Synthesis and cytotoxic activity of N-substituted thiosemicarbazones of 3-(3,4-methylenedioxy) phenylpropanal

Article abstract of DOI:10.1016/S0014-827X(97)00022-0

Five new N-substituted thiosemicarbazones of 3-(3,4-methylenedioxy) phenylpropanal were synthesized. Safrole, a natural product obtained from sassafras oil (Ocotea pretiosa), was oxidized to alcohol using BH₃-THF and H₂O₂, followed by oxidation to aldehyde using pyridinium dichromate (PDC) and condensation with five N-substituted derivatives of thiosemicarbazide. Tests were performed to evaluate the cytotoxic activity with continuous chain KB cells (epidermoide carcinoma of the floor of the mouth). Compounds 5 and 6 showed IC₅₀ values of 1.5 and 4.6 μg/ml, respectively.