In the present study, a new series of 3,6-disubstituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles (4aj) have been synthesized by condensing 3-substituted-4-amino-5-mercapto-1,2,4-triazoles (1a–b) with various 3-substituted-pyrazole-4-carboxylic acids (3a–e) in the presence of POCl3. The structures of newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR, and mass spectroscopic studies. Structure of the compound 4b was also confirmed by recording the single crystal X-ray structure. All the synthesized compounds were screened for their anti-inflammatory activities by carrageenan induced paw edema method. Anti-inflammatory screening indicated that, compounds 4d, 4e, and 4h were found to be biologically active whereas remaining compounds showed poor anti-inflammatory activity. Also molecular docking studies were also performed for compounds which showed good anti-inflammatory activity.