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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-...

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Autores principales: Tojiboev, Akmal, Zhurakulov, Sherzod, Vinogradova, Valentina, Englert, Ulli, Wang, Ruimin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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.
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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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