Skip to main content
SpringerLink
Log in

Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

For the first time, quinazolin-4(3H)-one-based cationic surfactants were prepared and fully characterized by IR and NMR spectroscopic techniques and elemental analysis. Some of their physicochemical properties, such as density, critical micelle concentration, surface tension, effectiveness in surface tension reduction, Gibbs free energy of micellization, foam and emulsion stability, and anticorrosion activity were determined. Antibacterial and antifungal activities of the synthesized compounds were investigated. N,N-Dimethyl-N-{2-[(2-methyl-4-oxoquinazolin-3(4H)-yl)amino]-2-oxoethyl}tetradecan-1-aminium chloride (4a) showed the highest antibacterial activity against five human pathogens. Antifungal activity against Candida albicans was shown only by surfactant 4a.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. I. Khan, S. Zaib, S. Batool, N. Abbas, Z. Ashraf, J. Iqbal, A. Saeed, Bioorg. Med. Chem., 2016, 24, 2361.

    Article  CAS  PubMed  Google Scholar 

  2. B. K. Tiwary, K. Kiran Pradhan, A. K. Nanda, R. Chakraborty, J. Chem. Biol. Ther., 2015, 1, 1000104.

    Google Scholar 

  3. F. Alexandre, A. Berecibar, R. Wrigglesworth, T. Besson, Tetrahedron, 2003, 59, 1413.

    Article  CAS  Google Scholar 

  4. J. B. Jiang, D. P. Hesson, B. A. Dusak, D. L. Dexter, G. L. Kang, E. Hamel, J. Med. Chem., 1990, 33, 1721.

    Article  CAS  PubMed  Google Scholar 

  5. I. Nouira, I. K. Kostakis, C. Dubouilh, E. Chosson, M. Iannelli, T. Besson, Tetrahedron Lett., 2008, 49, 7033.

    Article  CAS  Google Scholar 

  6. K. Girij a, P. Selvam, G. Nagarajan, M. Chandramohan, Asian J. Chem., 2005, 17, 1111.

    CAS  Google Scholar 

  7. R. S. Giri, H. M. Thaker, T. Giordano, B. Chen, S. Nuthalapaty, K. K. Vasu, V. Sudarsanam, Eur. J. Med. Chem., 2010, 45, 3558.

    Article  CAS  PubMed  Google Scholar 

  8. H. A. Abuelizz, M. Marzouk, H. Ghabbour, R. Al-Salahi, Saudi Pharm. J., 2017, 25, 1047.

    Article  PubMed  PubMed Central  Google Scholar 

  9. R. R. Dangi, N. Hussain, A. Joshi, G. Pemawat, G. L. Talesara, Indian J. Chem., 2011, 50B, 1165.

    CAS  Google Scholar 

  10. N. C. Desai, A. M. Dodiya, P. N. Shihora, Med. Chem. Res., 2012, 21, 1577.

    Article  CAS  Google Scholar 

  11. G. Saravanan, V. Alagarsamy, C. R. Prakash, Med. Chem. Res., 2013, 22, 340.

    Article  CAS  Google Scholar 

  12. V. K. Pandey, L. P. Pathak, S. K. Mishra, Indian J. Chem., 2005, 44B, 1940.

    CAS  Google Scholar 

  13. V. Alagarsamy, V. R. Salomon, G. Vanikavitha, V. Paluchamy, M. R. Chandran, A. A. Sujin, A. Thangathiruppathy, S. Amuthalakshmi, R. Revathi, Biol. Pharm. Bull., 2002, 25, 1432.

    Article  CAS  PubMed  Google Scholar 

  14. V. Alagarsamy, G. Muruganthan, R. Venkateshperumal, Biol. Pharm. Bull., 2003, 26, 1711.

    Article  CAS  PubMed  Google Scholar 

  15. B. A. Rather, T. Raj, A. Reddy, M. P. S. Ishar, S. Sivakumar, P. Paneerselvam, Arch. Pharm. Chem. Life Sci., 2010, 343, 108.

    CAS  Google Scholar 

  16. M. M. Aly, Y. A. Mohamed, K. A. M. El-Bayouki, W. M. Basyouni, S. Y. Abbas, Eur. J. Med. Chem., 2010, 45, 3365.

    Article  CAS  PubMed  Google Scholar 

  17. D. Gupta, R. Kumar, R. K. Roy, A. Sharma, I. Ali, Md. Shamsuzzaman, Med. Chem. Res., 2013, 22, 3282.

    Article  CAS  Google Scholar 

  18. S. T. Al-Rashood, I. A. Aboldahab, M. N. Nagi, L. A. Abouzeid, A. A. M. Abdel-Aziz, S. G. Abdel-Hamide, K. M. Youssef, A. M. Al-Obaid, H. I. El-Subbagh, Bioorg. Med. Chem., 2006, 14, 8608.

    Article  CAS  PubMed  Google Scholar 

  19. S. E. Abbas, F. F. Barsoum, H. H. Georgey, E. R. Mohammed, Bull. Fac. Pharm. (Cairo Univ.), 2013, 51, 273.

    Google Scholar 

  20. S. Saravanan, P. Selvam, S. Kumar, E. D. Clercq, Int. J. Pharm. Pharm. Sci., 2010, 2, 71.

    CAS  Google Scholar 

  21. S. K. Krishnan, S. Ganguly, R. Veerasamy, B. Jan, Eur. Rev. Med. Pharmacol. Sci., 2011, 15, 673.

    CAS  PubMed  Google Scholar 

  22. A. J. Kh. Atia, S. S. Al-Mufrgeiy, Am. J. Chem., 2012, 2, 150.

    Article  Google Scholar 

  23. M. Hrast, K. Rozman, M. Jukic, D. Patin, S. Gobec, M. Sova, Bioorg. Med. Chem. Lett., 2017, 27, 3529.

    Article  CAS  PubMed  Google Scholar 

  24. S. Öztürk, Prot. Met. Phys. Chem. S., 2017, 53, 920.

    Article  Google Scholar 

  25. S. Öztürk, Russ. J. Org. Chem., 2019, 55, 245.

    Article  Google Scholar 

  26. R. El-Sayed, A. A. F. Wasfy, A. A. Aly, J. Heterocycl. Chem., 2005, 42, 125.

    Article  CAS  Google Scholar 

  27. A. M. F. Eissa, Grasas Aceites, 2007, 58, 379.

    CAS  Google Scholar 

  28. A. M. F. Eissa, R. El-Sayed, Grasas Aceites, 2007, 58, 20.

    CAS  Google Scholar 

  29. H. Varshney, A. Ahmad, A. Rauf, F. M. Husain, I. Ahmad, J. Saudi Chem. Soc., 2017, 21, S394.

    Article  CAS  Google Scholar 

  30. M. A. Al-Omar, A. S. El-Azab, H. A. El-Obeid, S. G. A. Hamide, J. Saudi Chem. Soc., 2006, 10, 111.

    Google Scholar 

  31. S. Öztürk, A. Yıldırım, G. Gece, H. Türkdemir, J. Surfact. Deterg., 2019, 22, 197.

    Article  CAS  Google Scholar 

  32. S. Sugden, J. Chem. Soc. Trans., 1921, 119, 1483.

    Article  CAS  Google Scholar 

  33. W. Martino, J. Fernandez de la Mora, Y. Yoshida, G. Saito, J. Wilkes, Green Chem., 2006, 8, 390.

    Article  CAS  Google Scholar 

  34. M. A. El-Sukkary, A. A. El-Sawy, F. El-Dib, Hung. J. Ind. Chem., 1987, 15, 317.

    CAS  Google Scholar 

  35. E. Kuliszewska, L. Brecker, J. Surfact. Deterg., 2014, 17, 951.

    Article  CAS  Google Scholar 

  36. N. A. Negm, A. S. Mohamed, J. Surfact. Deterg., 2004, 7, 23.

    Article  CAS  Google Scholar 

  37. German version EN 10130:2006, Deutsches Institut für Normunge, Berlin, 2007, 14.

  38. G. E. Burrows, R. J. Morton, W. H. Fales, J. Vet. Diagn. Invest., 1993, 5, 541.

    Article  CAS  PubMed  Google Scholar 

  39. P. Tyagi, R. Tyagi, Eur. J. Lipid Sci. Technol., 2011, 113, 848.

    Article  CAS  Google Scholar 

  40. K. Taleb, M. M. Benkada, N. Benhamed, S. S. Besbes, Y. Grohens, A. Derdour, J. Mol. Liq., 2017, 241, 81.

    Article  CAS  Google Scholar 

  41. L. H. Lin, C. C. Wang, K. M. Chen, P. C. Lin, Colloids Surf. A., 2013, 436, 881.

    Article  CAS  Google Scholar 

  42. I. Aiad, M. M. El-Sukkary, E. A. Soliman, M. Y. El-Awady, S. M. Shaban, J. Ind. Eng. Chem., 2014, 20, 1633.

    Article  CAS  Google Scholar 

  43. S. G. Oh, D. O. Shah, J. Am. Oil Chem. Soc., 1993, 70, 673.

    Article  CAS  Google Scholar 

  44. L. Wang, H. Qin, L. L. Ding, S. Huo, Q. Deng, B. Zhao, L. Meng, T. Yan, J. Surfact. Deterg., 2014, 17, 1099.

    Article  CAS  Google Scholar 

  45. Y. Bao, J. Guo, J. Ma, M. Li, X. Li, J. Mol. Liq., 2017, 242, 8.

    Article  CAS  Google Scholar 

  46. E. Jafari, M. R. Khajouei, F. Hassanzadeh, G. H. Hakimelahi, G. A. Khodarahmi, Res. Pharm. Sci., 2016, 11, 1.

    PubMed  PubMed Central  Google Scholar 

  47. A. Kumar, P. Sharma, P. Kumari, B. L. Kalal, Bioorg. Med. Chem. Lett., 2011, 21, 4353.

    Article  CAS  PubMed  Google Scholar 

  48. M. A. Abd-Elhakeem, A. M. Elsayed, J. Chem. Pharm. Res., 2013, 5, No. 5, 275.

    CAS  Google Scholar 

  49. G. Saravanan, V. Alagarsamy, C. R. Prakash, J. Saudi Chem. Soc., 2015, 19, 3.

    Article  Google Scholar 

  50. M. B. Deshmukh, S. Patil, S. S. Patil, S. D. Jadhav, Indian J. Pharm. Sci., 2010, 72, 500.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  51. Y. Murti, A. K. Singh, D. Pathak, Indian J. Pharm. Sci., 2011, 73, 333.

    CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Bursa Uludağ University, Bursa, 16059, Turkey

    S. Öztürk & A. Yıldırım

  2. Department of Biology, Çankırı Karatekin University, Çankırı, 18100, Turkey

    S. Okay

  3. Vaccine Institute, Hacettepe University, Ankara, 06230, Turkey

    S. Okay

Authors
  1. S. Öztürk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Okay
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Yıldırım
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. Öztürk.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2205—2214, November, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Öztürk, S., Okay, S. & Yıldırım, A. Synthesis, anticorrosion, antibacterial, and antifungal activity of new amphiphilic compounds possessing quinazolin-4(3H)-one scaffold. Russ Chem Bull 69, 2205–2214 (2020). https://doi.org/10.1007/s11172-020-3023-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-3023-0

Key words

Search

Navigation