Synthesis optimization of a series of 2-amino acid-3-chloro-1,4-naphthoquinones demonstrated feasibility to conduct reactions in mild conditions providing relatively high yields, simple procedure and low time costs. Compounds were characterized with standard methods of chemical analysis and spectroscopic techniques. Physicochemical parameters of weight loss and start melting point were determined. Preliminary screening of synthesized compounds carried out with online based algorithm of prediction of activity spectra for synthesized substances (PASS).