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Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate
The title compound, C(33)H(49)NO(3), is the propargylamide of 18β-glycyrrhetinic acid, a pentacyclic triterpenoid of interest as a therapeutic agent. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ri...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247445/ https://www.ncbi.nlm.nih.gov/pubmed/22220063 http://dx.doi.org/10.1107/S1600536811043534 |
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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(33)H(49)NO(3), is the propargylamide of 18β-glycyrrhetinic acid, a pentacyclic triterpenoid of interest as a therapeutic agent. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring C in a half-chair conformation. In the crystal, the terminal N-propargylcarboxamide group has remarkable structural effects on weak hydrogen-bond-like interactions. Particularly noteworthy are an intermolecular O—H⋯π interaction accepted side-on by the terminal alkyne group [O⋯C = 3.097 (2) and 3.356 (2) Å] and a short intermolecular C—H⋯O interaction [C⋯O = 3.115 (2) Å] donated by the alkyne C—H group. An N—H⋯O [N⋯O = 3.251 (2) Å] and a C(alkyl)—H⋯O [C⋯O = 3.254 (2) Å] interaction complement the crystal structure. |
format | Online Article Text |
id | pubmed-3247445 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32474452012-01-04 Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate Czollner, Laszlo Jordis, Ulrich Mereiter, Kurt Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(33)H(49)NO(3), is the propargylamide of 18β-glycyrrhetinic acid, a pentacyclic triterpenoid of interest as a therapeutic agent. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring C in a half-chair conformation. In the crystal, the terminal N-propargylcarboxamide group has remarkable structural effects on weak hydrogen-bond-like interactions. Particularly noteworthy are an intermolecular O—H⋯π interaction accepted side-on by the terminal alkyne group [O⋯C = 3.097 (2) and 3.356 (2) Å] and a short intermolecular C—H⋯O interaction [C⋯O = 3.115 (2) Å] donated by the alkyne C—H group. An N—H⋯O [N⋯O = 3.251 (2) Å] and a C(alkyl)—H⋯O [C⋯O = 3.254 (2) Å] interaction complement the crystal structure. International Union of Crystallography 2011-10-29 /pmc/articles/PMC3247445/ /pubmed/22220063 http://dx.doi.org/10.1107/S1600536811043534 Text en © Czollner et al. 2011 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 Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate |
title | Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate |
title_full | Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate |
title_fullStr | Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate |
title_full_unstemmed | Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate |
title_short | Propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate |
title_sort | propargylaminyl 3α-hydroxy-11-oxo-18β-olean-12-en-29-oate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247445/ https://www.ncbi.nlm.nih.gov/pubmed/22220063 http://dx.doi.org/10.1107/S1600536811043534 |
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