Suitably substituted cinnnamamides were successfully synthesized in 11-92% yield. Majority of the cinnnamamides displayed IC50 greater than acarbose. Their α-glucosidase inhibitory activity greatly depended on their structure with electron-withdrawing groups on the cinnamoyl aromatic ring causing increased inhibition activity. The synthesized cinnnamamides showed acceptable physicochemical and pharmacokinetics characteristics with little toxicity indicating their potential use as lead drug candidates. Molecular docking studies of these compounds were also conducted to elucidate their mechanism of action. Overall, these cinnnamamides show potential as lead structures for further optimization as α-glucosidase inhibitors.