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Synthesis and anticancer evaluation of some fused coumarino-[4,3-d]-pyrimidine derivatives

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Abstract

7- or 9-substituted-2-amino-4-hydroxy-7-methoxy-5H-chromeno-[4,3-d]-pyrimidine-5-one, 3a,b, were prepared via cyclocondensation of 6- or 8-substituted-3-ethoxycarbonyl coumarin, 2, with guanidine hydrochloride in presence of anhydrous potassium carbonate. Acetylation and alkylation of compounds with acetic anhydride and ω-bromomethyl aryl ketones yielded the corresponding N-acetyl derivatives, 4a,b, and 8- or 10-substituted-5-hydroxy-1-p-tolyl-6-H-chromeno[3,4-e] imidazo[1,2-a] pyrimidine-6-one, 5a,b,. Treatment of compound 3a with ethylchloroacetate and methyl acrylate afforded the corresponding benzopyrano-[4,3-d]-imidazolidino-[2,1-b]-pyrimidine, 6, and benzopyrano-[4,3-d]-pyrimidino-[2,1-b]-pyrimidine, 7, respectively. Some of the new compounds were evaluated for cytotoxicity activity against a hepatocellular carcinoma cell line.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt

    M. H. Sherif

  2. Chemistry Department, Faculty of Science, Port-Said University, Port-Said, Egypt

    Amal M. Yossef

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  1. M. H. Sherif
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  2. Amal M. Yossef
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Correspondence to M. H. Sherif.

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Sherif, M.H., Yossef, A.M. Synthesis and anticancer evaluation of some fused coumarino-[4,3-d]-pyrimidine derivatives. Res Chem Intermed 41, 383–390 (2015). https://doi.org/10.1007/s11164-013-1199-8

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  • DOI: https://doi.org/10.1007/s11164-013-1199-8

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