The free –COOH of NSAIDs is thought to be one of the causes that responsible for the GI irritation associated ,in this study NSAIDs were conjugated with gabapentin through ester bond using chloroacetyl chloride as a spacer. The methodology of this work consist three steps: Gabapentin was reacted with para substituted benzaldehyde to protect the free amine group via converting it to  imine (Schiff base) II(1a-b) , Esterification by the reaction of  NSAID with chloroacetyl chloride to give the  corresponding ester III , The reaction of III with II(1a-b) to give the final product III(1a-h). The structures of these compounds were confirmed and characterized by attenuated total reflectance -Fourier transform infrared spectroscopy (ATR-FTIR ) ,1HNMR and physicochemical properties . In silico evaluation methods were done before synthesis through molecular docking via genetic optimization for ligand docking (Schrödinger) Suite software with COX-1 enzyme, the prepared compounds showed good activity against standard compounds, theoretically and experimentally. An ADMET analysis was performed to anticipate the pharmacokinetic properties of the final synthesized drugs and indicate that the final compounds contain drug-like features.Also the preliminary pharmacological Evaluation . Synthesized compounds were screened for their antimicrobial activity, and show moderate to high inhibition against both gram-positive and gram-negative bacteria, and a high antifungal activity. The anti-inflammatory activity was also tested for the final compounds and it showed a good activity .