Synthesis, Absorption Properties and Biological Evaluation of Some Novel Disazo Dyes Derived from Pyrazole Derivatives

Nesrin Sener; Izzet Sener; Serkan Yavuz; Fikret Karci

doi:10.14233/ajchem.2015.18769

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Issue Published : April 27, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Absorption Properties and Biological Evaluation of Some Novel Disazo Dyes Derived from Pyrazole Derivatives

https://doi.org/10.14233/ajchem.2015.18769

Nesrin Sener

Department of Chemistry, Faculty of Science-Arts, Pamukkale University, 20017 Denizli, Turkey

Izzet Sener

Department of Chemistry, Faculty of Science-Arts, Pamukkale University, 20017 Denizli, Turkey

Serkan Yavuz

Department of Chemistry, Faculty of Science, Gazi University, 06500 Ankara, Turkey

Fikret Karci

Department of Chemistry, Faculty of Science-Arts, Pamukkale University, 20017 Denizli, Turkey

Corresponding Author(s) : Nesrin Sener

nesrinburukoglu_sener@hotmail.com.tr

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8
Article Published : April 27, 2015

Abstract

In this study, 20 novel disazo dyes containing pyrazole derivatives were synthesized by a convenient method. Diazotized aniline and some aniline derivatives were reacted with malononitrile to give 2-arylazomalononitrile derivatives 1(a-e). The synthesized 2-arylazomalononitrile derivatives were reacted with hydrazine and phenyl hydrazine to afford the corresponding 3,5-diamino-4-arylazo-1H-pyrazole 2(a-e) and 3,5-diamino-4-arylazo-1-phenylpyrazole 3(a-e). Diazotized compounds of 2(a-e)and 3(a-e) reacted with ethylacetoacetate to give 4-arylazo-3-amino-1H-pyrazole-5-ylazo-ethylacetoacetate 4(a-e) and 4-arylazo-3-amino-1-phenylpyrazole-5-ylazo-ethylacetoacetate 7(a-e). The obtained 4(a-e) and 7(a-e) were reacted with hydrazine and phenyl hydrazine to give disazo dyes 5(a-e), 6(a-e), 8(a-e) and 9(a-e), respectively. The synthesized disazo dyes were characterized by spectroscopic techniques as well as elemental analysis. The solvatochromic behaviours of these dyes in various solvents were examined. Acid-base effects on the absorption maxima of the dyes were also reported. Antimicrobial activities of the synthesized novel disazo dyes were investigated.

Keywords

Pyrazolone Diazotization Solvatochromism Pyrazole Disazo dyes Antimicrobial activity

Sener, N., Sener, I., Yavuz, S., & Karci, F. (2015). Synthesis, Absorption Properties and Biological Evaluation of Some Novel Disazo Dyes Derived from Pyrazole Derivatives. Asian Journal of Chemistry, 27(8), 3003–3012. https://doi.org/10.14233/ajchem.2015.18769

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References

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References

H. Zollinger, Color Chemistry, Wiley-VCH: Weinheim, edn 3 (2003).

A. Pielesz, J. Mol. Struct., 511-512, 337 (1999); doi:10.1016/S0022-2860(99)00176-3.

M.R. Yazdanbakhsh, M. Abbasnia, M. Sheykhan and L. Ma’mani, J. Mol. Struct., 997, 266 (2010); doi:10.1016/j.molstruc.2010.06.005.

N. Junnarkar, D.S. Murty, N.S. Bhatt and D. Madamwar, World J. Microbiol. Biotechnol., 22, 163 (2006); doi:10.1007/s11274-005-9014-3.

N.A. Oranusi and C.J. Ogugbue, J. Appl. Sci. Environ. Manage., 9, 39 (2005).

A.T. Peters and E. Chisowa, Dyes Pigments, 22, 223 (1993); doi:10.1016/0143-7208(93)80015-S.

H. Hartmann, M. Schulze and R. Guenter, Dyes Pigments, 15, 255 (1991); doi:10.1016/0143-7208(91)80010-7.

U. Garg, V. Sareen, V. Khatri and S. Chaugh, Indian J. Heterocycl. Chem., 12, 139 (2002).

N.R. Thakare, A.K. Dhawas and P.S. Ganoskar, J. Chem. Pharm. Res., 4, 3329 (2012).

A.A. Bekhit and T. Abdel-Aziem, Bioorg. Med. Chem., 12, 1935 (2004); doi:10.1016/j.bmc.2004.01.037.

M. Amir, S.M. Hassan and A. Wadood, Oriental J. Chem., 18, 351 (2002).

Z. Tabarelli, M.A. Rubin, D.B. Berlese, P.D. Sauzem, T.P. Missio, M.V. Teixeira, A.P. Sinhorin, M.A.P. Martins, N. Zanatta, H.G. Bonacorso and C.F. Mello, Braz. J. Med. Biol. Res., 37, 1531 (2004); doi:10.1590/S0100-879X2004001000013.

S.K. Sahu, M. Banerjee, A. Samantray, C. Behera and M.A. Azam, Trop. J. Pharm. Res., 7, 961 (2008); doi:10.4314/tjpr.v7i2.14664.

A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, J.A. Micky and F.M.E. Abdel-Megeid, Bioorg. Med. Chem., 16, 7102 (2008); doi:10.1016/j.bmc.2008.06.054.

Ş.G. Kücükgüzel, S. Rollas, H. Erdeniz, M. Kiraz, A.C. Ekinci and A. Vidin, Eur. J. Med. Chem., 35, 761 (2000); doi:10.1016/S0223-5234(00)90179-X.

P.C. Tsai and I.J. Wang, Dyes Pigments, 64, 259 (2005); doi:10.1016/j.dyepig.2004.05.013.

M.H. Elnagdi, M.M.M. Sallam, H.M. Fahmy, S.A.M. İbrahim and M.A.M. Elias, Helv. Chim. Acta, 59, 551 (1976); doi:10.1002/hlca.19760590220.

M.H. Fanagdi, E.M. Kandeel, E.M. Zayed and Z.F. Kandil, J. Heterocycl. Chem., 14, 155 (1977); doi:10.1002/jhet.5570140132.

M.H. Elnagdi, S.M. Fahmy, E.A.Z. Hafez, M.R.H. Elmoghayar and S.A.R. Amer, J. Heterocycl. Chem., 16, 1109 (1979); doi:10.1002/jhet.5570160606.

A.C. Scott, in eds.: J.G. Collee, J.P. Duguid, A.G Fraser and B.P. Marmion, Laboratory Control of Antimicrobial Therapy, In: Mackie and McCartney Practical Medical Microbiology, Churchill Livingstone, edn 13, pp. 161-181 (1989).

A.H. Shamroukh, M.E.A. Zaki, E.M.H. Morsy, F.M. Abdel-Motti and F.M.E. Abdel-Megeid, Arch. Pharm. Chem. Life Sci., 340, 345 (2007); doi:10.1002/ardp.200700007.

F. Karci, A. Demirçali, I. Şener and T. Tilki, Dyes Pigments, 71, 90 (2006); doi:10.1016/j.dyepig.2005.06.006.

F. Karci and F. Karci, Dyes Pigments, 76, 147 (2008); doi:10.1016/j.dyepig.2006.07.029.

F. Karci, I. Şener, A. Demirçali and N. Burukoglu, Color. Technol., 122, 264 (2006); doi:10.1111/j.1478-4408.2006.00035.x.

F. Karci, N. Şener, M. Yamaç, I. Şener and A. Demirçali, Dyes Pigments, 80, 47 (2009); doi:10.1016/j.dyepig.2008.05.001.

C. Reichart and T. Welton, Solvent and Solvent Effect in Organic Chemistry, Wiley-VCH Verlag & Co. KgaA: Weinheim, edn 4 (2011).

L. Liu, Z. Ren, H. Li, H. Shang and J. Lang, Chin. J. Chem., 28, 1829 (2010); doi:10.1002/cjoc.201090306.

K.J. Jain, P.H. Kanaiya and N. Bhojak, Fib. Polym., 9, 720 (2008); doi:10.1007/s12221-008-0113-2.

U. Harikrishnan and S.K. Menon, Dyes Pigments, 77, 462 (2008); doi:10.1016/j.dyepig.2007.07.014.

F.I. Carroll and A. Sobti, J. Am. Chem. Soc., 95, 8512 (1973); doi:10.1021/ja00807a003.

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Synthesis, Absorption Properties and Biological Evaluation of Some Novel Disazo Dyes Derived from Pyrazole Derivatives

Corresponding Author(s) : Nesrin Sener

Abstract

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