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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...

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Autores principales: Czollner, Laszlo, Jordis, Ulrich, Mereiter, Kurt
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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.
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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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