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- Title
Bio-Oriented Synthesis and Molecular Docking Studies of 1,2,4-Triazole Based Derivatives as Potential Anti-Cancer Agents against HepG2 Cell Line.
- Authors
Akhter, Naheed; Batool, Sidra; Khan, Samreen Gul; Rasool, Nasir; Anjum, Fozia; Rasul, Azhar; Adem, Şevki; Mahmood, Sadaf; Rehman, Aziz ur; Nisa, Mehr un; Razzaq, Zainib; Christensen, Jørn B.; Abourehab, Mohammed A. S.; Shah, Syed Adnan Ali; Imran, Syahrul
- Abstract
Triazole-based acetamides serve as important scaffolds for various pharmacologically active drugs. In the present work, structural hybrids of 1,2,4-triazole and acetamides were furnished by chemically modifying 2-(4-isobutylphenyl) propanoic acid (1). Target compounds 7a–f were produced in considerable yields (70–76%) by coupling the triazole of compound 1 with different electrophiles under different reaction conditions. These triazole-coupled acetamide derivatives were verified by physiochemical and spectroscopic (HRMS, FTIR, 13CNMR, and 1HNMR,) methods. The anti-liver carcinoma effects of all of the derivatives against a HepG2 cell line were investigated. Compound 7f, with two methyl moieties at the ortho-position, exhibited the highest anti-proliferative activity among all of the compounds with an IC50 value of 16.782 µg/mL. 7f, the most effective anti-cancer molecule, also had a very low toxicity of 1.190.02%. Molecular docking demonstrates that all of the compounds, especially 7f, have exhibited excellent binding affinities of −176.749 kcal/mol and −170.066 kcal/mol to c-kit tyrosine kinase and protein kinase B, respectively. Compound 7f is recognized as the most suitable drug pharmacophore for the treatment of hepatocellular carcinoma.
- Subjects
MOLECULAR docking; TRIAZOLE derivatives; ANTINEOPLASTIC agents; PROTEIN kinase B; CELL lines; ACETAMIDE
- Publication
Pharmaceuticals (14248247), 2023, Vol 16, Issue 2, p211
- ISSN
1424-8247
- Publication type
Academic Journal
- DOI
10.3390/ph16020211