis of steroid-tetraone derivatives by reaction of carboxypropamido-steroid with ethylenediamine in presence of boric acid. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. Results: The 1H NMR spectrum showed signals at 5.50 (CH2-NHCO), 5.68 (Ph-NHCO) and 8.50 ppm (Ph-CONH) for the steroid-tetraone derivatives. Conclusions: In this study were prepared three steroid-tetraone derivatives using several chemical techniques, that they are simple and easy procedures of handling. Keywords: Testosterone, ester, steroid-tetraone, derivative