TY - JOUR
T1 - Design and synthesis of new steroid-oxazin derivative using some strategies
AU - Figueroa-Valverde, Lauro
AU - Díaz-Cedillo, Francisco
AU - García-Cervera, Elodia
AU - Pool-Gómez, Eduardo
AU - Rosas-Nexticapa, Marcela
AU - López-Ramos, Maria
AU - Hau-heredia, Lenin
AU - Sarabia-Alcocer, Betty
N1 - Publisher Copyright:
© 2014, Chemical Publishing Co. All rights reserved.
PY - 2014
Y1 - 2014
N2 - In this study, a steroid-oxazin derivative was synthesized using several strategies; the first stage involve the reaction of β-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-(1Hnaphtho[ 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.
AB - In this study, a steroid-oxazin derivative was synthesized using several strategies; the first stage involve the reaction of β-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-(1Hnaphtho[ 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.
KW - Ethylenediamine
KW - Oxazin
KW - Steroid
KW - β-naphthol
UR - http://www.scopus.com/inward/record.url?scp=84907810480&partnerID=8YFLogxK
U2 - 10.14233/ajchem.2014.16411
DO - 10.14233/ajchem.2014.16411
M3 - Artículo
SN - 0970-7077
VL - 26
SP - 6417
EP - 6419
JO - Asian Journal of Chemistry
JF - Asian Journal of Chemistry
IS - 19
ER -