Citation: E.O. Moradi Rufchahi, H. Pouramir, M.R. Yazdanbakhsh, H. Yousefi, M. Bagheri, M. Rassa. Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone:Synthesis, UV-vis studies and biological activity[J]. Chinese Chemical Letters, ;2013, 24(05): 425-428.
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In this study, N,N'-di-(2-methylphenyl)malonamide was synthesized and reacted with polyphosphoric acid to afford 8-methyl-4-hydroxyl-2-quinolone. Eight novel azo disperse dyes were then synthesized by linking diazotized p-substituted aniline derivatives with 8-methyl-4-hydroxyl-2-quinolone. The solvatochromism of these azo dyes in various solvents was evaluated. All the compounds were then evaluated for their antibacterial activity against four bacteria, namely, Bacillus subtilis, Micrococcus luteus, Salmonella enterica, and Pseudomonas aeruginosa. The results showed that some of these compounds have high levels of antibacterial activity.
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-
[1]
[1] F. Takeshi, H. Terushi, F. Noriko, et al., Development of N-[11C]methylamino 4-hydroxy-2(1H)-quinolone derivatives as PET radio ligands for the glycine-binding site of NMDA receptors, Bioorg. Med. Chem. 17 (2009) 5665-5675.
-
[2]
[2] B. Refouvelet, C. Guyon, Y. Jacquot, et al., Synthesis of 4-hydroxycoumarin and 2,4-quinoinediol derivatives and evaluation of their effects on the viability of HepG2 cells and human hepatocytes culture, Eur. J. Med. Chem. 39 (2004) 931-937.
-
[3]
[3] A. Knierzinger, O.S. Wolfbeis, Syntheses of fluorescent dyes. IX. New 4-hydroxycoumarins, 4-hydroxy-2-quinolones, 2H,5H-Pyrano[3,2-c]benzopyran-2,5-diones and 2H,5H-Pyrano[3,2-c]quinoline-2,5-diones, J. Heterocyclic Chem. 17 (1980) 225-229.
-
[4]
[4] K. Holzach, G. Rosenberg, Azo Dyestuff, US Patent no. 1,969,463 (1934).
-
[5]
[5] K. Holzach, G. Rosenberg, Dyeing and Printing of Acetate Silk, US Patent no. 1,969,464 (1934).
-
[6]
[6] Th. Kappe, The‘pyrano route’to 4-hydroxy-2-quinolones and 4-hydroxy-2-pyridones, Ⅱ Farmaco 54 (1999) 309-315.
-
[7]
[7] H. Zollinger, Color Chemistry: Syntheses, Properties and Application of Organic Dyes and Pigments, 2nd ed., VCH, Weinheim, 1991.
-
[8]
[8] J.B. Dickey, N.Y. Rochester, Monoazo compounds containing a 4-hydroxyquinolone-2-group, US Patent no. 2,529,924 (1950).
-
[9]
[9] U. Buhler, Hydroxy quinolone monoazo dyestuffs, their preparation and use, US Patent no. 5,760,197 (1998).
-
[10]
[10] I. Sener, F. Karcı, N. Ertan, E. Kılıc, Synthesis and investigations of the absorption spectra of hetarylazo disperse dyes derived from 2,4-quinolinediol, Dyes Pigment 70 (2006) 143-148.
-
[11]
[11] E.O. Moradi-e-Rufchahi, Synthesis of 6-chloro and 6-fluoro-4-hydroxyl-2-quinolone and their azo disperse dyes, Chin. Chem. Lett. 21 (2010) 542-546.
-
[12]
[12] E.O. Moradi-e-Rufchahi, A. Ghanadzadeh, A study of solvatochromism in diazonium coupling products of 6-flouro-4-hydroxyl-2-quinolone, J. Mol. Liq. 160 (2011) 160-165.
-
[13]
[13] E. Ziegler, R. Wolf, R. Kappe, Eine einfache synthese des 4-hydroxycarboxytyrils und seiner derivate, Monatsch. Chem. 96 (1965) 418-422.
-
[14]
[14] E.O. Moradi Rufchahi, A. Ghanadzadeh Gilani, Synthesis, characterization and spectroscopic properties of some new azodisperse dyes derived from 4-hydroxybenzo[h]quinolin-2-(1H)-one as a new synthesized enol type coupling component, Dyes Pigment 95 (2012) 632-638.
-
[15]
[15] G.J. Lestina, T.H. Regan, Determination of the azo-hydrazono tautomerism of some 2-pyrazolin-5-onedyes by means of nuclear magnetic resonance spectroscopy and 15N-labeled compounds, J. Org. Chem. 34 (1969) 1685-1686.
-
[16]
[16] F.A. Snavely, C.H. Yoder, A study of tautomerism in arylazopyrazolones and related heterocycles with nuclear magnetic resonance spectroscopy, J. Org. Chem. 33 (1968) 513-515.
-
[17]
[17] C.H. Yoder, R.C. Barth, W.M. Richter, F.A. Snavely, A nuclear magnetic resonance study of some nitrogen-15 substituted azo heterocycles, J. Org. Chem. 37 (1972) 4121-4123.
-
[18]
[18] A.S. Shawali, N.M.S. Harb, K.O. Badahdah, A study of tautomerism in diazonium couplingproductsof 4-hydroxy coumarin, J.Heterocycl.Chem.22(1985)1397-1403.
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