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(3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate

The title compound, C(34)H(52)N(2)O(7)·CH(4)O, is the methanol solvate of a difunctionalized derivative of the therapeutic agent 18β-glycyrrhetinic acid, a penta­cyclic triterpene. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conforma...

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Autores principales: Czollner, Laszlo, Jordis, Ulrich, Mereiter, Kurt
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344161/
https://www.ncbi.nlm.nih.gov/pubmed/22606164
http://dx.doi.org/10.1107/S1600536812012561
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author Czollner, Laszlo
Jordis, Ulrich
Mereiter, Kurt
author_facet Czollner, Laszlo
Jordis, Ulrich
Mereiter, Kurt
author_sort Czollner, Laszlo
collection PubMed
description The title compound, C(34)H(52)N(2)O(7)·CH(4)O, is the methanol solvate of a difunctionalized derivative of the therapeutic agent 18β-glycyrrhetinic acid, a penta­cyclic triterpene. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring in a half-chair conformation. This moiety is substituted by a nitrate ester group and an O-ethyl­glycine group. In the crystal, the nonsolvent mol­ecules are packed parallel to (010) in a herringbone fashion with the nitrato, ethyl­glycine and methanol-O atom being proximate. The methanol solvent mol­ecule is anchored via a donated O—H⋯O(ac­yl) and an accepted N—H⋯O hydrogen bond, giving rise to infinite zigzag chains of hydrogen bonds parallel to [100]. Two weak intermolecular C—H⋯O interactions to the methanol and to an acyl oxygen establish links along [100] and [010], respectively.
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spelling pubmed-33441612012-05-17 (3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate Czollner, Laszlo Jordis, Ulrich Mereiter, Kurt Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(34)H(52)N(2)O(7)·CH(4)O, is the methanol solvate of a difunctionalized derivative of the therapeutic agent 18β-glycyrrhetinic acid, a penta­cyclic triterpene. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring in a half-chair conformation. This moiety is substituted by a nitrate ester group and an O-ethyl­glycine group. In the crystal, the nonsolvent mol­ecules are packed parallel to (010) in a herringbone fashion with the nitrato, ethyl­glycine and methanol-O atom being proximate. The methanol solvent mol­ecule is anchored via a donated O—H⋯O(ac­yl) and an accepted N—H⋯O hydrogen bond, giving rise to infinite zigzag chains of hydrogen bonds parallel to [100]. Two weak intermolecular C—H⋯O interactions to the methanol and to an acyl oxygen establish links along [100] and [010], respectively. International Union of Crystallography 2012-03-31 /pmc/articles/PMC3344161/ /pubmed/22606164 http://dx.doi.org/10.1107/S1600536812012561 Text en © Czollner et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Czollner, Laszlo
Jordis, Ulrich
Mereiter, Kurt
(3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate
title (3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate
title_full (3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate
title_fullStr (3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate
title_full_unstemmed (3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate
title_short (3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate
title_sort (3β,18β,20β)-n-eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344161/
https://www.ncbi.nlm.nih.gov/pubmed/22606164
http://dx.doi.org/10.1107/S1600536812012561
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AT mereiterkurt 3b18b20bnethoxycarbonylmethyl3nitrato11oxoolean12ene29carboxamidemethanolmonosolvate