A series of novel 7-Hydroxy-3-methyl-2-phenyl-8(imino) chromone compounds 4(a-p) were prepared by reacting 8- formyl-7-hydroxy-3-methyl-2-phenyl- chromones with selected amines. The amines were so selected, which facilitate the comprehend survey of the Structure-Activity Relationships. This was accompanied with the reckoning of Lipophilicity (log P), Molar refractive index and molecular weight of the synthesized compounds. All these new compounds were characterized by 1H-NMR, 13C-NMR and Mass spectrometry. The synthesized compounds were screened for in-vitro antimicrobial activities. The Antagonist effects of the different substituent of novel compounds on the antimicrobial activity were discussed. Lead like /drug like qualities of the new compounds was devised by quantitative characterization of the compounds with their computed physicochemical properties.