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

Author(s): Figueroa-Valverde Lauro, Díaz-Cedillo Francisco, García-Cervera Elodia, Rosas-Nexticapa Marcela, Pool-Gómez Eduardo, Lopéz-Ramos Maria, Camacho-Luis Abelardo

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 8 , 2016


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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

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Article Details

VOLUME: 13
ISSUE: 8
Year: 2016
Published on: 28 November, 2016
Page: [591 - 603]
Pages: 13
DOI: 10.2174/1570178613666160824143943
Price: $65

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