Synthesis, in silico ADME, molecular docking and in vitro cytotoxicity evaluation of stilbene linked 1,2,3-triazoles

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 triphenyl phosphonium halides 6a-f in benzene. The structures of the synthesized compounds were confirmed by FTIR, NMR (H-1 and C-13 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 mu M) 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.

Automated summary

A series of novel (E)-1-benzyl-4-((4-styrylphenoxy)methyl)-1H-1,2,3-triazole compounds were synthesized using Wittig reaction and evaluated for cytotoxicity. Some compounds exhibited moderate cytotoxicity against human cancer cell lines, while resveratrol linked compounds were more sensitive to leukemia and lymphoma cell lines.