Pyrazole derivatives IIa–l have been synthesized by condensation of chalcones Ia–f with hydrazine hydrate and phenyl hydrazine under microwave irradiation in good yields. Oxadiazole derivatives IVa–f have been synthesized by condensation of N0 -hydroxypicolinamidine, N0 -hydroxy isonicotinamidine, N0 -hydroxypyrazine-2-carboxamidine with 2,5 dimethoxybenzaldehyde and 3-methoxy-4-hydroxy benzaldehyde, respectively. Structures assigned to IIa–l and IVa–f are fully supported by correct spectral and analytical data. All compounds (IIa–l & IVa–f) have been screened for anti-inflammatory and anticancer activities. Compounds IIj, IIk, and IVb exhibited good anti-inflammatory activity, while, IIa, c, j, and IVd showed better anticancer activity against four and three cancer cell lines, respectively.