A series of cinnamic acid derivatives, amides (1-12) and esters (13-22), were synthesized, and structureactivity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1-10, 12-18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxyindole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9-11, 15, 17-22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer's disease.Key words cinnamic acid amide; cinnamic acid ester; monoamine oxidase; cholinesterase; antioxidant; Alzheimer's disease Plant secondary metabolites are important sources of bioactive constituents that promote health. Natural products have long played a significant role in the development of new therapeutic leads. For example, phenolic compounds have been shown to prevent oxidative stress, a condition known to cause cell injury and death and to exacerbate the development of several age-related chronic pathologies like cancer, and neurodegenerative diseases such as Alzheimer's and Parkinson's diseases.