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A new series of N'-substituted benzylidene-2-(4-oxo-2-phenyl-1,4-dihydroquinazolin-3(2H)-yl)acetohydrazide ( 5a-5h ) has been synthesized, characterized by FT-IR, NMR spectroscopy and mass spectrometry and tested against human monoamine oxidase (MAO) A and B. Only (4-hydroxy-3-methoxybenzylidene) substituted compounds gave submicromolar inhibition of MAO-A and MAO-B. Changing the phenyl substituent to methyl on the unsaturated quinazoline ring ( 12a-12d ) decreased inhibition, but a less flexible linker ( 14a-14d ) resulted in selective micromolar inhibition of hMAO-B providing insight for ongoing design., Competing Interests: There are no conflicts to declare., (© 2020 The Authors.)