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- Title
Synthesis and Antiproliferative Activities of Benzimidazole-Based Sulfide and Sulfoxide Derivatives.
- Authors
GABALLAH, Samir T.; EL-NEZHAWY, Ahmed O. H.; AMER, HASSAN; ALI, Mamdouh Moawad; El-Din MAHMOUD, Abeer Essam; HOFINGER-HORVATH, Andreas
- Abstract
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 structureactivity 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 IC50 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.
- Subjects
SULFIDE synthesis; SULFOXIDES synthesis; BENZIMIDAZOLE derivatives; CHEMOSELECTIVITY; PROSTATE cancer treatment; DOXORUBICIN
- Publication
Scientia Pharmaceutica, 2016, Vol 84, Issue 1, p1
- ISSN
0036-8709
- Publication type
Article
- DOI
10.3797/scipharm.1507-02