Cargando…
Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities
N,N-Substituted benzimidazole salts were successfully synthesized and characterized by (1)H-NMR, (13)C {(1)H} NMR and IR techniques, which support the proposed structures. Catalysts generated in situ were efficiently used for the carbonylative cross-coupling reaction of 2 bromopyridine with various...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2018
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9091359/ https://www.ncbi.nlm.nih.gov/pubmed/35558245 http://dx.doi.org/10.1039/c8ra08897g |
_version_ | 1784704903391739904 |
---|---|
author | Touj, Nedra Al-Ayed, Abdullah S. Sauthier, Mathieu Mansour, Lamjed Harrath, Abdel Halim Al-Tamimi, Jamil Özdemir, Ismail Yaşar, Sedat Hamdi, Naceur |
author_facet | Touj, Nedra Al-Ayed, Abdullah S. Sauthier, Mathieu Mansour, Lamjed Harrath, Abdel Halim Al-Tamimi, Jamil Özdemir, Ismail Yaşar, Sedat Hamdi, Naceur |
author_sort | Touj, Nedra |
collection | PubMed |
description | N,N-Substituted benzimidazole salts were successfully synthesized and characterized by (1)H-NMR, (13)C {(1)H} NMR and IR techniques, which support the proposed structures. Catalysts generated in situ were efficiently used for the carbonylative cross-coupling reaction of 2 bromopyridine with various boronic acids. The reaction was carried out in THF at 110 °C in the presence of K(2)CO(3) under inert conditions and yields unsymmetrical arylpyridine ketones. All N,N-substituted benzimidazole salts 2a–i and 4a–i studied in this work were screened for their cytotoxic activities against human cancer cell lines such us MDA-MB-231, MCF-7 and T47D. The N,N-substituted benzimidazoles 2e and 2f exhibited the most cytotoxic effect with promising cytotoxic activity with IC(50) values of 4.45 μg mL(−1) against MDA-MB-231 and 4.85 μg mL(−1) against MCF7 respectively. |
format | Online Article Text |
id | pubmed-9091359 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90913592022-05-11 Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities Touj, Nedra Al-Ayed, Abdullah S. Sauthier, Mathieu Mansour, Lamjed Harrath, Abdel Halim Al-Tamimi, Jamil Özdemir, Ismail Yaşar, Sedat Hamdi, Naceur RSC Adv Chemistry N,N-Substituted benzimidazole salts were successfully synthesized and characterized by (1)H-NMR, (13)C {(1)H} NMR and IR techniques, which support the proposed structures. Catalysts generated in situ were efficiently used for the carbonylative cross-coupling reaction of 2 bromopyridine with various boronic acids. The reaction was carried out in THF at 110 °C in the presence of K(2)CO(3) under inert conditions and yields unsymmetrical arylpyridine ketones. All N,N-substituted benzimidazole salts 2a–i and 4a–i studied in this work were screened for their cytotoxic activities against human cancer cell lines such us MDA-MB-231, MCF-7 and T47D. The N,N-substituted benzimidazoles 2e and 2f exhibited the most cytotoxic effect with promising cytotoxic activity with IC(50) values of 4.45 μg mL(−1) against MDA-MB-231 and 4.85 μg mL(−1) against MCF7 respectively. The Royal Society of Chemistry 2018-12-05 /pmc/articles/PMC9091359/ /pubmed/35558245 http://dx.doi.org/10.1039/c8ra08897g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Touj, Nedra Al-Ayed, Abdullah S. Sauthier, Mathieu Mansour, Lamjed Harrath, Abdel Halim Al-Tamimi, Jamil Özdemir, Ismail Yaşar, Sedat Hamdi, Naceur Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities |
title | Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities |
title_full | Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities |
title_fullStr | Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities |
title_full_unstemmed | Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities |
title_short | Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)(2) catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities |
title_sort | efficient in situ n-heterocyclic carbene palladium(ii) generated from pd(oac)(2) catalysts for carbonylative suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9091359/ https://www.ncbi.nlm.nih.gov/pubmed/35558245 http://dx.doi.org/10.1039/c8ra08897g |
work_keys_str_mv | AT toujnedra efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT alayedabdullahs efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT sauthiermathieu efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT mansourlamjed efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT harrathabdelhalim efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT altamimijamil efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT ozdemirismail efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT yasarsedat efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti AT hamdinaceur efficientinsitunheterocycliccarbenepalladiumiigeneratedfrompdoac2catalystsforcarbonylativesuzukicouplingreactionsofarylboronicacidswith2bromopyridineunderinertconditionsleadingtounsymmetricalarylpyridineketonessynthesischaracterizationandcytotoxicactiviti |