The corresponding hydrazones and thiosemicarbazones were synthesized via the reaction of pinostrobin hydrazone with carbonyl compounds (aromatic aldehydes, acetone) or alkyl(aryl)isothiocyanates, respectively. The new pinostrobin derivatives showed significant cytotoxicity (MTT-assay) against human tumor cell models.Keywords: pinostrobin hydrazone, (4E)-benzylidenehydrazones, thiosemicarbazones, cytotoxic activity.Flavonoids comprise flavones, flavanones, flavonols, and isoflavones and constitute a large and important group of plant polyphenolic compounds. Available flavanones include pinostrobin (1), which was isolated from Populus balsamifera L.[1]. Pinostrobin exhibits antiproliferative [2], antimicrobial [3], neuroprotective [4], and anti-inflammatory [5] properties. The ointment Topolin and tincture Efmatol were formulated from extracts of P. balsamifera buds as antiperiodontitis and antiinflammatory agents, the active ingredient of which was the flavonoid 1 [6,7]. Considering the availability of 1, the preparation of new derivatives with high specific biological activity is critical.The preparation of pinostrobin oxime, for which hepatoprotective activity was found [8], has been reported. Halosubstituted pinostrobin derivatives were synthesized [9]. Also, prenylation of 1 was described and the cytotoxicity of new derivatives against human tumor cells was studied [10].The goals of our work were to develop a method for producing pinostrobin hydrazone; to study its reactions with aromatic aldehydes, phenylisothiocyanate, alkylisothiocyanates, and acetone; and also to study the cytotoxic activity of several derivatives against human tumor cell models.Treatment of 1 with an excess of hydrazine hydrate was reported [8] to give pinostrobin hydrazone (2). Our experiments showed that 2 was readily formed via the reaction of 1 with hydrazine hydrate in EtOH. Pyrazole 2a that could be produced by cleavage of the pyrone ring was not observed (Scheme 1).