Novel N-Alkyl-4-(6-fluoro-1H-indol-3-yl)benzamide Derivatives as Anticancer Agents: Design, Synthesis,Biological Evaluation, and Molecular Docking Study

A number of novel N-alkyl-4-(6-fluoro-1H-indol-3-yl)benzamide derivatives were synthesized and characterized with modern spectroscopic techniques (NMR, IR, and MS). The synthesized compounds were assessed for their cytotoxic activities against two cancer cell lines, namely HeLa (cervical cancer) and MCF-7 (breast cancer), by MTT assay. The results showed that the compounds with 3-fluorobenzyl, 4-fluorobenzyl, 4-(trifluoromethyl)benzyl, and 4-(diethylamino)butan-2-yl substituents on the amide nitrogen atom possess potent activity against both cancer cell lines. The N-[4-(diethylamino)butan-2-yl]benzamide derivative showed potential cytotoxic action on HeLa and MCF-7 cell lines with IC50 values of 16.07 and 15.84 μg/mL, respectively, which are comparable with those of the standard drug doxorubicin. Molecular docking study of these four compounds also showed strong binding activity through hydrophobic interactions with Pin1 protein (PDBID: 2XPB).