Synthesis of Ninhydrin Derivatives and their Anticancer, Antimicrobial and Cholinesterase Enzymes Inhibitory Activities

2-Chloro-1,3-dioxo-2,3-dihydro-1H-inden-2-yl acetate (1) and N11,N11'-benzene-1“,2”-diamino-11H,11'H- [11,11'-biindeno[1,2-b]quinoxaline] (2) were synthesized and structures have been established on the basis of spectral analysis. The structure of (2) has also been confirmed by single crystal X-ray analysis. Both the synthesized compounds were screened for their anticancer, antimicrobial and cholinesterase enzymes inhibitory activities. Compound (2) showed good anticancer and antibacterial activities. Both 1 and 2 showed good anticandida activity comparable to that of clinically used antifungal agent, amphotericin B. These compounds were found to have contrasting cholinesterase enzymes inhibitory activities. Compound 1 showed highly selective inhibitory activity against butyrylcholinesterase enzyme whereas 2 was more selective inhibitor of acetylcholinesterase with moderate inhibitory activity against butyrylcholinesterase. Structural modification of 1 to 2 has major implication on their antimicrobial and cholinesterase enzymes inhibitory bioactivities.