Synthesis, in silico ADME, molecular docking and in vitro cytotoxicity evaluation of stilbene linked 1,2,3-triazoles
Arnika Das,
Sujeet Kumar,
Leentje Persoons,
Dirk Daelemans,
Dominique Schols,
Hakan Alici,
Hakan Tahtaci,
Subhas S. Karki
Affiliations
Arnika Das
Department of Pharmaceutical Chemistry, KLE College of Pharmacy, Bengaluru, 560010, Karnataka, India; Dr Prabhakar B Kore Basic Science Research Centre, Off-Campus, KLE College of Pharmacy, A Constituent Unit of KLE Academy of Higher Education and Research-Belagavi, Bengaluru, 560010, Karnataka, India
Sujeet Kumar
Department of Pharmaceutical Chemistry, KLE College of Pharmacy, Bengaluru, 560010, Karnataka, India
Leentje Persoons
Rega Institute for Medical Research, Department of Microbiology, Immunology and Transplantation, Laboratory of Virology and Chemotherapy, KU Leuven, B-3000, Leuven, Belgium
Dirk Daelemans
Rega Institute for Medical Research, Department of Microbiology, Immunology and Transplantation, Laboratory of Virology and Chemotherapy, KU Leuven, B-3000, Leuven, Belgium
Dominique Schols
Rega Institute for Medical Research, Department of Microbiology, Immunology and Transplantation, Laboratory of Virology and Chemotherapy, KU Leuven, B-3000, Leuven, Belgium
Hakan Alici
Department of Physics, Faculty of Arts and Sciences, Zonguldak Bulent Ecevit University, 67100, Zonguldak, Turkey
Hakan Tahtaci
Department of Chemistry, Faculty of Science, Karabuk University, 78050, Karabuk, Turkey
Subhas S. Karki
Department of Pharmaceutical Chemistry, KLE College of Pharmacy, Bengaluru, 560010, Karnataka, India; Dr Prabhakar B Kore Basic Science Research Centre, Off-Campus, KLE College of Pharmacy, A Constituent Unit of KLE Academy of Higher Education and Research-Belagavi, Bengaluru, 560010, Karnataka, India; Corresponding author.
Series of (E)-1-benzyl-4-((4-styrylphenoxy)methyl)-1H-1,2,3-triazoles 7a-x were obtained by Wittig reaction between 4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehydes 5a-d and benzyl triphenylphosphonium halides 6a-f in benzene. The structures of the synthesized compounds were confirmed by FTIR, NMR (1H and 13C NMR) spectroscopy, and mass spectrometry. All synthesized compounds were screened for their cytotoxic activity against human cancer cell lines including pancreatic carcinoma, colorectal carcinoma, lung carcinoma, and leukemias such as acute lymphoblastic, chronic myeloid, and non-Hodgkinson lymphoma cell lines. In vitro cytotoxicity data showed that compounds 7c, 7e, 7h, 7j, 7k, 7r, and 7w were moderately cytotoxic (11.6–19.3 μM) against the selected cancer cell lines. These cytotoxicity findings were supported using molecular docking studies of the compounds against 1TUB receptor. The drug-likeness properties of the compounds evaluated by in silico ADME analyses. Resveratrol linked 1,2,3-triazoles were more sensitive towards human carcinoma cell lines but least sensitive towards leukemia and lymphoma cell lines.
