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3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L
The title compound, C(11)H(13)N(2)O(+)·Cl(−)·2H(2)O, the dihydrate of (+)-vasicinol hydrochloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position...
Autores principales: | , , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968537/ https://www.ncbi.nlm.nih.gov/pubmed/21582144 http://dx.doi.org/10.1107/S1600536809003766 |
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author | Khan, Amir Muhammad Abbas, Ghulam Qureshi, Rizwana Aleem Khan, Uzma Ghufran, Muhammad Asad Stoeckli-Evans, Helen |
author_facet | Khan, Amir Muhammad Abbas, Ghulam Qureshi, Rizwana Aleem Khan, Uzma Ghufran, Muhammad Asad Stoeckli-Evans, Helen |
author_sort | Khan, Amir Muhammad |
collection | PubMed |
description | The title compound, C(11)H(13)N(2)O(+)·Cl(−)·2H(2)O, the dihydrate of (+)-vasicinol hydrochloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position 2 acting as the flap and the C atom at position 3, carrying the hydroxyl substituent, has an S configuration. The absolute configuration was determined as a result of the anomalous scattering of the Cl atom. In the crystal structure, molecules stack along the a axis, connected to one another via intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming approximately triangular-shaped R (2) (1)(7) rings, and O—H⋯Cl and O—H⋯O hydrogen bonds, forming pentagonal-shaped R (5) (4)(10) rings. The overall effect is a ribbon-like arrangement running parallel to the a axis. |
format | Text |
id | pubmed-2968537 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29685372010-12-30 3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L Khan, Amir Muhammad Abbas, Ghulam Qureshi, Rizwana Aleem Khan, Uzma Ghufran, Muhammad Asad Stoeckli-Evans, Helen Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(11)H(13)N(2)O(+)·Cl(−)·2H(2)O, the dihydrate of (+)-vasicinol hydrochloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position 2 acting as the flap and the C atom at position 3, carrying the hydroxyl substituent, has an S configuration. The absolute configuration was determined as a result of the anomalous scattering of the Cl atom. In the crystal structure, molecules stack along the a axis, connected to one another via intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming approximately triangular-shaped R (2) (1)(7) rings, and O—H⋯Cl and O—H⋯O hydrogen bonds, forming pentagonal-shaped R (5) (4)(10) rings. The overall effect is a ribbon-like arrangement running parallel to the a axis. International Union of Crystallography 2009-02-06 /pmc/articles/PMC2968537/ /pubmed/21582144 http://dx.doi.org/10.1107/S1600536809003766 Text en © Khan et al. 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 Khan, Amir Muhammad Abbas, Ghulam Qureshi, Rizwana Aleem Khan, Uzma Ghufran, Muhammad Asad Stoeckli-Evans, Helen 3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L |
title | 3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L |
title_full | 3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L |
title_fullStr | 3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L |
title_full_unstemmed | 3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L |
title_short | 3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from Peganum harmala L |
title_sort | 3-hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydrochloride dihydrate from peganum harmala l |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968537/ https://www.ncbi.nlm.nih.gov/pubmed/21582144 http://dx.doi.org/10.1107/S1600536809003766 |
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