Skip to main content
Log in

Novel monoazo disperse and cationic dyes: preparation, structure investigation, study of spectroscopic, antibacterial and antifungal potential

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A series of azo naphthalimide dyes were prepared by coupling N,N-diethyl-m-toluidine with three heterocyclic amines as the diazo components. The structures of the nine prepared azo dyes were fully characterized by Fourier transform infrared, differential scanning calorimeter, thin-layer chromatography, proton and carbon nuclear magnetic resonance, mass spectrometry, elemental analysis (CHNS), and UV–Vis spectroscopic techniques. UV–Vis studies represented that all dyes have molar extinction coefficients between 30,000 and 61,000 M−1 cm−1 and have maximum wavelengths between 545 and 558 nm in DMF solution. The newly synthesized dyes were screened for their potential antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi using the cup plate and broth microdilution methods. The results of antibacterial and antifungal activities exhibited significant inhibitory effect against the test microorganisms in vitro.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Zhang YY, Zhou CH (2011) Bioorg Med Chem Lett 21:4349

    Article  CAS  PubMed  Google Scholar 

  2. Sk UH, Gowda ASP, Crampsie MA, Yun JK, Spratt TE, Amin S, Sharma AK (2011) Eur J Med Chem 46:3331

    Article  CAS  PubMed  Google Scholar 

  3. Hariprakasha HK, Kosakowska Cholody T, Meyer C, Cholody WM, Stinson SF, Tarasova NI, Michejda CJ (2007) J Med Chem 50:5557

    Article  CAS  PubMed  Google Scholar 

  4. Konstantinova TN, Miladinova PM (2009) J Appl Polym Sci 111:1991

    Article  CAS  Google Scholar 

  5. Damu Guri LV, Wang QP, Zhang ZH, Zhang YY, Lv JS, Zhou CH (2013) Sci China Chem 56:952

    Article  CAS  Google Scholar 

  6. Shaki H, Gharanjig K, Khosravi A (2015) Indian J Fibre Text 40:425

    CAS  Google Scholar 

  7. Lv JS, Peng XM, Kishore B, Zhou CH (2014) Bioorg Med Chem Lett 24:308

    Article  CAS  PubMed  Google Scholar 

  8. Horton JK, Wilson SH (2013) Mol Cancer Res 11:13

    Article  CAS  PubMed  Google Scholar 

  9. Grabchev I, Staneva D, Betcheva R (2012) Curr Med Chem 19:4976

    Article  CAS  PubMed  Google Scholar 

  10. Jeong Y, Yoon J (2012) Inorg Chim Acta 381:2

    Article  CAS  Google Scholar 

  11. Banerjee S, Veale EB, Phelan CM, Murphy SA, Tocci GM, Gillespie LJ, Frimannsson DO, Kelly JM, Gunnlaugsson T (2013) Chem Soc Rev 42:1601

    Article  CAS  PubMed  Google Scholar 

  12. Roger JE, Abraham B, Rostkowski A, Kelly LA (2001) Photochem Photobiol 74:521

    Article  Google Scholar 

  13. Kilpin J, Clavel CM, Edafe F, Dyson PJ (2012) Organometallics 31:7031

    Article  CAS  Google Scholar 

  14. Muth M, Hoerr V, Glaser M, Ponte-Sucre A, Moll H, Stich A, Holzgrabe U (2007) Bioorg Med Chem Lett 17:1590

    Article  CAS  PubMed  Google Scholar 

  15. Zhang YY, Mi JL, Zhou CH, Zhou XD (2011) Eur J Med Chem 46:4391

    Article  CAS  PubMed  Google Scholar 

  16. Abuo-Rahma GEDAA, Sarhan HA, Gad GFM (2009) Bioorg Med Chem 17:3879

    Article  CAS  Google Scholar 

  17. Duke RM, Veale EB, Pfeffer FM, Krugerc PE, Gunnlaugsson T (2010) Chem Soc Rev 39:3936

    Article  CAS  PubMed  Google Scholar 

  18. Brana MF, Castellano JM, Roldan CM, Santos A, Vazquez D, Jimenez A (1980) Cancer Chemother Pharm 4:61

    Article  CAS  Google Scholar 

  19. Stevenson KA, Yen SF, Yang NC, Boykin DW, Wilson WD (1984) J Med Chem 27:1677

    Article  CAS  PubMed  Google Scholar 

  20. Tao ZF, Qian XH, Wei D (1996) Dyes Pigm 31:245

    Article  CAS  Google Scholar 

  21. Li ZG, Yang Q, Qian XH (2005) Bioorg Med Chem 13:4864

    Article  CAS  PubMed  Google Scholar 

  22. Chen Z, Liang X, Zhang H, Xie H, Liu J, Xu Y, Zhu W, Wang Y, Wang X, Tan S, Kuang D, Qian XH (2010) J Med Chem 53:2589

    Article  CAS  PubMed  Google Scholar 

  23. Kamal A, Satyanarayana M, Devaiah V, Rohini V, Yadav JS, Mullickm B, Nagaraja V (2006) Lett Drug Des Discov 3:494

    Article  CAS  Google Scholar 

  24. Peters AT, Bide MJ (1986) Dyes Pigm 7:237

    Article  CAS  Google Scholar 

  25. Shaki H, Gharanjig K, Rouhani S, Khosravi A, Fakhar J (2012) Color Technol 128:270

    Article  CAS  Google Scholar 

  26. Shaki H, Gharanjig K, Rouhani S, Khosravi A (2010) J Photochem Photobiol A 216:44

    Article  CAS  Google Scholar 

  27. Dodangeh M, Gharanjig K, Arami M (2014) IEEE Sensor J 14:2889

    Article  CAS  Google Scholar 

  28. Safabakhsh B, Khosravi A, Gharanjig K, Kowsari E, Khorassani M, Tafaghodi S (2012) Color Technol 128:218

    Article  CAS  Google Scholar 

  29. Shaki H, Gharanjig K, Khosravi A (2015) Biotechnol Progr 31:1086

    Article  CAS  Google Scholar 

  30. Sharshira EM, Hamada NMM (2012) Am J Org Chem 2:69

    Article  CAS  Google Scholar 

  31. Luo YL, Baathulaa K, Kannekanti VK, Zhou CH, Cai GX (2015) Sci China Chem 58:483

    Article  CAS  Google Scholar 

  32. Moanta A, Ionescu C, Dragoi M, Tutunaru B, Rotaru P (2015) J Therm Anal Calorim 120:1151

    Article  CAS  Google Scholar 

  33. Salmon AJ, Williams ML, Wu QK, Morizzi J, Gregg D, Charman SA, Vullo D, Supuran CT, Poulson SA (2012) J Med Chem 55:5506

    Article  CAS  PubMed  Google Scholar 

  34. Sayed AZ, El-Gaby MSA (2001) Color Technol 117:293

    Article  CAS  Google Scholar 

  35. Shaki H, Khosravi A, Gharanjig K, Mahboubi A (2016) Mater Technol 31:322

    CAS  Google Scholar 

  36. Wojciechowski K (1993) Dyes Pigm 22:117

    Article  CAS  Google Scholar 

  37. Kose M, Kurtoglu N, Gumussu O, Tutak M, McKee V, Karakas D, Kurtoglu M (2013) J Mol Struct 1053:89

    Article  CAS  Google Scholar 

  38. Ebead YH (2011) Dyes Pigm 92:705

    Article  CAS  Google Scholar 

  39. Velasco MI, Kinen CO, De Rossi RH, Rossi LI (2011) Dyes Pigm 90:259

    Article  CAS  Google Scholar 

  40. Wojciechowski K (1990) Dyes Pigm 12:273

    Article  CAS  Google Scholar 

  41. Wojcicchowski K (1997) Dyes Pigm 33:149

    Article  Google Scholar 

  42. Griffiths J (1984) Developments in the chemistry and technology of organic dyes. Blackwell Scientific Publications, London

    Google Scholar 

  43. Liu S, Ma J, Zhao D (2007) Dyes Pigm 75:255

    Article  CAS  Google Scholar 

  44. Keerthi Kumar CT, Keshavayya J, Rajesh T, Peethambar SK, Shoukat Ali RA (2013) Chem Sci Trans 2:1346

    Google Scholar 

  45. Fazly Bazzaz BS, Khajehkaramadin M, Shokooheizadeh HR (2005) Iran J Pharm Res 4:87

    Google Scholar 

  46. Clinical and Laboratory Standards Institute (2006) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard, 7th edn, p 14

Download references

Acknowledgments

The author is grateful to the Golestan University. This work was supported by the Golestan University (project No. 961527).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hanieh Shaki.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shaki, H. Novel monoazo disperse and cationic dyes: preparation, structure investigation, study of spectroscopic, antibacterial and antifungal potential. Monatsh Chem 149, 1149–1160 (2018). https://doi.org/10.1007/s00706-017-2130-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-017-2130-6

Keywords

Navigation