Synthesis and In Vitro Antibacterial Evaluation of Some Novel Annulated Quinazolinone Derivatives
- Autores: El-Shenawy A.1
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Afiliações:
- Chemistry Department, Faculty of Science
- Edição: Volume 88, Nº 8 (2018)
- Páginas: 1712-1719
- Seção: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222378
- DOI: https://doi.org/10.1134/S107036321808025X
- ID: 222378
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Resumo
A series of novel substituted quinazoline derivatives are synthesized. Antibacterial tests demonstrate their high activity against Gram-positive and Gram-negative bacteria. 3-[4-(2-Bromoacetyl)-phenyl]-2-phenylquinazolin-4(3H)-one 2 and 3-oxo-3-{[4-(4-oxo-2-phenylquinazolin-3(4H)-yl]phenyl}propanenitrile 3 are used as intermediates in the synthesis of functionalized heterocyclic derivatives such as 3-[4-(2-amino-thiazol-5-yl)phenyl]-2-phenylquinazolin-4(3H)-one 4, Schiff base 5, 3-{5-(4-[4-oxo-2-phenylquinazolin-3(4H)-yl]phenyl)thiazol-2-yl}-2-phenylthiazolidin-4-one 6, and N-phenyl acetohydrazonoyl derivatives 7a, 7b. The latter react with ethyl cyanoacetate with formation of 9a, 9b. Chalcone 10 is the key intermediate in the synthesis of N-acetylpyrazole derivative 11 and 1-thiocaramoyl pyrazole derivative 12. Treatment of 12 with chloroacetyl chloride and compound 2 leads to formation of compounds 13 and 14, respectively. Treatment of compound 3 with phenyl isothiocyanate affords the corresponding quinazolin-3(4H)-yl acrylonitrile derivative 15, which reacts with phenyl hydrazine to give the corresponding product 16. The synthesized compounds are characterized by IR, MS and 1H NMR spectra.
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Sobre autores
A. El-Shenawy
Chemistry Department, Faculty of Science
Autor responsável pela correspondência
Email: aielshenawy@gmail.com
Egito, Benha, 13518
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