Synthesis of some quinazolinone derivatives using magnetic nanoparticles-supported tungstic acid as antimicrobial agents
- 13 Downloads
Quinazolinones are appealing materials because of their precious biological effects. In this study 10 new quinazolinone derivatives (4a–4j) were synthesized via an efficient three-component condensation reaction between anthranilic acid, acetic anhydride and different amines. This process was carried out for the first time in the presence of catalytic amount of magnetic nanoparticle supported tungstic acid, under solvent-free condition. The acidic catalyst can be easily reusing by an outward magnetic field after completion the reaction without any uncleanness. Chemical structures of the products were confirmed by spectroscopic methods such as: 1HNMR and 13CNMR, IR and elemental analysis. Antifungal and antibacterial activities were evaluated against different species of microorganisms including gram positive and gram negative bacteria as well as fungi. Broth microdilution method as recommended by clinical and laboratory standard institute was used for this purpose. The results show compounds 4h had the best antibacterial and antifungal activity against the examined bacteria and fungi. Compounds 4a–d and 4f also showed good activity against some species.
KeywordsQuinazolinone Synthesis Antimicrobial Antifungal
Financial assistance from the Shiraz University of Medical Sciences by way of grant number 94-01-36-9621 is gratefully acknowledged.
- 7.P.V. Acharyulu, P. Dubey, P. Prasada Reddy, T. Suresh, Synthesis of new 4 (3H)-quinazolinone derivatives under solvent-free conditions using PEG-400. ARKIVOC 11(3), 104–111 (2008)Google Scholar
- 9.A. Amin, D. Mehta, S. Samarth, Biological Activity in the Quinazolone Series. Progress in Drug Research/Fortschritte der Arzneimittelforschung/Progrès des recherches pharmaceutiques (Springer, Berlin, 1970), pp. 218–268Google Scholar
- 16.E. Jafari, M.R. Khajouei, F. Hassanzadeh, G.H. Hakimelahi, G.A. Khodarahmi, Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities. Res. Pharm. Sci. 11(1), 1 (2016)Google Scholar
- 17.T.P. Selvam, P.V. Kumar, Quinazoline marketed drugs. Res. Pharm. 1(1), 1–21 (2015)Google Scholar
- 20.G. Khodarahmi, E. Jafari, G. Hakimelahi, D. Abedi, M.R. Khajouei, F. Hassanzadeh, Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities. Iran. J. Pharm. Res. IJPR 11(3), 789 (2012)Google Scholar
- 25.H. Sharghi, M. Jokar, Al2O3/MeSO3H: a novel and recyclable catalyst for one-pot synthesis of 3, 4-dihydropyrimidinones or their sulfur derivatives in Biginelli condensation. Synth. Commun.®. 2009;39(6):958–979Google Scholar
- 33.National Committee for Clinical Laboratory S, Reference Methods for Broth Dilution Antifungal Susceptibility Testing of Yeast: Approved Standar (National Committee for Clinical Laboratory Standards, Wayne, 2002)Google Scholar
- 34.Standards NCfCL, Reference Methods for Broth Dilution Antifungal Susceptibility Testing of Yeast: Approved Standar (National Committee for Clinical Laboratory Standards, Wayne, 2002)Google Scholar
- 35.M.J. Ferraro, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically (NCCLS, Wayne, 2000)Google Scholar
- 39.M. Farahi, B. Karami, S. Alipour, L.T. Moghadam, Silica tungstic acid as an efficient and reusable catalyst for the one-pot synthesis of 2-amino-4H-chromene derivatives. Acta Chim. Slov. 61, 94–99 (2014)Google Scholar