Synthesis and Biological Evaluation of Aminonaphthols Incorporated Indole Derivatives

Abstract

An efficient one pot condensation of naphthols (1), 2,5-disubstituted indole-3-carboxaldehydes (2), and secondary amines (3) has been achieved using dichloromethane as a solvent, stirring at room temperature. Some of the new [(disubstituted amino)(5-substituted 2-phenyl-1 H -indol-3-yl)methyl]naphthalene-ols (4) derivatives were prepared in good yields. The significant features of this method are simple work-up procedure, inexpensive nontoxic solvent, shorter reaction times, and excellent product yields. The structures of newly synthesized compounds ( 4a–r ) are confirmed by their elemental analysis, FTIR, 1 H and 13 C NMR, and mass spectral data. These compounds were screened for their in vitro antioxidant, antimicrobial, antitubercular, and anticancer activities. Among the synthesized compounds ( 4a–r ), the compound 4e exhibited highest activity for radical scavenging and ferric ions reducing antioxidant power activities; compounds 4b , 4h , and 4k showed good metal chelating activity. Compounds 4n and 4q showed excellent antimicrobial activities with MIC value 08 µ g/mL against tested strains. Compounds 4h , 4k , 4n , and 4q exhibited promising antitubercular activity with MIC value 12.5 µ g/mL. Compounds 4k and 4q exhibited 100% cell lysis at concentration 10 µ g/mL against MDA-MB-231 (human adenocarcinoma mammary gland) cell lines.