Objective of this research was to do synthesis and anti-inflammatory and antiproliferative evaluation of new synthetic analogues. Method: Synthesis of novel pyrazole derivatives from chalcone intermediates carried out using microwave. Compounds were characterized using IR, NMR, LCMS spectra. Compounds with dimethyl-amino, chloro ring substitution shown good yield whereas those with pyridine ring substitution and involving diphenyl ring shown optimum yield. Microwave assisted synthesis is preferred as green method for final step of reaction. Derivatives screened for in vitro anti-inflammatory potential. As from some literature it is clear that compounds having anti- swelling property further may result in effective anticancer agent so we have checked series for anticancer potential against MCF-7 cell line Result: Compound 1a,1f shown remarkable in vitro anti-inflammatory score. These compounds carry -OCH3, -OCF3, ring substitution respectively. As from literature review it was revealed that Cox inhibition is one of the mechanism for anti-inflammatory activity; hence to predict probable mechanism for anti-inflammatory activity docking interactions of synthesized compounds against COX I enzyme was studied. For comparative analysis anti-inflammatory drug Ibuprofen used as a standard. Compound 1a, 1f ,1g exhibited a good degree of binding interactions in the selected binding site region with binding score of -7.8, -8.8. -8.0, kcal/mol which is equal to and better than Ibuprofen (-7.8 kcal/mol). 1f shows moderate cytotoxic activity against MCF7 cell line. Conclusion: Compound 1f shown promising anti-inflammatory potential than Ibuprofen. Further moderate anticancer activity is obtained for it (GI50- 78.4µg/ml) against MCF-7 cell line. Binding interactions were checked by docking against EGFR.