TY - JOUR
T1 - Design and synthesis of four steroid-oxirane derivatives using some chemical tools
AU - Lauro, Figueroa Valverde
AU - Francisco, Díaz Cedillo
AU - Otto, Ortega Morales
AU - Elodia, García Cervera
AU - Marcela, Rosas Nexticapa
AU - Eduardo, Pool Gómez
AU - Maria, Lopéz Ramos
AU - Fernanda, Rodriguez Hurtado
AU - Marissa, Chan Salvador
N1 - Publisher Copyright:
© 2016 Elsevier Inc. All rights reserved.
PY - 2016/8
Y1 - 2016/8
N2 - This study involved the synthesis of several new derivatives of progesterone, 11a-hydroxyprogesterone, 11a-t-butyldimethylsilanyloxyprogesterone, and andrenosterone. The new derivatives were prepared by condensation of the 4-en-3-one moiety of the four steroids with 2-hydroxy-1-naphthaldehyde to afford a series of 4-(R)-hydroxy-(2-hydroxynaphtalen-1-yl) adducts. These adducts were further modified by cyclization reactions of the dihydroxynaphthalenyl moieties with succinic acid, and the resulting cyclic succinates were then condensed with ethylenediamine to form imine derivatives at all available carbonyl groups. These compounds were then derivatized by N-acylation of the 11- and 17-imine nitrogens with chloroacetyl chloride and the resulting chloroacetamides were then condensed with 2-hydroxy-1-napthaldehyde in Darzens-type reactions forming the corresponding epoxy acetamides in the side chains. In addition, the chemical structure of steroid derivatives was confirmed by NMR spectroscopic data.
AB - This study involved the synthesis of several new derivatives of progesterone, 11a-hydroxyprogesterone, 11a-t-butyldimethylsilanyloxyprogesterone, and andrenosterone. The new derivatives were prepared by condensation of the 4-en-3-one moiety of the four steroids with 2-hydroxy-1-naphthaldehyde to afford a series of 4-(R)-hydroxy-(2-hydroxynaphtalen-1-yl) adducts. These adducts were further modified by cyclization reactions of the dihydroxynaphthalenyl moieties with succinic acid, and the resulting cyclic succinates were then condensed with ethylenediamine to form imine derivatives at all available carbonyl groups. These compounds were then derivatized by N-acylation of the 11- and 17-imine nitrogens with chloroacetyl chloride and the resulting chloroacetamides were then condensed with 2-hydroxy-1-napthaldehyde in Darzens-type reactions forming the corresponding epoxy acetamides in the side chains. In addition, the chemical structure of steroid derivatives was confirmed by NMR spectroscopic data.
KW - Chloroacetyl chloride
KW - Oxirane ring
KW - Progesterone
KW - Steroid derivatives
UR - http://www.scopus.com/inward/record.url?scp=84969507023&partnerID=8YFLogxK
U2 - 10.1016/j.steroids.2016.04.012
DO - 10.1016/j.steroids.2016.04.012
M3 - Artículo
SN - 0039-128X
VL - 112
SP - 20
EP - 35
JO - Steroids
JF - Steroids
ER -