Cargando…
Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives
The design, synthesis, and in vitro antiproliferative activity of a novel series of sulfide (4a–i) and sulfoxide (5a–h) derivatives of benzimidazole, in which different aromatic and heteroaromatic acetamides are linked to benzimidazole via sulfide (4a–i) and sulfoxide (5a–h) linker, are reported and...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Austrian Journal of Pharmaceutical Sciences
2016
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4839274/ https://www.ncbi.nlm.nih.gov/pubmed/27110495 http://dx.doi.org/10.3797/scipharm.1507-02 |
_version_ | 1782428122539360256 |
---|---|
author | Gaballah, Samir T. El-Nezhawy, Ahmed O. H. Amer, Hassan Ali, Mamdouh Moawad Mahmoud, Abeer Essam El-Din Hofinger-Horvath, Andreas |
author_facet | Gaballah, Samir T. El-Nezhawy, Ahmed O. H. Amer, Hassan Ali, Mamdouh Moawad Mahmoud, Abeer Essam El-Din Hofinger-Horvath, Andreas |
author_sort | Gaballah, Samir T. |
collection | PubMed |
description | The design, synthesis, and in vitro antiproliferative activity of a novel series of sulfide (4a–i) and sulfoxide (5a–h) derivatives of benzimidazole, in which different aromatic and heteroaromatic acetamides are linked to benzimidazole via sulfide (4a–i) and sulfoxide (5a–h) linker, are reported and the structure-activity relationship is discussed. The new derivatives were prepared by coupling 2-(mercaptomethyl)benzimidazole with 2-bromo-N-(substituted) acetamides in dry acetone in the presence of anhydrous potassium carbonate. With very few exceptions, all of the synthesized compounds showed varying antiprolific activities against HepG2, MCF-7, and A549 cell lines. Compound 5a was very similar in potency to doxorubicin as an anticancer drug, with IC(50) values 4.1 ± 0.5, 4.1 ± 0.5, and 5.0 ± 0.6 µg/mL versus 4.2 ± 0.5, 4.9 ± 0.6, and 6.1 ± 0.6 µg/mL against HepG2, MCF-7, and A549 cell lines, respectively. In contrast, none of the compounds showed activity against human prostate PC3 cancer cells. Additionally, the sulfoxide derivatives were more potent than the corresponding sulfides. |
format | Online Article Text |
id | pubmed-4839274 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | The Austrian Journal of Pharmaceutical Sciences |
record_format | MEDLINE/PubMed |
spelling | pubmed-48392742016-04-22 Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives Gaballah, Samir T. El-Nezhawy, Ahmed O. H. Amer, Hassan Ali, Mamdouh Moawad Mahmoud, Abeer Essam El-Din Hofinger-Horvath, Andreas Sci Pharm Research Article The design, synthesis, and in vitro antiproliferative activity of a novel series of sulfide (4a–i) and sulfoxide (5a–h) derivatives of benzimidazole, in which different aromatic and heteroaromatic acetamides are linked to benzimidazole via sulfide (4a–i) and sulfoxide (5a–h) linker, are reported and the structure-activity relationship is discussed. The new derivatives were prepared by coupling 2-(mercaptomethyl)benzimidazole with 2-bromo-N-(substituted) acetamides in dry acetone in the presence of anhydrous potassium carbonate. With very few exceptions, all of the synthesized compounds showed varying antiprolific activities against HepG2, MCF-7, and A549 cell lines. Compound 5a was very similar in potency to doxorubicin as an anticancer drug, with IC(50) values 4.1 ± 0.5, 4.1 ± 0.5, and 5.0 ± 0.6 µg/mL versus 4.2 ± 0.5, 4.9 ± 0.6, and 6.1 ± 0.6 µg/mL against HepG2, MCF-7, and A549 cell lines, respectively. In contrast, none of the compounds showed activity against human prostate PC3 cancer cells. Additionally, the sulfoxide derivatives were more potent than the corresponding sulfides. The Austrian Journal of Pharmaceutical Sciences 2016 2015-08-18 /pmc/articles/PMC4839274/ /pubmed/27110495 http://dx.doi.org/10.3797/scipharm.1507-02 Text en Copyright: © Gaballah et al. http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Article Gaballah, Samir T. El-Nezhawy, Ahmed O. H. Amer, Hassan Ali, Mamdouh Moawad Mahmoud, Abeer Essam El-Din Hofinger-Horvath, Andreas Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives |
title | Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives |
title_full | Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives |
title_fullStr | Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives |
title_full_unstemmed | Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives |
title_short | Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives |
title_sort | synthesis and antiproliferative activities of benzimidazole-based sulfide and sulfoxide derivatives |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4839274/ https://www.ncbi.nlm.nih.gov/pubmed/27110495 http://dx.doi.org/10.3797/scipharm.1507-02 |
work_keys_str_mv | AT gaballahsamirt synthesisandantiproliferativeactivitiesofbenzimidazolebasedsulfideandsulfoxidederivatives AT elnezhawyahmedoh synthesisandantiproliferativeactivitiesofbenzimidazolebasedsulfideandsulfoxidederivatives AT amerhassan synthesisandantiproliferativeactivitiesofbenzimidazolebasedsulfideandsulfoxidederivatives AT alimamdouhmoawad synthesisandantiproliferativeactivitiesofbenzimidazolebasedsulfideandsulfoxidederivatives AT mahmoudabeeressameldin synthesisandantiproliferativeactivitiesofbenzimidazolebasedsulfideandsulfoxidederivatives AT hofingerhorvathandreas synthesisandantiproliferativeactivitiesofbenzimidazolebasedsulfideandsulfoxidederivatives |