Aryl azo 5-arylidene-2,4-thiazolidinone dyes as novel antioxidant and antibacterial compounds

Journal: Vol.8, No.2, 2015 - Article 5   Pages :  145 Until 152

Article Code:

A. Mohammadi: Faculty of Sciences, University of Guilan - Department of Chemistry
Hossien Ghafoori: University of Guilan - Department of Chemistry
Mehdi Rassa: University of Guilan - Department of Biology
Mastaneh Safarnejad: University of Guilan - Department of Chemistry

Article's abstract:

In the present study, nine bis-azo dyes based on 5-arylidene-2,4-thiazolidinone were obtained in two steps, using Knoevenagel condensation and azo coupling reactions. The structure of the dyes was confirmed on the basis of spectral data. Analysis of spectroscopic data shows that there is equilibrium between the azo and hydrazone tautomers for all dyes in solutions. Investigation of antioxidant activity of compounds was carried out by 2,2-dipheny l-1-picrylhydrazyl DPPH and ferric reducing antioxidant power FRAP methods. The antibacterial activity towards three Gram negative and two Gram positive bacteria was also investigated. The activity data show that the synthesized dyes 3a-i have promising antibacterial activity, comparable with their precursor 1.

Azo dye; 2,4-thiazolidinone; Tautomerism; Antioxidant activity; Antibacterial activity

1. C. Y. Hung, G. C. Yen, Antioxidant activity of phenolic compounds isolated from Mesona procumbens Hemsl, J. Agric. Food Chem., 50(2002), 2993-2997.#2. S. Koppireddi, J. R. Komsani, S. Avula, S. Pombala, S. Vasamsetti, S. Kotamraju, R. Yadla, Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds, Eur. J. Med. Chem., 66(2013), 305-313.#3. M. Valko, D. Leibfritz, J. Moncol, M. T. D. Cronin, M. Mazur, j. Telser, Free radicals and antioxidants in normal physiological functions and human disease, Int. J. Biochem. Cell Biol., 39(2007), 44-84.#4. J. P. Ye, Challenges in drug discovery for thiazolidinedione substitute, Acta Pharm. Sin. B., 1(2011), 137-142.#5. V. S. Jain, D. K. Vora, C. S. Ramaa, Thiazolidine-2,4-diones: Progress towards multifarious applications, Bioorg. Med. Chem., 21(2013), 1599-1620.#6. A. K. Jain, A. Vaidya, V. Ravichandran, S. K. Kashaw, R. K. Agrawal, Recent developments and biological activities of thiazolidinone derivatives, A review., Bioorg. Med. Chem., 20(2012), 3378-3395.#7. K. Omar, A. Geronikaki, P. Zoumpoulakis, C. Camoutsis, M. Sokovic, A. Ciric, J. Glamoclija, Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs, Bioorg. Med. Chem., 18(2010), 426-432.#8. G. Neves, R. Menegatti, C. B. Antonio, L. R. Grazziottin, R. O. Vieira, S. M. K. Rates, F. Noel, E. J. Barreiro, C. A. M. Fraga, Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors, Bioorg. Med. Chem., 18(2010), 1925-1935.#9. O. Zvarec, S. W. Polyak, W. Tieu, K. Kuan, H. Dai, D. S. Pedersen, R. Morona, L. Zhang, G. W. Booker, A. D. Abell, 5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials, Bioorg. Med. Chem. Lett., 22(2012), 2720-2722.#10. V. Patil, K. Tilekar, S. Mehendale-Munj, R. Mohan, C. S. Ramaa, Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2,4-thiazolidinedione derivatives, Eur. J. Med. Chem., 45(2010), 4539-4544.#11. W. H. W. Tang, G. S. Francis, B. J. Hoogwerf, J. B. Young, Fluid Retention After Initiation of Thiazolidinedione Therapy in Diabetic Patients With Established Chronic Heart Failure, J. Am. Coll. Cardiol., 41(2003), 1394-1398.#12. J. Griffiths, Photochemistry of azobenzene and its derivatives, A review., Chem. Soc. Rev., 1(1972), 481-493.#13. S. Bellotto, R. Reuter, C. Heinis, H. A. Wegner, Synthesis and Photochemical Properties of Oligo-ortho-azobenzenes, J. Org. Chem., 76(2011), 9826-9834.#14. J. Y. Park, Y. Hirata, K. Hamada, Relationship between the dye/additive interaction and inkjet ink droplet formation, Dyes Pigm., 95(2012), 502-511.#15. Y. D. Kim, J. H. Cho, C. R. Park, J. H. Choi, C. Yoon, J. P. Kim, Synthesis, application and investigation of structure–thermal stability relationships of thermally stable water-soluble azo naphthalene dyes for LCD red color filters, Dyes Pigm., 89(2011), 1-8.#16. H. S. Freeman, A. T. Peters, Colorants for Non-Textile Applications, Elsevier, 2000, 1-34.#17. D. H. Song, H. Y. Yoo, J. P. Kim, Synthesis of stilbene-based azo dyes and application for dichroic materials in poly(vinyl alcohol) polarizing films, Dyes Pigm., 75(2007), 727-731.#18. D. M. Marmion, Handbook of US. Colorants, third ed., John Wiley and Sons, Inc., New York, 1991.#19. G. Rosenfelder, J. Y. Chang, D. J Braun, Sphingosine determination at the picomole level using dimethylaminoazobenzene sulphonyl chloride, J. Chromatogr. B: Biomed. Sci. App., 272(1983), 21-27.#20. W. Huang, Y. Li, H. Lin, Colorimetric recognition of acetate anions in aqueous solution using charge neutral azo derivatives, Spectrochim. Acta A., 86(2012), 437-442.#21. E. Mohajerani, N. Hosain-Nataj, Studying the temperature dependence of the laser induced birefringence in azo dye doped polymer films, Opt. Mater., 29(2007), 1408-1415.#22. N. Hosain-Nataj, E. Mohajerani, H. Nemati, A. Moheghi, M. R. Yazdanbakhsh, M. Goli, A. Mohammadi, Studying optical and nonlinear optical properties of synthesized azo dyes doped in polymer and liquid crystal using birefringence and Z- scan techniques, J. Appl. Polym. Sci., 127(2013), 456-462.#23. F. Chami, M. R. Wilson, Molecular Order in a Chromonic Liquid Crystal: A Molecular Simulation Study of the Anionic Azo Dye Sunset Yellow, J. Am. Chem. Soc., 132(2010), 7794-7802.#24. A. Mohammadi, M. R. Yazdanbakhsh, L. Farahnak, Synthesis and evaluation of changes induced by solvent and substituent in electronic absorption spectra of some azo disperse dyes, Spectrochim. Acta A., 89(2012), 238-242. 25. M. R. Yazdanbakhsh, A. Mohammadi, Synthesis, substituent effects and solvatochromic properties of some disperse azo dyes derived from N-phenyl-2, 2′-iminodiethanol, J. Mol. Liq., 148(2009), 35-39. 26. A. Mohammadi, M. Safarnejad, Synthesis, structural characterization and tautomeric properties of some novel bis-azo dyes derived from 5-arylidene-2,4-thiazolidinone, Spectrochim. Acta A., 126(2014), 105-111. 27. E. J. Baron, S. M. Finegold, Bailey and Scotts’s diagnostic microbiology, 8th Ed.,Philadelphia. Toronto, 1990, 363-407.

Article's file
Page view: 3027
Article's download quantity : 55

Article System Login

Prof. Zahra Ranjbar
Dr. Farahnaz Nourmohammadian
Assistant Editor:
Dr. Mozhgan Hosseinnezhad
ISSN (online):
Institute for Color Science and Technology (ICST)

Quick Access
What is your opinion about the manuscript subscription system of PCCC website?
Website Statistics
Page view:3,028
Online Visitors:52