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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...

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Autores principales: Touj, Nedra, Al-Ayed, Abdullah S., Sauthier, Mathieu, Mansour, Lamjed, Harrath, Abdel Halim, Al-Tamimi, Jamil, Özdemir, Ismail, Yaşar, Sedat, Hamdi, Naceur
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
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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.
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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
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