TY - JOUR
T1 - Design and synthesis of some estradiol derivatives using an estradioldicarbaldehyde as chemical tool
AU - Lauro, Figueroa Valverde
AU - Francisco, Díaz Cedillo
AU - Elodia, García Cervera
AU - Marcela, Rosas Nexticapa
AU - Eduardo, Pool Gómez
AU - Maria, Lopéz Ramos
AU - Abelardo, Camacho Luis
N1 - Publisher Copyright:
© 2015 Bentham Science Publishers.
PY - 2015
Y1 - 2015
N2 - In this study some estradiol derivatives were prepared using different strategies. The first stage was achieved by the preparation of an estradiol-dicarbaldehyde derivative (compound 2) by the reaction of estradiol with dimethyl sulfoxide (method A) or with Cooper(II) reagent in the presence of ethylenediamine (method B). The following stage was achieved by synthesis of the steroid-oxadiazin ester derivative (compound 5) using the three-component system (compound 2, urea and anhydride succinic). Later, 5 was reacted with ethylenediamine to form the steroid-amino derivative (compound 6) using boric acid as catalyst. On the other hand, a steroid-acetamide derivative (compound 7) was synthesized by the reaction of 6 with chloroacetyl chloride in the presence of triethylamine. Finally, the compound 7 was reacted with 2-hydroxy-1-naphthaldehyde in basic medium to form a steroid-oxirane carboxamide derivative (compound 8). The structure of all compounds obtained was confirmed by spectroscopic and spectrometric methods.
AB - In this study some estradiol derivatives were prepared using different strategies. The first stage was achieved by the preparation of an estradiol-dicarbaldehyde derivative (compound 2) by the reaction of estradiol with dimethyl sulfoxide (method A) or with Cooper(II) reagent in the presence of ethylenediamine (method B). The following stage was achieved by synthesis of the steroid-oxadiazin ester derivative (compound 5) using the three-component system (compound 2, urea and anhydride succinic). Later, 5 was reacted with ethylenediamine to form the steroid-amino derivative (compound 6) using boric acid as catalyst. On the other hand, a steroid-acetamide derivative (compound 7) was synthesized by the reaction of 6 with chloroacetyl chloride in the presence of triethylamine. Finally, the compound 7 was reacted with 2-hydroxy-1-naphthaldehyde in basic medium to form a steroid-oxirane carboxamide derivative (compound 8). The structure of all compounds obtained was confirmed by spectroscopic and spectrometric methods.
KW - Estradiol
KW - Steroid-dicarbaldehyde derivative
KW - Synthesis
KW - Three-component system
UR - http://www.scopus.com/inward/record.url?scp=84961132689&partnerID=8YFLogxK
U2 - 10.2174/1570178612666150910222245
DO - 10.2174/1570178612666150910222245
M3 - Artículo
SN - 1570-1786
VL - 12
SP - 699
EP - 707
JO - Letters in Organic Chemistry
JF - Letters in Organic Chemistry
IS - 10
ER -