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Journal of the Brazilian Chemical Society

versão impressa ISSN 0103-5053versão On-line ISSN 1678-4790

Resumo

SAHU, S. K. et al. Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4(3H)-ones Schiff bases. J. Braz. Chem. Soc. [online]. 2008, vol.19, n.5, pp.963-970. ISSN 0103-5053.  http://dx.doi.org/10.1590/S0103-50532008000500023.

The 3-amino-2-methylquinazoline/6-bromo-2-methylquinazoline-4(3H)-ones, 2a,b, on treatment with 2,3-indolinedione in the presence of traces of glacial acetic acid yielded 3-{(2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methylquinazolin/6-bromo-2-methylquinazolin-4-(3H)-ones, 3a,b, which on condensation with various secondary amines and formaldehyde in ethanol afforded title compounds 3-{(1'-alkyl/arylaminomethyl-2'-oxo-1',2'-dihydroindole-3'-ylidene)amino} -2-methyl-6-quinazolin-4-(3H)-ones, 4a1-6 and 4b1-6. C, H, N analysis, infrared spectroscopy, 1H NMR, and mass spectroscopy allowed the identification of the synthesized compounds, which were investigated for their antimicrobial, analgesic, anti-inflammatory and antihelmintic activities. The results of the biological activities revealed that the compounds 4a3, 4a4 and 4b6 exhibited significant analgesic and anti-inflammatory activities. Compounds 4b5 and 4b6 showed antihelmintic activity when tested against Pheretima posthuma.

Palavras-chave : 2-methylquinazolin-4(3H)-one; bromoderivative; 2,3-indolinedione; Mannich base; antimicrobial.

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