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Vol. 26 No. 19 (2014): Vol 26 Issue 19

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Design and Synthesis of New Steroid-Oxazin Derivative Using Some Strategies

https://doi.org/10.14233/ajchem.2014.16411
Figueroa-Valverde Lauro
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Diaz-Cedillo Francisco
Facultad de Nutrición, Universidad Veracruzana, Médicos y Odontologos s/n C.P. 91010, Unidad del Bosque Xalapa, Veracruz, México
Garcia-Cervera Elodia
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Pool-Gomez Eduardo
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Rosas-Nexticapa Marcela
Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala s/n Col. Santo Tomas, México, D.F. C.P. 11340
Lopez-Ramos Maria
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Hau-Heredia Lenin
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México
Sarabia-Alcocer Betty
Faculty of Medicine, University Autonomous of Campeche, Av. Patricio Trueba deRegil s/n, Col Lindavista C.P. 24090 Campeche Cam., México

Corresponding Author(s) : Figueroa-Valverde Lauro

lauro_1999@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19

Abstract

In this study, a steroid-oxazin derivative was synthesized using several strategies; the first stage involve the reaction of b-naphthol with ethylenediamine in presence of formaldehyde to form the compound 3 (3-(1H-naphtho[1,2-e][1,3]oxazin-2(3H)-yl)propan-1-amine). The second stage was achieved by reaction of 3 with dehydroisoandrosterone 3-sulfate to form the compound 5 (10,13-dimethyl-17-[2-(1H-naphtho[1,2-e][1,3]oxazin-2-yl)-ethylimino]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3-sulfonic acid) using boric acid as catalyst. Finally, the third stage involve the synthesis of 17-{(3-chloro-2-oxo-cyclobutyl)-[2-(1H-naphtho[1,2-e][1,3]oxazin-2-yl)-ethyl]amino}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3-sulfonic acid (7) by reaction of 5 with chloroacetyl chloride in presence of triethylamine. The structure of compounds obtained was confirmed by elemental analysis, spectroscopy and spectrometry data. In conclusion, this method offers some advantages such as good yields, simple procedure, low cost and ease of workup.

Keywords

Steroid Oxazin Ethylenediamine β-naphthol
Lauro, F.-V., Francisco, D.-C., Elodia, G.-C., Eduardo, P.-G., Marcela, R.-N., Maria, L.-R., … Betty, S.-A. (2014). Design and Synthesis of New Steroid-Oxazin Derivative Using Some Strategies. Asian Journal of Chemistry, 26(19), 6417–6419. https://doi.org/10.14233/ajchem.2014.16411
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