Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate

The title compound, C(27)H(24)N(4)O(5), is an inter­mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo­addition. An intra­molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065 (6) Å] for the...

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Detalles Bibliográficos
Autores principales: Nissen, Felix, Schollmeyer, Dieter, Detert, Heiner
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120419/
https://www.ncbi.nlm.nih.gov/pubmed/21754865
http://dx.doi.org/10.1107/S1600536811018794
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author Nissen, Felix
Schollmeyer, Dieter
Detert, Heiner
author_facet Nissen, Felix
Schollmeyer, Dieter
Detert, Heiner
author_sort Nissen, Felix
collection PubMed
description The title compound, C(27)H(24)N(4)O(5), is an inter­mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo­addition. An intra­molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065 (6) Å] for the two rigid units. This hydrogen-bond-stabilized coplanarity has a very close analogy in the structure of the anti­tumor anti­biotic streptonigrin in the solid state and in solution. Inter­molecular hydrogen-bond bridges of amides groups along the a axis and π–π stacking inter­actions [centroid–centroid distance = 3.665 (9) Å] connect mol­ecules arranged in a parallel manner.
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spelling pubmed-31204192011-07-13 Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate Nissen, Felix Schollmeyer, Dieter Detert, Heiner Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(27)H(24)N(4)O(5), is an inter­mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo­addition. An intra­molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065 (6) Å] for the two rigid units. This hydrogen-bond-stabilized coplanarity has a very close analogy in the structure of the anti­tumor anti­biotic streptonigrin in the solid state and in solution. Inter­molecular hydrogen-bond bridges of amides groups along the a axis and π–π stacking inter­actions [centroid–centroid distance = 3.665 (9) Å] connect mol­ecules arranged in a parallel manner. International Union of Crystallography 2011-05-25 /pmc/articles/PMC3120419/ /pubmed/21754865 http://dx.doi.org/10.1107/S1600536811018794 Text en © Nissen 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
Nissen, Felix
Schollmeyer, Dieter
Detert, Heiner
Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate
title Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate
title_full Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate
title_fullStr Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate
title_full_unstemmed Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate
title_short Methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate
title_sort methyl 1-(7-acetamido-5,8-dimeth­oxy­quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120419/
https://www.ncbi.nlm.nih.gov/pubmed/21754865
http://dx.doi.org/10.1107/S1600536811018794
work_keys_str_mv AT nissenfelix methyl17acetamido58dimethoxyquinolin2yl4methylbcarboline3carboxylate
AT schollmeyerdieter methyl17acetamido58dimethoxyquinolin2yl4methylbcarboline3carboxylate
AT detertheiner methyl17acetamido58dimethoxyquinolin2yl4methylbcarboline3carboxylate

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