Affiliation:
1. Islamic Azad University Science and Research Branch
2. Qom University of Medical Sciences and Health Services
3. Islamic Azad University of Qom
4. Qom University of Medical Sciences and Health Services School of Medicine
Abstract
Abstract
In this study, novel tetrazolic substituted para toluene sulfonamid derivatives were synthesized using an azide-nitrile cycloaddition reaction. The easy availability of the inexpensive starting materials, avoiding isolation and handling of hazardous organic azide, and mild reaction conditions make this synthetic protocol a valuable tool for the synthesis of functionalized tetrazole compounds. All reactions proceeded smoothly to achieve the corresponding tetrazole compounds 5a, in moderate to good yields (70–78%) using ZnBr2 as a catalyst and green solvent system H2O/2-propanol. The structure of all products was confirmed by FT-IR, 1HNMR, and 13CNMR analysis. N-((2H-tetrazol-5-yl)methyl)(phenyl)-N-tosylmethanamine and N-((2H-tetrazol-5-yl)methyl)-N-tosylpyridin-2-amine Cytotoxicity evaluations of compounds 5a and 5b on HT29 cell line demonstrated that compound 5a displayed the most potent in vitro antiproliferative activity with IC50 values of 85.57 ± 6.61 µM on HT29 cells. Although, compound 5b displayed anti-proliferative activity with IC50 values of 24.66 ± 4.51 µM on HT29 cells, comparable to Cisplatin, as a potent known anticancer drug with IC50 values of 7.49 ± 1.71 µM. Furthermore, we used molecular docking studies to investigate the possible drug-likeness of the synthesized molecules 5a, 5b revealing that some molecules are the most promising drug-like molecules out of the two synthesized molecules.
Publisher
Research Square Platform LLC