One-pot Synthesis of 1,2,3,4-Tetrahydropyrimidin-2(1H)-thione Derivatives and their Biological Activity

Salem, Marwa 


Abstract


© 2015 HeteroCorporation. 2-Thioxo/oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives 2a, 2b, 2c, 2d were prepared by the reaction of ethyl acetoacetate and thiourea or urea with aldehydes using NH4Cl as a catalyst. Compounds 2a and 2c reacted with mono and bihalogenated compounds such as ethyl iodide, chloroacetonitrile, epichlorohydrin, acetyl chloride, ethyl bromoacetate, chloroacetic acid, chloroacetylchloride, and/or oxalyl chloride to afford compounds 3, 4a, 4b, 5, 6a, 6b, 7, 8, 9 and 10, respectively. Compounds 2a, 2c, and 7 were allowed to react with p-fluorobenzaldehyde to yield the corresponding products 11a, 11b, and 12, respectively. Oxidation of 2a and 2c gave 2b, 13a, 13b, 14, 15, 16 dependent on the oxidizing agent used. Vilsmeiere-Haack formylation of 2a and 2b with POCl3/DMF afforded 17a and 17b. Chlorination of 2b and 2d gave the chlorinated derivative 18a and 18b, which reacted with thiourea to give thioureidopyrimidine 19a and 19b. Reactions of 2a with hydrazine monohydrate, semicarbazide hydrochloride, and sodium hydroxide gave compounds 20, 21, 22, respectively. The cytotoxicity and in vitro anticancer evaluation of some prepared compounds have been assessed against two different human tumor cell lines including breast adenocarcinoma MCF-7 and human hepatocellular carcinoma HepG2. Antimicrobial and antioxidant activities of some compounds were investigated. The newly synthesized compounds were characterized by IR,1H-NMR,13C-NMR, and mass spectral data.


Other data

Issue Date 1-Mar-2016
Journal Journal of Heterocyclic Chemistry 
URI http://research.asu.edu.eg/handle/123456789/167674
DOI 2
https://api.elsevier.com/content/abstract/scopus_id/84928728866
545
53
10.1002/jhet.2358


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