Design, Synthesis of Novel Thiourea and Pyrimidine Derivatives as Potential Antitumor Agents

1,3-Bis-(arylidene)thiourea derivatives (11a-c) were prepared by reacting thiourea (9) with bezaldehyde, p-chlorobenzaldehyde or p-anisaldehyde (10a-c) respectively. Further reaction of (11b) with acetyl acetone, ethyl acetoacetate, malononitrile and acetic anhydride gave tetrahydropyrimidine-2-thiones (12-14) and 1,3-diacetyl thiourea (15). Compound (11b) reacted with chloroacetyl chloride to give the corresponding pyrimidin-4-one derivative (16). Reaction of (12-14) with acetic acid in aqueous sodium nitrite yielded the corresponding oxime derivatives (17-19). The triazole (20) was achieved via refluxing of (19) in dimethylformamide. Reaction of (16) with mercaptoacetyl chloride gave the sulfanyl-acetic acid (21) which afforded the dihydrazinyl (22) up on treatment with hydrazine hydrate. Newly synthesized compounds ware characterized by elemental analyses and spectral data (IR, H-1-NMR, C-13-NMR and mass spectra). The investigated compounds were screened for their cytotoxicity, i.e. compounds 19, 20 and 22 exhibited highly potential antitumor activity.