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(1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum

The title compound, C(29)H(37)NO(6), was isolated from Aconitum zeravschanicum and exhibits anti­arhythmic activity. It is a derivative of the diterpenoid alkaloid heteratisine and as such the core framework of the mol­ecule contains four six-membered, three seven-membered and one five-membered ring...

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Detalles Bibliográficos
Autores principales: Tashkhodjaev, Bakhodir, Salimov, Bakhodir T.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969503/
https://www.ncbi.nlm.nih.gov/pubmed/21582940
http://dx.doi.org/10.1107/S1600536809023873
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author Tashkhodjaev, Bakhodir
Salimov, Bakhodir T.
author_facet Tashkhodjaev, Bakhodir
Salimov, Bakhodir T.
author_sort Tashkhodjaev, Bakhodir
collection PubMed
description The title compound, C(29)H(37)NO(6), was isolated from Aconitum zeravschanicum and exhibits anti­arhythmic activity. It is a derivative of the diterpenoid alkaloid heteratisine and as such the core framework of the mol­ecule contains four six-membered, three seven-membered and one five-membered ring. The chair conformation of one of the meth­oxy-substituted six-membered rings is different from that observed in heteratisine hydro­bromide monohydrate. In the latter case, this ring adopts a boat conformation due to a stabilizing intra­molecular N—H⋯O hydrogen bond. In the crystal structure of the title compound, there is only one acidic H atom. This hydroxyl group forms an inter­molecular O—H⋯O hydrogen bond that links mol­ecules into infinite chains along the b axis.
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spelling pubmed-29695032010-12-30 (1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum Tashkhodjaev, Bakhodir Salimov, Bakhodir T. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(29)H(37)NO(6), was isolated from Aconitum zeravschanicum and exhibits anti­arhythmic activity. It is a derivative of the diterpenoid alkaloid heteratisine and as such the core framework of the mol­ecule contains four six-membered, three seven-membered and one five-membered ring. The chair conformation of one of the meth­oxy-substituted six-membered rings is different from that observed in heteratisine hydro­bromide monohydrate. In the latter case, this ring adopts a boat conformation due to a stabilizing intra­molecular N—H⋯O hydrogen bond. In the crystal structure of the title compound, there is only one acidic H atom. This hydroxyl group forms an inter­molecular O—H⋯O hydrogen bond that links mol­ecules into infinite chains along the b axis. International Union of Crystallography 2009-06-27 /pmc/articles/PMC2969503/ /pubmed/21582940 http://dx.doi.org/10.1107/S1600536809023873 Text en © Tashkhodjaev and Salimov 2009 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
Tashkhodjaev, Bakhodir
Salimov, Bakhodir T.
(1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum
title (1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum
title_full (1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum
title_fullStr (1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum
title_full_unstemmed (1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum
title_short (1α,8β)-6β-Benzo­yloxy-6-dehydroxy­heteratisine from Aconitum zeravschanicum
title_sort (1α,8β)-6β-benzo­yloxy-6-dehydroxy­heteratisine from aconitum zeravschanicum
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969503/
https://www.ncbi.nlm.nih.gov/pubmed/21582940
http://dx.doi.org/10.1107/S1600536809023873
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