JOURNAL OF THE CZECH PHARMACEUTICAL SOCIETY AND THE SLOVAK PHARMACEUTICAL SOCIETY

Čes. slov. farm. 2024, 73(3):E7-E12 | DOI: 10.36290/csf.2024.032

Novel pyrazole bearing heterocyclic hybrids as promising biologically active compounds

Kostiantyn Shabelnyk1, Yevhen Zaika2, Dmytro Skoryna1, Inna Nosulenko3, Anna Kinichenko3, Oleksii Voskoboinik4, Serhii Kovalenko5
1 Department of Pharmaceutical, Organic and Bioorganic chemistry, Zaporizhzhia State Medical and Pharmaceutical University, Mariia Pryimachenko av. 26, Zaporizhzhia, 69035, Ukraine.
2 Enamine Ltd, Kyiv, Ukraine, Winston Churchill st. 78, Kyiv, 02094 Ukraine.
3 Department of Pharmacognosy, Pharmacology and Botany, Zaporizhzhia State Medical and Pharmaceutical University, Zaporizhzhia, Ukraine, Mayakovski av. 26, Zaporizhzhia, 69035, Ukraine.
4 Department of Composite Materials, Chemistry and Technologies, National University „Zaporizhzhia Polytechnic“, Universytetska st. 64, Zaporizhzhia, 69063, Ukraine.
5 Research Institute of Chemistry and Geology, Oles Honchar Dnipro National University, Ukraine, 72, Nauky av., Dnipro, 49010, Ukraine.

The paper presents the results of a study devoted to the synthesis, evaluation of physicochemical properties, antiradical, and antimicrobial activity of pyrazole-containing heterocyclic hybrids. It has been shown that pyrazole bearing heterocyclic hybrids that contain quinazoline, triazoloquinazoline or triazole moieties are available via a series of reactions that include the interaction of 4-chloroquinazoline with pyrazole-containing hydrazides, cyclization of formed products into corresponding triazoloquinazolines, and hydrolytic cleavage of the electron-deficient tricyclic system. The structures of synthesized compounds have been verified by a complex of physicochemical methods, and the features of 1H NMR spectral characteristics have been described as well. The evaluation of obtained compounds’ biological activity revealed a moderate bacteriostatic effect against Pseudomonas aeruginosa and Candida albicans, as well as high radical scavenging activity of some of the studied heterocyclic hybrids.

Keywords: heterocyklické hybridy, pyrazol, chinazolin, triazol, antiradikálová aktivita

Accepted: September 23, 2024; Published: October 8, 2024  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Shabelnyk K, Zaika Y, Skoryna D, Nosulenko I, Kinichenko A, Voskoboinik O, Kovalenko S. Novel pyrazole bearing heterocyclic hybrids as promising biologically active compounds. Čes. slov. farm. 2024;73(3):E7-12. doi: 10.36290/csf.2024.032.
Download citation
PDF will be unlocked 8.10.2025

References

  1. Ebenezer O, Shapi M, Tuszynski JA. Review of the recent development in the synthesis and biological evaluations of pyrazole derivatives. Biomedicines. 2022;10:1124. doi:10.3390/biomedicines10051124. Go to original source... Go to PubMed...
  2. Sivaramakarthikeyan R, Iniyaval S, Saravanan V, et al. Molecular hybrids integrated with benzimidazole and pyrazole structural motifs: design, synthesis, biological evaluation, and molecular docking studies. ACS Omega. 2020;5:10089-98. doi:10.1021/acsomega.0c00630. Go to original source... Go to PubMed...
  3. Chavan RR, Hosamani KM. Microwave-assisted synthesis, computational studies, and antibacterial/anti-inflammatory activities of compounds based on coumarin-pyrazole hybrid. R. Soc. open sci. 2018;5:172435. doi:10.1098/rsos.172435. Go to original source... Go to PubMed...
  4. Kuthyala S, Sheikh S, Prabhu A, et al. Synthesis, characterization, and anticancer studies of some pyrazole-based hybrid heteroatomics. ChemistrySelect. 2020;5:10827-34. doi:10.1002/slct.202002483. Go to original source...
  5. Monteiro ME, Lechuga G, Lara LS, et al. Synthesis, structure-activity relationship and trypanocidal activity of pyrazole-imidazoline and new pyrazole-tetrahydropyrimidine hybrids as promising chemotherapeutic agents for Chagas' disease. Eur. J. Med. Chem. 2019;111610. doi:10.1016/j.ejmech.2019.111610. Go to original source... Go to PubMed...
  6. Desai NC, Bhatt K, Monapara J, et al. Conventional and microwave-assisted synthesis, antitubercular activity, and molecular docking studies of pyrazole and oxadiazole hybrids. ACS Omega. 2021;6:28270-84. doi:10.1021/acsomega.1c04411. Go to original source... Go to PubMed...
  7. Todorova A, Ivanova Y, Nedeva T, et al. Novel heterocyclic hybrids of pyrazole: synthesis and antifungal activity. Journal of chemical Technology and metallurgy. 2021; 56: 533-40.
  8. Gondru R, Sirisha K, Raj S, et al. Design, synthesis, in vitro evaluation and docking studies of pyrazole-thiazole hybrids as antimicrobial and antibiofilm agents. ChemistrySelect. 2018;3:8270-6. doi:10.1002/slct.201801391. Go to original source...
  9. Kumar P, Duhan M, Sindhu J, et al. Thiazolidine-4-one clubbed pyrazoles hybrids: Potent α-amylase and α-glucosidase inhibitors with NLO properties. J. Het. Chem. 2019;57:1573-87. doi:10.1002/jhet.3882. Go to original source...
  10. Pogaku V, Gangarapu K, Basavoju S, et al. Design, synthesis, molecular modelling, ADME prediction and anti-hyperglycemic evaluation of new pyrazole-triazolopyrimidine hybrids as potent α-glucosidase inhibitors. Bioorg. Chem. 2019;103307. doi:10.1016/j.bioorg.2019.103307. Go to original source... Go to PubMed...
  11. Jian FF, Wang J, Liang TL, Wang X. In situ synthesis of (5-phenyl-1H-pyrazole-3-carboxylic acid) metal complexes and their stable supramolecular microporous frameworks. Inorganica Chim. Acta. 2009;362:4219-25. doi:10.1016/j.ica.2009. 06. 039 Go to original source...
  12. Szabo M, Idiţoiu C, Chambre D, Lupea A. Improved DPPH determination for antioxidant activity spectrophotometric assay. Chem. Pap. 2007;61:214-6. doi:10.2478/s11696-007-0022-7. Go to original source...
  13. Balouiri M, Sadiki М, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: A review. J. Pharm. Anal. 2016;6:71-9. doi:10.1016/j.jpha.2015. 11. 005. Go to original source... Go to PubMed...
  14. Kovalenko S, Antypenko L, Bilyi A, et al. Synthesis and anticancer activity of 2-(alkyl-, alkaryl-, aryl-, hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines. Sci.Pharm. 2013;81:359-91. doi:10.3797/scipharm.1211-08. Go to original source... Go to PubMed...
  15. Sergeieva T, Bilichenko M, Holodnyak S et al. Origin of substituent effect on tautomeric behavior of 1,2,4-triazole derivatives: combined spectroscopic and theoretical study. J. Phys. Chem. A. 2016;120:10116-22. doi:10.1021/acs.jpca.6b08317. Go to original source... Go to PubMed...




Czech and Slovak Pharmacy

Madam, Sir,
please be aware that the website on which you intend to enter, not the general public because it contains technical information about medicines, including advertisements relating to medicinal products. This information and communication professionals are solely under §2 of the Act n.40/1995 Coll. Is active persons authorized to prescribe or supply (hereinafter expert).
Take note that if you are not an expert, you run the risk of danger to their health or the health of other persons, if you the obtained information improperly understood or interpreted, and especially advertising which may be part of this site, or whether you used it for self-diagnosis or medical treatment, whether in relation to each other in person or in relation to others.

I declare:

  1. that I have met the above instruction
  2. I'm an expert within the meaning of the Act n.40/1995 Coll. the regulation of advertising, as amended, and I am aware of the risks that would be a person other than the expert input to these sites exhibited


No

Yes

If your statement is not true, please be aware
that brings the risk of danger to their health or the health of others.