Volume 57, Issue 1 pp. 69-80
ARTICLE

Synthesis and anticancer evaluation of some novel N,O,S heterocyclic compounds pendant to 3-methyl-5-cyano-6-(3,4-dimethoxyphenyl)pyrimidine and other related fused pyrimidines

Rasha S. Gouhar

Corresponding Author

Rasha S. Gouhar

Therapeutical Chemistry Department, National Research Centre, Giza, Egypt

Correspondence

Rasha S. Gouhar, Therapeutical Chemistry Department, National Research Centre, Giza 12613, Egypt.

Email: [email protected]

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Mohsen M. Kamel

Mohsen M. Kamel

Therapeutical Chemistry Department, National Research Centre, Giza, Egypt

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Ahmed A.F. Soliman

Ahmed A.F. Soliman

Drug Bioassay-Cell Culture Laboratory, Department of Pharmacognosy, National Research Centre, Giza, Egypt

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First published: 11 December 2019
Citations: 1

Abstract

The key starting compound 5-cyano-6-(3,4-dimethoxyphenyl)-2-thiouracil (1) was synthesized and allowed to undergo electrophilic substitution with methyl iodide to give the corresponding 6-(3,4-dimethoxyphenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (2). Nucleophilic substitution on compound 2 with hydrazine hydrate led to the corresponding 2-hyrazinopyrimidone intermediate 3. Compound 3 underwent several substitution and cyclization reactions with β-ketoester, β-ketone, alkyl halides, arylisothiocyanate, or aromatic aldehydes followed by cyclization reactions to give the corresponding N,O,S heterocyclic compounds incorporated into pyrimidine moiety and/or the related S-triazino[3,4-b]pyrimidine derivatives 4-18. Anticancer evaluation of some representative examples of newly synthesized compounds was carried out against MCF-7, HCT116 cell lines. Some of the newly synthesized compounds showed significant activity.

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