Design and synthesis of four steroid-oxirane derivatives using some chemical tools

Figueroa Valverde Lauro, Díaz Cedillo Francisco, Ortega Morales Otto, García Cervera Elodia, Rosas Nexticapa Marcela, Pool Gómez Eduardo, Lopéz Ramos Maria, Rodriguez Hurtado Fernanda, Chan Salvador Marissa

Research output: Contribution to journalArticle

Abstract

© 2016 Elsevier Inc. All rights reserved. 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.
Original languageAmerican English
Pages (from-to)20-35
Number of pages16
JournalSteroids
DOIs
StatePublished - 1 Aug 2016

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Ethylene Oxide
ethylenediamine
Imines
Acetamides
Succinates
Steroids
Hydroxyprogesterones
Derivatives
Acylation
Succinic Acid
Cyclization
Progesterone
Nitrogen
Condensation
Nuclear magnetic resonance
chloroacetamide
chloroacetyl chloride
2-hydroxy-1-naphthaldehyde

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Lauro, F. V., Francisco, D. C., Otto, O. M., Elodia, G. C., Marcela, R. N., Eduardo, P. G., ... Marissa, C. S. (2016). Design and synthesis of four steroid-oxirane derivatives using some chemical tools. Steroids, 20-35. https://doi.org/10.1016/j.steroids.2016.04.012
Lauro, Figueroa Valverde ; Francisco, Díaz Cedillo ; Otto, Ortega Morales ; Elodia, García Cervera ; Marcela, Rosas Nexticapa ; Eduardo, Pool Gómez ; Maria, Lopéz Ramos ; Fernanda, Rodriguez Hurtado ; Marissa, Chan Salvador. / Design and synthesis of four steroid-oxirane derivatives using some chemical tools. In: Steroids. 2016 ; pp. 20-35.
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abstract = "{\circledC} 2016 Elsevier Inc. All rights reserved. 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.",
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Lauro, FV, Francisco, DC, Otto, OM, Elodia, GC, Marcela, RN, Eduardo, PG, Maria, LR, Fernanda, RH & Marissa, CS 2016, 'Design and synthesis of four steroid-oxirane derivatives using some chemical tools', Steroids, pp. 20-35. https://doi.org/10.1016/j.steroids.2016.04.012

Design and synthesis of four steroid-oxirane derivatives using some chemical tools. / Lauro, Figueroa Valverde; Francisco, Díaz Cedillo; Otto, Ortega Morales; Elodia, García Cervera; Marcela, Rosas Nexticapa; Eduardo, Pool Gómez; Maria, Lopéz Ramos; Fernanda, Rodriguez Hurtado; Marissa, Chan Salvador.

In: Steroids, 01.08.2016, p. 20-35.

Research output: Contribution to journalArticle

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AU - Marcela, Rosas Nexticapa

AU - Eduardo, Pool Gómez

AU - Maria, Lopéz Ramos

AU - Fernanda, Rodriguez Hurtado

AU - Marissa, Chan Salvador

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Y1 - 2016/8/1

N2 - © 2016 Elsevier Inc. All rights reserved. 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 - © 2016 Elsevier Inc. All rights reserved. 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.

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