Skip to main content
SpringerLink
Log in

Ultrasound-Assisted Synthesis of Some Novel 1,3-Diarylpyrazolyl α-Aminophosphonates Conjugated with Nitrogen Heterocycles as Antifungal Agents using CdI2 Nanoparticles as an Efficient Catalyst

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Some novel 1,3-diarylpyrazolyl α-aminophosphonates conjugated with nitrogen heterocycles were synthesized via one-pot three-component reaction of 1,3-diaryl-1H-pyrazole-4-carbaldehydes, N-amino hetero­cycles, and diethyl phosphonate in the presence of CdI2 nanoparticles as an efficient catalyst under conventional heating at 80°C or ultrasonic (US) irradiation at 50°C. The latter protocol has essential advantages such as operational simplicity and excellent yields. The antifungal properties of the synthesized compounds were evaluated. Most of them showed excellent inhibitory activity against plant pathogenic fungi in comparison to propiconazole as reference fungicide.

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

Scheme
Scheme
Scheme
Fig. 1.
Fig. 2.
Scheme

REFERENCES

  1. Gavrilescu, M., Eng. Life Sci., 2005, vol. 5, p. 497. https://doi.org/10.1002/elsc.200520098

    Article  CAS  Google Scholar 

  2. Pogăcean, M.O. and Gavrilescu, M., Environ. Eng. Manage. J., 2009, vol. 8, p. 608. https://doi.org/10.30638/eemj.2009.084

    Article  Google Scholar 

  3. Orhan, D.D., Özçelik, B., Özgen, S., and Ergun, F., Microbiol. Res., 2010, vol. 165, p. 496. https://doi.org/10.1016/j.micres.2009.09.002

    Article  CAS  PubMed  Google Scholar 

  4. Thines, E., Heidrun, A., and Weber, R.W., Mycol. Res., 2004, vol. 108, p. 14. https://doi.org/10.1017/S0953756203008943

    Article  CAS  PubMed  Google Scholar 

  5. Sultatos, L.G., J. Toxicol. Environ. Health, Part A, 1994, vol. 43, p. 271. https://doi.org/10.1080/15287399409531921

    Article  CAS  Google Scholar 

  6. Malladi, S., Isloor, A., Peethambar, S.K., Ganesh, B.M., and Goud, P.S., Pharma Chem., 2012, vol. 4, p. 43. https://idr.nitk.ac.in/jspui/handle/123456789/13202

    CAS  Google Scholar 

  7. Koca, İ., Özgür, A., Coşkun, K.A., and Tutar, Y., Bioorg. Med. Chem., 2013, vol. 21, p. 3859. https://doi.org/10.1016/j.bmc.2013.04.021

    Article  CAS  PubMed  Google Scholar 

  8. Vijesh, A., Isloor, A.M., Shetty, P., Sundershan, S., and Fun, H.K., Eur. J. Med. Chem., 2013, vol. 62, p. 410. https://doi.org/10.1016/j.ejmech.2012.12.057

    Article  CAS  PubMed  Google Scholar 

  9. Kaushik, D., Khan, S.A., Chawla, G., and Kumar, S., Eur. J. Med. Chem., 2010, vol. 45, p. 3943. https://doi.org/10.1016/j.ejmech.2010.05.049

    Article  CAS  PubMed  Google Scholar 

  10. Gökhan-Kelekçi, N., Yabanoğlu, S., Küpeli, E., Salgın, U., Özgen, Ö., Uçar, G., Yeşilada, E., Kendi, E., Yeşilada, A., and Bilgin, A.A., Bioorg. Med. Chem., 2007, vol. 15, p. 5775. https://doi.org/10.1016/j.bmc.2007.06.004

    Article  CAS  PubMed  Google Scholar 

  11. Raffa, D., Maggio, B., Raimondi, M.V., Cascioferro, S., Plescia, F., Cancemi, G., and Daidone, G., Eur. J. Med. Chem., 2015, vol. 97, p. 732. https://doi.org/10.1016/j.ejmech.2014.12.023

    Article  CAS  PubMed  Google Scholar 

  12. El‐Kazak, A.M. and Ibrahim, M.A., J. Heterocycl. Chem., 2017, vol. 54, p. 1604. https://doi.org/10.1002/jhet.2749

    Article  CAS  Google Scholar 

  13. Siddiqui, A.A., Rajesh, R., Alagarsamy, V., and De Clercq, E., Arch. Pharm., 2007, vol. 340, p. 95. https://doi.org/10.1002/ardp.200600121

    Article  CAS  Google Scholar 

  14. Bhardwaj, N., Pathania, A., and Kumar, P., Curr. Tradit. Med., 2021, vol. 7, p. 5. https://doi.org/10.2174/2215083805666190613125700

    Article  CAS  Google Scholar 

  15. Demchenko, S., Lesyk, R., Yadlovskyi, O., Zuegg, J., Elliott, A.G., Drapak, I., Fedchenkova, Y., Suvorova, Z., and Demchenko, A., Molecules, 2021, vol. 26, article no. 4253. https://doi.org/10.3390/molecules26144253

  16. Demmer, C.S., Krogsgaard-Larsen, N., and Bunch, L., Chem. Rev., 2011, vol. 111, p. 7981. https://doi.org/10.1021/cr2002646

    Article  CAS  PubMed  Google Scholar 

  17. Reddy, M.V.N., Annar, S., Krishna, A.B., Reddy, G.C.S., and Reddy, C.S., Org. Commun., 2010, vol. 3, p. 39.

    CAS  Google Scholar 

  18. Thaslim Basha, S., Sudhamani, H., Rasheed, S., Venkateswarlu, N., Vijaya, T., and Naga Raju, C., Phosphorus, Sulfur Silicon Relat. Elem., 2016, vol. 191, p. 1339. https://doi.org/10.1080/10426507.2016.1192629

    Article  CAS  Google Scholar 

  19. Bhagat, S., Shah, P., Garg, S.K., Mishra, S., Kamal Kaur, P., Singh, S., and Chakraborti, A.K., MedChemComm, 2014, vol. 5, p. 665. https://doi.org/10.1039/C3MD00388D

    Article  CAS  Google Scholar 

  20. Valasani, K.R., Hu, G., Chaney, M.O., and Yan, S.S., Chem. Biol. Drug Des., 2013, vol. 81, p. 238. https://doi.org/10.1111/cbdd.12068

    Article  CAS  PubMed  Google Scholar 

  21. Sienczyk, M. and Oleksyszyn, J., Curr. Med. Chem., 2009, vol. 16, p. 1673. https://doi.org/10.2174/092986709788186246

    Article  CAS  PubMed  Google Scholar 

  22. Shaikh, S., Dhavan, P., Pavale, G., Ramana, M.M.V., and Jadhav, B.L., Bioorg. Chem., 2020, vol. 96, article ID 103589. https://doi.org/10.1016/j.bioorg.2020.103589

  23. Shady, A.A., Abu Bakr, S.M., and Khidre, M.D., J. Heterocycl. Chem., 2017, vol. 54, p. 71. https://doi.org/10.1002/jhet.2541

    Article  CAS  Google Scholar 

  24. Ali, T.E., Bakhotmah, D.A., Assiri, M.A., Yahia, I.S., and Zahran, H.Y., Russ. J. Org. Chem., 2021, vol. 57, p. 469. https://doi.org/10.1134/S1070428021030209

    Article  CAS  Google Scholar 

  25. Ali, T.E., Assiri, M.A., Abdel-Kariem, S.M., and Yahia, I.S., Heterocycles, 2021, vol. 102, p. 583. https://doi.org/10.3987/REV-20-941

    Article  CAS  Google Scholar 

  26. Rathelot, P., Azas, N., El-Kashef, H., Delmas, F., Di Giorgio, C., Timon-David, P., Maldonado, J., and Vanelle, P., Eur. J. Med. Chem., 2002, vol. 37, p. 671. https://doi.org/10.1016/S0223-5234(02)01388-0

    Article  CAS  PubMed  Google Scholar 

  27. El Gokha, A.A., Ghanim, I.M., Megeed, A.E.S.A., Shaban, E., and El Sayed, I.E.-T., Int. J. Pharm. Sci. Res., 2016, vol. 7, p. 181. https://doi.org/10.13040/IJPSR.0975-8232.7(1).181-89

    Article  CAS  Google Scholar 

  28. Kariper, İ.A., J. Mater. Res. Technol., 2016, vol. 5, p. 77. https://doi.org/10.1016/j.jmrt.2015.10.005

    Article  CAS  Google Scholar 

  29. Bozorth, R.M., J. Am. Chem. Soc., 1922, vol. 44, p. 2232. https://doi.org/10.1021/ja01431a019

    Article  CAS  Google Scholar 

  30. Jain, R. and Trigunayat, G., Acta Crystallogr., Sect. A, 1970, vol. 26, p. 463. https://doi.org/10.1107/S0567739470001237

    Article  CAS  Google Scholar 

  31. Tyagi, P., Vedeshwar, A., and Mehra, N., Phys. B (Amsterdam, Neth.), 2001, vol. 304, p. 166. https://doi.org/10.1016/S0921-4526(01)00392-1

    Article  CAS  Google Scholar 

  32. Charles, C., Martin, N., Devel, M., Ollitrault, J., and Billard, A., Thin Solid Films, 2013, vol. 534, p. 275. https://doi.org/10.1016/j.tsf.2013.03.004

    Article  CAS  Google Scholar 

  33. Rawat, R.S., Arun, P., Vedeshwar, A., Lee, P., and Lee, S., J. Appl. Phys., 2004, vol. 95, p. 7725. https://doi.org/10.1063/1.1738538

    Article  CAS  Google Scholar 

  34. Bekheet, A., Seyam, M., Sallam, F., and El-Shair, H., Eur. Phys. J.: Appl. Phys., 2000, vol. 11, p. 159. https://doi.org/10.1051/epjap:2000158

    Article  CAS  Google Scholar 

  35. Badadhe, P.V., Chavan, N.M., Ghotekar, D.S., Mandhane, P.G., Joshi, R.S., and Gill, C.H., Phosphorus, Sulfur Silicon Relat. Elem., 2011, vol. 186, p. 2021. https://doi.org/10.1080/10426507.2010.550268

    Article  CAS  Google Scholar 

  36. Devillers, J., Steiman, R., and Seigle-Murandi, F., Chemosphere, 1989, vol. 19, p. 1693. https://doi.org/10.1016/0045-6535(89)90512-2

    Article  CAS  Google Scholar 

Download references

Funding

The authors thank the deanship of scientific research at the King Khalid University for funding this work through research groups program under grant no. RGP.2/8/43.

Author information

Authors and Affiliations

  1. Pesticide Formulation Department, Central Agricultural Pesticide Laboratory, Agricultural Research Center, 12618, Dokki, Giza, Egypt

    M. Hussien & H. M. Torkey

  2. Department of Chemistry, Faculty of Science, Menoufia university, 32511, Shebin El-Kom, Egypt

    M. Hussien, I. E. El Sayed & A. H. Abdelaleem

  3. Department of Chemistry, Faculty of Science, King Khalid University, 61421, Abha, Saudi Arabia

    T. E. Ali & M. A. Assiri

  4. Department of Chemistry, Faculty of Education, Ain Shams University, 11711, Roxy, Cairo, Egypt

    T. E. Ali

  5. Department of Physics, Faculty of Education, Ain Shams University, 11711, Roxy, Cairo, Egypt

    I. S. Yahia

Authors
  1. M. Hussien
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. E. Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. E. El Sayed
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. H. Abdelaleem
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. H. M. Torkey
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. M. A. Assiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. I. S. Yahia
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. E. Ali.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hussien, M., Ali, T.E., Sayed, I.E.E. et al. Ultrasound-Assisted Synthesis of Some Novel 1,3-Diarylpyrazolyl α-Aminophosphonates Conjugated with Nitrogen Heterocycles as Antifungal Agents using CdI2 Nanoparticles as an Efficient Catalyst. Russ J Org Chem 59, 1214–1223 (2023). https://doi.org/10.1134/S1070428023070138

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428023070138

Keywords:

Search

Navigation