Synthesis and antifungal activity screening of some novel 7–substituted –2–hydroxy–quinoline schiff bases

Authors

  • M. R. Pradeep Kumar Department of Pharmaceutical Chemistry, KLEU’s College of Pharmacy, Hubli – 580031, Karnataka

Keywords:

Quinoline, antifungal, two fold dilution, fluconazole, Schiff base

Abstract

With an objective of synthesizing some novel, potent and broad spectrum antifungal activity having compounds, here some novel quinoline derivatives are reported. Initially 7-substituted-2-cholro-3-formylquinolines were prepared using well known Vilsemeir-Hack reagent method. These on microwave irradiation with 4M HCl yielded 7-substituted-2-hydroxy quinoline-3-carbaldehydes I(a, b), which on further treatment with different substituted hydrazides yielded the novel Schiff bases of quinoline II(a-f). The structure of all newly synthesized compounds was confirmed by spectral study such as IR, 1H NMR, 13C NMR and mass spectroscopy. All the synthesized compounds were screened for in-vitro antifungal activity by two fold serial dilution method using fluconazole as the standard drug. Compounds II a, II b and II d showed significant antioxidant activity

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References

Chen Y, Chen I.L, Lu C.M, Tzeng C.C, Tsao L.T, Wang J.P. Synthesis and anti-inflammatory evaluation of 4-anilinofuro[2,3-b] quinoline and 4-phenoxyfuro [2,3-b] quinoline derivatives. Bioorg Med Chem.,2004;12: 387-392.

Bawa S, Kumar S. Synthesis of schiff’s bases of 8-methyl tetrazolo [ 5-a] quinoline as potential anti inflammatory and antimicrobial agents. Ind J Chem., 48B 2009;1:142-5.

de Souza M.V, Pais K.C, Kaiser C.R, Peralta M.A, Ferreira M.L, Lourenco M.C. Synthesis and in-vitro antitubercular activity of a series of quinoline derivatives. Bioorg & Med Chem.,2009;17: 1474-1480.

Pradeep Kumar M.R, Joshi S.D, Dixit S.R, Kulkarni V.H. Synthesis, antibacterial and antitubercular activities of some novel quinoline derivatives. Ind J Heterocycl Chem., 2014; 23: 353-358.

Lilienkampf A, Mao J, Wan B, Wang Y, Franzblau S.G, Kozikowski A.P. Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis. J Med Chem., 2009; 52:2109-2118.

Jamal M.A, Mohammed K, Manogaran P.S, Adnan A.B, El-Sayed O.A, Al-Hussein K,. Hassan Y.A, Al-Khodairy F.M. Evaluation of cytotoxic potential of newly synthesized antiviral aminopyrazoloquinoline derivatives. Int J Biomed Sci., 2007; 3: 194-198.

Pretorius S.I, Breytenbach W.J, de Kock C, Smith P.J, N'Da D.D. Synthesis, characterization and antimalarial activity of quinoline-pyrimidine hybrids. Bioorg & Med Chem., 2013; 21: 269-277.

Kaur K, Jain M, Reddy R.P, Jain R. Quinolines and structurally related heterocycles as antimalarials. Eur J Med Chem., 2010; 45: 3245-3264.

Vaidya A, Jain A.K, Kumar P, Kashaw S.K, Agrawal R.K . Predicting anti-cancer activity of quinoline derivatives; CoMFA and CoMSIA approach. J Enzyme Inhib Med Chem., 2011; 26: 854-861.

Chen Y, Hung H, Lu C, Li K and Tzeng C. Synthesis and anticancer evaluation of certain indolo[2,3-b] quinoline derivatives Bioorg & Med Chem., 2004;12:6539-6546.

Joshi S.D, Joshi A, Vagdevi H.M, Vaidya V.P, Gadaginamath G.S. Synthesis of some quinolinylpyeazoles as potential antibacterial and antitubercular agents. Ind J Heterocycl Chem., 2010; 19: 221-225.

Shirwaiker A, Rajendran K, Dinesh Kumar C. In vitro antioxidant studies of Annona squamosa Linn. Leaves. Ind. J. Expl. Biol., 2004; 42: 803-807.

Maguire M.P, Sheets K.R, McVety K, Spada A.P, Zilberstein A. A new series of PDGF receptor tyrosine kinase inhibitors: 3-substituted quinoline derivatives. J Med Chem 1994; 37: 2129-2137.

Ramaiah M. Anbala N.N, GunasekaranV and Leonard J.T. Synthesis Anticonvulsant and Antihypertensive Activities of 8Substituted Quinoline Derivatives. Bio.l Pharm. Bull 2004; 27:1683-1687.

Jarrahpour A, Khalili D, De Clercq E, Salmi C, Brunel J.M. Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of isatin and Their Derivatives. Molecules 2007; 12: 1720-1730.

Published

2016-12-09

How to Cite

Kumar, M. R. P. (2016). Synthesis and antifungal activity screening of some novel 7–substituted –2–hydroxy–quinoline schiff bases . Journal of Applied Pharmaceutical Research, 4(4), 05-09. Retrieved from https://japtronline.com/index.php/joapr/article/view/65

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Articles