Synthesis, Molecular Docking and Evaluation of 1,3,4‐Oxadiazole‐Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents

Abstract

In drug discovery, the hybridization of bioactive pharmacophores is a powerful tool for targeting enzymes involved in cancer and microbial cell growth. A combination of 1,3,4‐oxadiazole and isobenzofuran may improve the antitumor and antimicrobial properties of the hybrid molecules. A series of hybrid molecules having 1,3,4‐oxadiazole and isobenzofuran were synthesized and structural characterization was done by FT‐IR, 1H‐NMR, 13C‐NMR, and mass spectrometry. Molecular docking studies were performed to investigate binding interactions of compounds with proteins (PDB NO: 2R3J and 1GII), and the results were consistent with in vitro anticancer data. All the synthesized compounds were tested for antimicrobial activity against S. aureus, E. faecalis (Gram‐positive) and E. coli and P. aeruginosa (Gram‐negative) bacterial strains. Among the synthesized compounds, 7a and 7b displayed good activity against the tested bacterial strains. Also, compounds were tested for their anti‐tumor activity against breast cancer (MCF‐7) and colon cancer (HCT‐116) cell lines via SRB assay. In comparison to doxorubicin (1.14 μM), hybrids 7e (4.32 μM), 7f (4.15 μM), 7g (4.66 μM), and 7h (4.83 μM) demonstrated comparable IC50 value against the HCT 116 cell line.

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

“…Among the derivatives evaluated, compound 289 revealed highest activity with IC 50 value of 4.15 μM. [84]…”

“…The compounds show excellent anticancer activity against HCT 116 cell lines. Among the derivatives evaluated, compound 289 revealed highest activity with IC 50 value of 4.15 μM [84] …”

The anti‐breast cancer potential of indole/isatin hybrids

“…Further studies revealed that the incorporation of isobenzofuran or thioether between indole and 1,3,4-oxadiazole moieties could not improve the activity. [77,78]…”