A series of 11 oxadiazole analogues were subjected to molecular properties prediction and drug likeness by Molinspiration and MolSoft software, lipophilicity and solubility parameters using ALOGPS 2.1 program. The compounds followed the Lipinski "Rule of five" were synthesized for antimicrobial screening as oral bioavailable drugs/leads. Further the structure of the synthesized compounds was confirmed by spectral analyses (IR, NMR and mass) and the compounds (4a-k) were evaluated for antibacterial and antifungal activities as per the standard protocol. N-(2-Methylphenyl)-5-(4-chlorophenyl)-1, 3, 4-oxadiazol-2-amine, 4c was found to have maximum antibacterial activity while N-(2-methylphenyl)-5-(4-hydroxyphenyl)-1, 3, 4-oxadiazol-2-amine, 4d showed maximum antifungal activity.