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Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivative...

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Autores principales: Bandaru, Siva Sankar Murthy, Dzubiel, Darinka, Ihmels, Heiko, Karbasiyoun, Mohebodin, Mahmoud, Mohamed M A, Schulzke, Carola
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071731/
https://www.ncbi.nlm.nih.gov/pubmed/30112092
http://dx.doi.org/10.3762/bjoc.14.161
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author Bandaru, Siva Sankar Murthy
Dzubiel, Darinka
Ihmels, Heiko
Karbasiyoun, Mohebodin
Mahmoud, Mohamed M A
Schulzke, Carola
author_facet Bandaru, Siva Sankar Murthy
Dzubiel, Darinka
Ihmels, Heiko
Karbasiyoun, Mohebodin
Mahmoud, Mohamed M A
Schulzke, Carola
author_sort Bandaru, Siva Sankar Murthy
collection PubMed
description 9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants of K(b) = 0.2–2.2 × 10(5) M(−1).
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spelling pubmed-60717312018-08-15 Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions Bandaru, Siva Sankar Murthy Dzubiel, Darinka Ihmels, Heiko Karbasiyoun, Mohebodin Mahmoud, Mohamed M A Schulzke, Carola Beilstein J Org Chem Full Research Paper 9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants of K(b) = 0.2–2.2 × 10(5) M(−1). Beilstein-Institut 2018-07-23 /pmc/articles/PMC6071731/ /pubmed/30112092 http://dx.doi.org/10.3762/bjoc.14.161 Text en Copyright © 2018, Bandaru et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Bandaru, Siva Sankar Murthy
Dzubiel, Darinka
Ihmels, Heiko
Karbasiyoun, Mohebodin
Mahmoud, Mohamed M A
Schulzke, Carola
Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions
title Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions
title_full Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions
title_fullStr Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions
title_full_unstemmed Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions
title_short Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions
title_sort synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by palladium-mediated cross-coupling reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071731/
https://www.ncbi.nlm.nih.gov/pubmed/30112092
http://dx.doi.org/10.3762/bjoc.14.161
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