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Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate
Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted isoquinoline, are coupled to give 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7273985/ https://www.ncbi.nlm.nih.gov/pubmed/32523763 http://dx.doi.org/10.1107/S2056989020006696 |
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author | Tojiboev, Akmal Zhurakulov, Sherzod Vinogradova, Valentina Englert, Ulli Wang, Ruimin |
author_facet | Tojiboev, Akmal Zhurakulov, Sherzod Vinogradova, Valentina Englert, Ulli Wang, Ruimin |
author_sort | Tojiboev, Akmal |
collection | PubMed |
description | Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted isoquinoline, are coupled to give 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one. The target product crystallizes as a methanol solvate, C(29)H(26)N(4)O(5)·CH(4)O, and is E configured. The alternative Z isomer would necessarily imply either considerable twist about the central double bond or very unfavourable intramolecular contacts between sterically more demanding substituents. The main residue and the co-crystallized solvent molecule aggregate to discrete pairs via a classical O—H⋯O hydrogen bond with a distance of 2.8581 (7) Å between the methanol OH donor and the quinazolinone O=C acceptor. |
format | Online Article Text |
id | pubmed-7273985 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-72739852020-06-09 Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate Tojiboev, Akmal Zhurakulov, Sherzod Vinogradova, Valentina Englert, Ulli Wang, Ruimin Acta Crystallogr E Crystallogr Commun Research Communications Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted isoquinoline, are coupled to give 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one. The target product crystallizes as a methanol solvate, C(29)H(26)N(4)O(5)·CH(4)O, and is E configured. The alternative Z isomer would necessarily imply either considerable twist about the central double bond or very unfavourable intramolecular contacts between sterically more demanding substituents. The main residue and the co-crystallized solvent molecule aggregate to discrete pairs via a classical O—H⋯O hydrogen bond with a distance of 2.8581 (7) Å between the methanol OH donor and the quinazolinone O=C acceptor. International Union of Crystallography 2020-05-22 /pmc/articles/PMC7273985/ /pubmed/32523763 http://dx.doi.org/10.1107/S2056989020006696 Text en © Tojiboev et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Tojiboev, Akmal Zhurakulov, Sherzod Vinogradova, Valentina Englert, Ulli Wang, Ruimin Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate |
title | Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate |
title_full | Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate |
title_fullStr | Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate |
title_full_unstemmed | Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate |
title_short | Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate |
title_sort | stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7273985/ https://www.ncbi.nlm.nih.gov/pubmed/32523763 http://dx.doi.org/10.1107/S2056989020006696 |
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