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

Abstract

Abstract1,3‐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, 1H‐NMR, 13C‐NMR and mass spectra). The investigated compounds were screened for their cytotoxicity, i.e. compounds 19, 20 and 22 exhibited highly potential antitumor activity.