8-benzimidazolyl coumarin-3-oxadiazoles - Synthesis, docking studies and Anti-proliferative evaluation against breast cancer

A series of 8-benzimidazolyl-coumarin-3-oxadiazoles (10a-j) were synthesized and evaluated their anti-cancer activity against breast cancer using MCF-7 cell lines. Out of 10 tricore hybrids synthesized, the compound 10b with 2,4-dimethyl phenyl substitution on the oxadiazole ring is emerged as most potent compound with the IC50 value of 9.26 & mu;g/mL compared to the IC50 value of the standard drug doxorubicin 7.54 & mu;g/mL. The compound 10g with 2,6-difluoro phenyl substituted, 10c with 3-methoxy benzyl substituted and 10e with 4-chloro phenyl substitution on the oxadiazole ring are the other analogues with significant anti-cancer activity. The molecular docking studies using Autodock Vina tool revealed that the tested ligands have lower binding energy with the receptor protein quinone reductase-2 (PDB ID - 4ZVM) than the standard drug doxorubicin and exhibited similar amino acid interactions.

Automated summary

A series of 8-benzimidazolyl-coumarin-3-oxadiazoles were synthesized and evaluated for their anti-cancer activity against breast cancer. Compound 10b with 2,4-dimethyl phenyl substitution on the oxadiazole ring showed the highest potency with an IC50 value of 9.26 μg/mL compared to the standard drug doxorubicin. The compounds 10g, 10c, and 10e also showed significant anti-cancer activity and exhibited similar amino acid interactions as doxorubicin when docked with the receptor protein quinone reductase-2.