Skip to main content
SpringerLink
Log in

A Simple Process for the Synthesis of Novel Pyrazolyltriazole and Dihydropyrazolylthiazole Derivatives as Antimicrobial Agents

  • Research Article - Chemistry
  • Published:
Arabian Journal for Science and Engineering Aims and scope Submit manuscript

Abstract

Series of novel 1,2-bis((3-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazines 4 and 2-(5-(3-(1,2,3-triazol-4-yl)pyrazol-4-yl) pyrazol-1-yl)thiazoles 13 were synthesized using simple and convenient procedures, and their structures were established. Treatment of pyrazole-4-carbaldehydes 1 with methyl ketones in alkaline medium gave the corresponding (E)-1-aryl-3-(3-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones 3 in 82–86% yields. Treatment of 3 with hydrazine hydrate gave 4, in 69–75% yields, rather than the expected 1-aryl-5-methyl-4-(1-aryl-4-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-1H-pyrazol-3-yl)-1H-1,2,3-triazoles. Reactions of 3 with thiosemicarbazide gave the corresponding carbothioamides 9 which in reaction with phenacyl bromides gave the corresponding dihydropyrazolylthiazoles 13 in 82–87% yields. The novel synthesized product exhibits good antimicrobial activities against the tested microorganisms.

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. Bhat, M.; Nagaraja, G.K.; Kayarmar, R.; Peethamber, S.K.; Shafeeulla, R.M.: Design, synthesis and characterization of new 1,2,3-triazolyl pyrazole derivatives as potential antimicrobial agents via a Vilsmeier–Haack reaction approach. RSC Adv. 6, 59375–59388 (2016)

    Article  Google Scholar 

  2. Gouda, M.A.; Abu-Hashem, A.A.; Saad, M.H.; Elattar, K.M.: 5-Chloropyrazole-4-carboxaldehydes as synthon in heterocyclic synthesis. Res. Chem. Int. 42, 2119–2162 (2016)

    Article  Google Scholar 

  3. Havrylyuk, D.; Roman, O.; Lesyk, R.: Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazolineethiazolidine-based hybrids. Eur. J. Med. Chem. 113, 145–166 (2016)

    Article  Google Scholar 

  4. Abdel-Wahab, B.F.; Khidre, R.E.; Farahat, A.A.: Pyrazole-3(4)-carbaldehyde: synthesis, reactions and biological activity. Arkivoc I, 196–245 (2011)

    Google Scholar 

  5. Panda, N.; Jena, A.K.: Fe-catalyzed one-pot synthesis of 1,3-di- and 1,3,5-trisubstituted pyrazoles from hydrazones and vicinal diols. J. Org. Chem. 77, 9401–9406 (2012)

    Article  Google Scholar 

  6. Schmitt, D.C.; Taylor, A.P.; Flick, A.C.; Kyne Jr., R.E.: Synthesis of pyrazoles from 1,3-diols via hydrogen transfer catalysis. Org. Lett. 17, 1405–1408 (2015)

    Article  Google Scholar 

  7. Wu, L.-L.; Ge, Y.-C.; He, T.; Zhang, L.; Fu, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X.: An efficient one-pot synthesis of 3,5-disubstituted \(1H\)-pyrazoles. Synthesis 44, 1577–1583 (2012)

    Article  Google Scholar 

  8. Specklin, S.; Decuypere, E.; Plougastel, L.; Aliani, S.; Taran, F.: One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone–alkyne cycloaddition reaction. J. Org. Chem. 79, 7772–7777 (2014)

    Article  Google Scholar 

  9. Reddy, C.R.; Vijaykumar, J.; Grée, R.: Facile one-pot synthesis of 3,5-disubstituted 1\(H\)-pyrazoles from propargylic alcohols via propargyl hydrazides. Synthesis 45, 830–836 (2013)

    Article  Google Scholar 

  10. Harigae, R.; Moriyama, K.; Togo, H.: Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine. J. Org. Chem. 79, 2049–2058 (2014)

    Article  Google Scholar 

  11. Heller, S.T.; Natarajan, S.R.: 1,3-Diketones from acid chlorides and ketones: a rapid and general one-pot synthesis of pyrazoles. Org. Lett. 8, 2675–2678 (2008)

    Article  Google Scholar 

  12. Gosselin, F.; O’Shea, P.D.; Webster, R.A.; Reamer, R.A.; Tillyer, R.D.; Grabowski, E.J.J.: Highly regioselective synthesis of 1-aryl-3,4,5-substituted pyrazoles. Synlett 3267–3270 (2006). doi:10.1055/s-2006-956487

  13. Distinto, R.; Zanato, C.; Montanari, S.; Cascio, M.G.; Lazzari, P.; Pertwee, R.; Zanda, M.: Pyrazoles with a “click” 4-[\(N\)-(4-fluorobutyl)-1,2,3-triazole] substituent in position 3 are nanomolar \(\text{ CB }_{1}\) receptor ligands. J. Fluor. Chem. 167, 184–191 (2014)

    Article  Google Scholar 

  14. Abdel-Wahab, B.F.; Abdel-Latif, E.; Mohamed, H.A.; Awad, G.E.A.: Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents. Eur. J. Med. Chem. 52, 263–268 (2012)

    Article  Google Scholar 

  15. Kaur, K.; Kumar, V.; Beniwal, V.; Kumar, V.; Aneja, K.R.; Sharma, V.; Jaglan, S.: Solvent-free synthesis of novel (\(E)\)-2-(3,5-dimethyl-4-(aryldiazenyl)-1\(H\)-pyrazol-1-yl)-4-arylthiazoles: determination of their biological activity. Med. Chem. Res. 24, 3863–3875 (2015)

    Article  Google Scholar 

  16. Ye, L.; Dickerson, T.; Kaur, H.; Takada, Y.K.; Fujita, M.; Liu, R.; Knapp, J.M.; Lam, K.S.; Schore, N.E.; Kurth, M.J.; Takada, Y.: Identification of inhibitors against interaction between pro-inflammatory sPLA2-IIA protein and integrin \(\alpha \)v\(\beta 3\). Bioorg. Med. Chem. Lett. 23, 340–345 (2013)

    Article  Google Scholar 

  17. Patel, H.; Ugale, V.; Ingale, A.; Bari, S.: Synthesis and antimicrobial evaluation of pyrazo-thiazoles. Lett. Drug Des. Discov. 9, 840–847 (2012)

    Article  Google Scholar 

  18. Ye, L.; Knapp, J.M.; Sangwung, P.; Fettinger, J.C.; Verkman, A.S.; Kurth, M.J.: Pyrazolylthiazole as \(\Delta \)F508-cystic fibrosis transmembrane conductance regulator correctors with improved hydrophilicity compared to bithiazoles. J. Med. Chem. 53, 3772–3781 (2010)

    Article  Google Scholar 

  19. Baashen, M.A.; Abdel-Wahab, B.F.; El-Hiti, G.A.: Syntheses of triazoloquinoxalines. Heterocycles 92, 1931–1952 (2016)

    Article  Google Scholar 

  20. Bekheit, M.S.; Farahat, A.A.; Abdel-Wahab, B.F.: Synthetic routes to thiazoloquinazolines. Chem. Heterocycl. Compd. 52, 766–772 (2016)

    Article  Google Scholar 

  21. Smith, K.; Alotaibi, M.H.; El-Hiti, G.A.: Regioselective nitration of 2- and 4-nitrotoluenes over systems comprising nitric acid, an acid anhydride and a zeolite. Arkivoc V, 301–309 (2014)

    Google Scholar 

  22. Smith, K.; El-Hiti, G.A.; Al-Mansury, S.A.; Alshammari, M.B.; Balakit, A.A.: Lateral lithiation and substitution of \(N^{\prime }\)-(2-methylphenyl)-\(N{,}N\)-dimethylurea. Arkivoc V, 365–375 (2014)

    Google Scholar 

  23. El-Hiti, G.A.; Smith, K.; Hegazy, A.S.; Alshammari, M.B.; Masmali, A.: Directed lithiation of simple aromatics and heterocycles for synthesis of substituted derivatives. Arkivoc IV, 19–47 (2015)

    Google Scholar 

  24. Smith, K.; El-Hiti, G.A.; Hegazy, A.S.; Kariuki, B.M.: A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of \(N^{\prime }\)-benzyl-\(N{,}N\)-dimethylureas. Beilstein J. Org. Chem. 7, 1219–1227 (2011)

    Article  Google Scholar 

  25. Abdel-Wahab, B.F.; Mohamed, H.A.; Ali, M.M.: Synthesis and in vitro cytotoxicity of new 3-(5-methyl-1-aryl-1\(H\)-1,2,3-triazol-4-yl)-1-phenyl-1\(H\)-pyrazoles. J. Mod. Med. Chem. 3, 9–15 (2015)

    Article  Google Scholar 

  26. Pokhodylo, N.T.; Savka, R.D.; Matiichuk, V.S.; Obushak, N.D.: Synthesis and selected transformations of 1-(5-methyl-1-aryl-1\(H\)-1,2,3-triazol-4-yl)ethanones and 1-[4-(4-\(R\)-5-methyl-1\(H\)-1,2,3-triazol-1-yl)phenyl]ethanones. Russ. J. Gen. Chem. 79, 309–314 (2009)

    Article  Google Scholar 

  27. Balouiri, M.; Sadiki, M.; Ibnsouda, S.K.: Methods for in vitro evaluating antimicrobial activity: a review. J. Pharm. Anal. 6, 71–79 (2016)

    Article  Google Scholar 

  28. Scott, A.C.: Laboratory control of antimicrobial therapy. In: Collee, J.G., Duguid, J.P., Fraser, A.G., Marmion, B.P. (eds.) Mackie and McCartney Practical Medical Microbiology, vol. 2, 13th edn, pp. 161–181. Churchill Livingstone, Edinburgh (1989)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Applied Organic Chemistry Department, National Research Center, Dokki, Giza, 12622, Egypt

    Bakr F. Abdel-Wahab & Hanan A. Mohamed

  2. Department of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia

    Bakr F. Abdel-Wahab & Hanan A. Mohamed

  3. Chemical Industries Division, National Research Centre, Dokki, Giza, 12622, Egypt

    Rizk E. Khidre

  4. Chemistry Department, Faculty of Science, Jazan University, Jazan, Saudi Arabia

    Rizk E. Khidre

  5. Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, P.O. Box 10219, Riyadh, 11433, Saudi Arabia

    Gamal A. El-Hiti

Authors
  1. Bakr F. Abdel-Wahab
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rizk E. Khidre
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hanan A. Mohamed
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Gamal A. El-Hiti
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Bakr F. Abdel-Wahab or Gamal A. El-Hiti.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Abdel-Wahab, B.F., Khidre, R.E., Mohamed, H.A. et al. A Simple Process for the Synthesis of Novel Pyrazolyltriazole and Dihydropyrazolylthiazole Derivatives as Antimicrobial Agents. Arab J Sci Eng 42, 2441–2448 (2017). https://doi.org/10.1007/s13369-017-2530-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13369-017-2530-2

Keywords

Search

Navigation