Design-Syntheses, Characterization and Biological Activity Studies of Azobenzen-P,Pꞌ-Di(3,1-Benzoxazin-4-One-2yl) and Azobenzen-P,Pꞌ-Di[(3- Substituted 3(4H)Quinazolinone-2yl] Derivatives

Abstract

Sixteen azobenzene-p,pežŒ-di[3-substituted-4(3H)quinazolinone-2yl] were synthesized from reaction of azobenzenp, pežŒ-di(3,1-benzoaxzin-4-one-2yl) with amino-moieties nucleophlies, like hydrazinehydrate, hydroxylamine, p,toluidine, p-aminobenzene sulphonamide, 2-pyrimidine, 5-nitro-2-aminopyridine, ethyleneamine,5-(p-bromo) phenyl-2-aminothiazol, p,pežŒ-diamino diphenyl sulphone, quinidine hydrochloride, urea, thiourea, 3,5-dimethyl- 2-phenyl-4-aminopyrazolin-3-one, N(5-methyl-3-isoxazolyl)-p-aminobenzen sulphonamide, semicarbazide and thiosemicarbazide, in a molar ratio (1:2) respectively. azobenzen-p,pežŒ-di(3,1-benzoaxzin-4-one-2yl), was synthesized by following serial synthetic pathway. Reductive-condensation of p-nitrobenzoic acid in basic media give azobenzenp, pežŒ-dicarboxylic acid, then treated with thionyl chloride to give azobenzen-p,pežŒ-diacid chloride. It condensed with anthranilic acid to give azobenzen-p,pežŒ-[(dibenzoic acid-2yl)dicarboxamide], upon treatment with thionyl chloride give azobenzen-p,pežŒ-di(3,1-benzoaxzin-4-one-2yl). All synthesized compounds characterized by FTIR, 1HNMR, 13CNMR and mass spectral analyses. All synthesized azobenzen-p,pežŒ-di(3,1-benzoaxzin-4-one-2yl), and sixteen azobenzenep, pežŒ-di[3-substituted-4(3H)quinazolinone-2yl] compounds, were examined as antibacterial agents against gm(+ve and –ve) bacteria, and antifungal agents. Results showed abroad extended to moderate effects as antibacterial and antifungal agents.