Bio-Oriented Synthesis and Molecular Docking Studies of 1,2,4-Triazole Based Derivatives as Potential Anti-Cancer Agents against HepG2 Cell Line

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 ( ). Target compounds were produced in considerable y...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Pharmaceuticals (Basel, Switzerland) Switzerland), 2023-01, Vol.16 (2), p.211
Hauptverfasser: 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
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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 ( ). Target compounds 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, CNMR, and HNMR,) methods. The anti-liver carcinoma effects of all of the derivatives against a HepG2 cell line were investigated. Compound , with two methyl moieties at the ortho-position, exhibited the highest anti-proliferative activity among all of the compounds with an IC value of 16.782 µg/mL. , 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 , 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 is recognized as the most suitable drug pharmacophore for the treatment of hepatocellular carcinoma.
ISSN:1424-8247
1424-8247
DOI:10.3390/ph16020211