In the present study, three series of dimethylamino curcuminoids viz. 4-phenylaminomethyl curcumin (3a–d), arylidene curcumin (3e) and pyrazole curcumin (3f–i) derivatives have been synthesized and studied for their in vitro anti-inflammatory, antioxidant and antibacterial activities. Synthesized dimethylamino curcuminoid derivatives namely 3d, 3e, 3h and 3i have shown potent anti-inflammatory properties than parent curcumin. Molecular docking interactions of dimethylamino curcuminoids derivatives against cyclooxygenase enzymes (COX-1 and COX-2) were studied.