In this study, two new thieno[2,3-b]pyridine derivatives (2 and 3) have been synthesized and characterized by single X-ray diffraction. While compound 2 crystallizes in monoclinic space group P2₁/c, compound 3 crystallizes in triclinic space group P. These compounds were further subjected to molecular docking simulation with p38 alpha MAP kinase to understand the binding interaction mechanism, in addition to that ADMET analysis was also performed to explore the title compounds to characterize the future drug candidate. To rationalize their structure-activity relationship, a DFT study based on the B3LYP/6-311++G** theoretical level was also done in this study.