Document Type : Original Article
Authors
1
Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, Egypt.
2
Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt.
3
Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo 11757, Egypt.
4
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig 44519, Egypt.
Abstract
A new series of 5-8 and 10 & 11 was prepared based on 4-(4-chlorophenyl)-2-mercapto-6- oxo-1,6- dihydropyrimidine-5-carbonitrile 4 and 4-(4-chlorophenyl)-2-hydrazinyl-6-oxo-1,6- dihydropyrimidine-5-carbonitrile 9 as key materials. 7-(4-chlorophenyl)-2-(4-methoxybenzylidene)-3,5-dioxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carbonitrile 5 was produced by condensing compound 4 with 4-methylbenzaldehyde and monochloroacetic acid. Whereas 4-(4-chlorophenyl)-2-mercapto-6-oxo-1-tosyl-1,6-dihydropyrimidine-5-carbonitrile 6 was obtained through the combination compound 4 with toluene sulfonyl chloride under reflux. The compound 4 went through Mannish reaction and esterification reaction with ethyl chloroacetate, to yield the dimer of 2,2'-(((1,4-phenylenebis(azanediyl))bis(methylene))bis(sulfanediyl))bis-(4-(4-chlorophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile 7 and 2-((4-(4-chlorophenyl)-5-cyano-6-oxo-1,6-dihydro-pyrimidin-2-yl)thio)acetate 8, respectively. Furthermore, Schiff base like 4-(4-chlorophenyl)-6-oxo-2-(2-(1-phenylethyl-idene)hydrazinyl)-1,6-dihydropyrimidine-5-carbonitrile 10 was constructed by condensing compound 9 with acetophenone. The synthesis of the triazole like 7-(4-chlorophenyl)-5-oxo-3-thioxo-1,2,3,5-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carbonitrile 11 was obtained from the reaction of compound 9 with carbon disulfide in a water bath. The newly manufactured compounds were defined using spectral data (FT-IR), mass spectroscopy, 1HNMR, 13CNMR and elemental analysis. The prepared compounds are applied to microorganisms (Staphylococcus aureus and Escherichia coli) as well as fungi (Candida albicans and Aspergillus niger). Also, the prepared compounds were assessed their cytotoxic behavior on tumor cells (MCF-7) and were given high inequality in the activities and inhibiting rates of proliferation against the cancer cell lines under investigation.
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