Issue 9, 2024, Issue in Progress

Synthesis, computational chemical study, antiproliferative activity screening, and molecular docking of some thiophene-based oxadiazole, triazole, and thiazolidinone derivatives

Abstract

Thiophene-2-carbohydrazide was used in this study to produce some thiophene-containing oxadiazole, triazole, and thiazolidinone derivatives through reactions with various carbon-centered electrophiles. Besides, the hydrazone obtained was allowed to react with mercaptoacetic acid and acetic anhydride to construct thiazolidinone and oxadiazole derivatives. The results of computational chemical study and outcomes of the experiments were in good agreement. The in vitro antiproliferative activity of the produced compounds was examined against two human cell lines namely, breast adenocarcinoma (MCF7) and colon cancer (HCT116) cell lines using doxorubicin as a reference anticancer agent. The produced hydrazones and spiro-indolin-oxadiazole derivatives were the most potent against the two cancer cell lines. The molecular docking was conducted to demonstrate the binding energies of produced substances toward human carbonic anhydrase IX (CA IX) protein. The binding energies of these ligands were near to that of the co-crystallized ligand (9FK). Compound 11b exhibits a binding energy of −5.5817 kcal mol−1, indicating tight binding to some key nucleobases and amino acids of CA IX protein, while compound 11a displays a higher binding energy compared to the reference ligand (9FK). This suggests that compounds 11b and 11a display a notably strong binding affinity towards the human carbonic anhydrase IX (CA IX) protein. ADME profiles of the potent compounds including physicochemical characteristics, lipophilicity, and drug-likeness were predicted.

Graphical abstract: Synthesis, computational chemical study, antiproliferative activity screening, and molecular docking of some thiophene-based oxadiazole, triazole, and thiazolidinone derivatives

Supplementary files

Article information

Article type
Paper
Submitted
16 Oct 2023
Accepted
07 Feb 2024
First published
15 Feb 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 5926-5940

Synthesis, computational chemical study, antiproliferative activity screening, and molecular docking of some thiophene-based oxadiazole, triazole, and thiazolidinone derivatives

A. S. Elgubbi, E. A. E. El-Helw, A. Y. A. Alzahrani and S. K. Ramadan, RSC Adv., 2024, 14, 5926 DOI: 10.1039/D3RA07048D

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