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

被引:21
作者
Abu-Hashem, Ameen A. [1 ,2 ]
Badria, Farid A. [3 ]
机构
[1] Natl Res Ctr, Photochem Dept, Heterocycl Unit, Giza, Egypt
[2] Jazan Univ, Dept Chem, Fac Sci, Jazan 2097, Saudi Arabia
[3] Mansoura Univ, Dept Pharmacognosy, Fac Pharm, Mansoura 35516, Egypt
关键词
Thiourea; Pyrimidine; Oxime; Triazole; Cyclization; Hydrazinyl; Antitumor activity; ANTIOXIDANT; ASSAY;
D O I
10.1002/jccs.201400351
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:506 / 512
页数:7
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