Herein, we report the synthesis and biopharmaceutical characterization of coumarin based azo compounds. The novel coumarin based azo compounds were obtained by the coupling of bis-coumarin (2Z,20 Z)-2, 20 -[ethane-1,2-diylbis(azan-1-yl-1-ylidene)]bis(4-methylchroman-7-ol) with diazotized aromatic amines. The compounds were fully characterized using spectroscopic analytical method and tested for their antibacterial and antifungal activity. A correlation of structure and activities relationship of these compounds with respect to molecular modeling, Lipinski rule of five, drug-likeness, toxicity profiles, and other physico-chemical properties of drugs are described and verified experimentally.