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On the basis of the knowledge from traditional herbal and folk medicine, flavonoids are among the most studied chemical classes of natural compounds for their potential activity as phosphodiesterase 5 (PDE5) inhibitors. We here describe the preparation of a semi-synthetic hydrazone derivative of quercetin, 2-(3,4-dihydroxyphenyl)-4-(2-(4-nitrophenyl)hydrazono)-4H-chromene-3,5,7-triol, that was obtained via a single-step modification of the natural compound. The product was characterized by NMR, mass spectrometry and HPLC. Preliminary molecular modeling studies suggest that this compound could efficiently interact with PDE5.