Cargando…
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...
Autores principales: | , , , , , |
---|---|
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 |
_version_ | 1783343919030861824 |
---|---|
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). |
format | Online Article Text |
id | pubmed-6071731 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT bandarusivasankarmurthy synthesisof9arylalkynyland9arylsubstitutedbenzobquinoliziniumderivativesbypalladiummediatedcrosscouplingreactions AT dzubieldarinka synthesisof9arylalkynyland9arylsubstitutedbenzobquinoliziniumderivativesbypalladiummediatedcrosscouplingreactions AT ihmelsheiko synthesisof9arylalkynyland9arylsubstitutedbenzobquinoliziniumderivativesbypalladiummediatedcrosscouplingreactions AT karbasiyounmohebodin synthesisof9arylalkynyland9arylsubstitutedbenzobquinoliziniumderivativesbypalladiummediatedcrosscouplingreactions AT mahmoudmohamedma synthesisof9arylalkynyland9arylsubstitutedbenzobquinoliziniumderivativesbypalladiummediatedcrosscouplingreactions AT schulzkecarola synthesisof9arylalkynyland9arylsubstitutedbenzobquinoliziniumderivativesbypalladiummediatedcrosscouplingreactions |