SYNTHESIS, ANTIMICROBIAL AND ANTI-INFLAMMATORY ACTIVITY OF NEWLY SYNTHESIZED ISOXAZOLINE INCORPORATED 2-QUINOLONES
Abstract
A series of novel substituted 1-amino-3-(5-phenyl-4,5-dihydroisoxazol-3-yl) quinolin-2(1H)-one (AJI1-AJI8) have been synthesized upon reaction with 1-amino-3-cinnamoyl-quinolin-2(1H)-one by using hydroxylamine hydrochloride as cyclising agent in alcohol medium. The intermediate chalcones 1-amino-3-cinnamoyl-quinolin-2(1H)-one (AJC1-AJC8) were synthesized by condensing 3-acetyl-1-amino-quinolin-2-one with different substituted benzaldehyde in presence of 40% ethanolic KOH. The title compounds obtained were characterized by IR, 1H NMR, mass spectra and elemental analysis. The synthesized compounds were screened for their antimicrobial and anti-inflammatory activity.
Keywords:
2-Quinolones, chalcones, isoxazoline, antimicrobial, anti-inflammatoryDOI
https://doi.org/10.25004/IJPSDR.2014.060208References
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2. Joseph B, Darro F, Behard A, Lesur B, Frydman A, Kiss R. 3-aryl-2-quinolone derivatives: Synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration. J Med Chem, 2002; 45: 2534-2555.
3. Ukrainets IV, Mospanova EV, Davidenko AA, Tkach AA, Gorokhova OV. 4-hydroxy-2-quinolones. Synthesis, structure and anti-inflammatory activity of 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl acetic acid and its derivatives. Chem Heterocycl Compd, 2012; 46(8): 974-986.
4. Uchida M, Tabusa F, Komatsu M, Morita S, Kanbe T, Nakagawa K. Studies on 2(1H)-quinolinone derivatives as gastric antiulcer active agents. Synthesis and antiulcer activities of optically active alpha-amino acid derivatives of 2(1H)-quinolinone and oxindole. Chem Pharm Bull (Tokyo), 1987; 35(2): 853-856.
5. AL-Omar MA, EL-Azab AS, EL-Obeid HA, Abdel H. Synthesis of some new 4(3H)-quinazolinone analogues. J Sandi Chem Soc, 2006; 10: 113.
6. Jin Y, Li HY, Lin LP, Tan JZ, Ding J, Luo XM. Synthesis and antitumor evaluation of novel-5-substituted-4-hydroxy-8-nitroquinazolines as EGFR signaling-targeted inhibitors. Bioorg Med Chem, 2005; 13: 5613.
7. Badadhe PV, Chavan NM, Mandhane PG, Joshi RS, Nagargoje DR, Gill CH. Synthesis and characterization of some novel isoxazolines and pyrazolines as potent antimicrobial agents. Indian J Chem (Sec B), 2011; 50B: 879-884.
8. Shah TK, Desai V. Synthesis and antibacterial studies of some novel isoxazoline derivatives. J Chil Chem Soc, 2007; 72(5): 443-449.
9. Kalirajan R, Rafick MHM, Sanker S, Jubie S. Docking studies, synthesis, characterization and evaluation of their antioxidant and cytotoxic activities of some novel isoxazole-substituted 9-anilinoacridine derivatives. Scientific World Journal, 2012; 1-6.
10. Shivkumar B, Nargund LVG. Synthesis, characterization and anti-inflammatory activity of some isoxazoline derivatives. Ind J Het Chem, 1998; 8: 27.
11. Al-Bayati RIH, Mahdi FR. Synthesis of novel 2-quinolone derivatives. Afr J Pure Appl Chem, 2010; 4(10): 228-232.
12. Toche RB, Kazi MA, Jachak MN, Desai AE. Synthesis and molluscicidal activities of quinolone substituted pyrazoline and isoxazoline derivatives. J Appl Sci Res, 2009; 6(6): 637-641.
13. Andrews JM. Determination of minimum inhibitory concentrations. J Antimicrob Chemother, 2001; 48(S1):5-16.
14. New OCED 425 guidelines. OCED guidelines for testing of animal. 2001; 1-26.
15. Winter CA, Risley EA, Nuss GW. Carrageenin-induced oedema in hind paws of the rats as an assay for anti-inflammatory drugs. Proc Soc Exp Bio Med. 1962; 111: 544-547.
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01-04-2014
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“SYNTHESIS, ANTIMICROBIAL AND ANTI-INFLAMMATORY ACTIVITY OF NEWLY SYNTHESIZED ISOXAZOLINE INCORPORATED 2-QUINOLONES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 2, Apr. 2014, pp. 124-7, https://doi.org/10.25004/IJPSDR.2014.060208.
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How to Cite
“SYNTHESIS, ANTIMICROBIAL AND ANTI-INFLAMMATORY ACTIVITY OF NEWLY SYNTHESIZED ISOXAZOLINE INCORPORATED 2-QUINOLONES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 2, Apr. 2014, pp. 124-7, https://doi.org/10.25004/IJPSDR.2014.060208.
