This research article reports the synthesis of 4,6-bis(5-aryl/heteroaryl-1,2-oxazol-3-yl)benzene-1,3-diol 4a–4f and 4,6-bis(5-aryl/heteroaryl-1H-pyrazol-3-yl)benzene-1,3-diol 5a–5f from 1,10 -(4,6-dihydroxybenzene-1, 3-diyl)bis(3-aryl/heteroarylpropane-1,3-dione) 3a–3f. The compounds were fully characterized using spectroscopic analyses and tested for their antibacterial 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.