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. 2024 Oct 17;25(20):11130.
doi: 10.3390/ijms252011130.

Biological Activity Evaluation of Phenolic Isatin-3-Hydrazones Containing a Quaternary Ammonium Center of Various Structures

Margarita Neganova  1   2   3 , Yulia Aleksandrova  1   2   3 , Alexandra Voloshina  1 , Anna Lyubina  1 , Nurbol Appazov  3   4 , Sholpan Yespenbetova  3 , Zulfiia Valiullina  5 , Aleksandr Samorodov  5 , Sergey Bukharov  6 , Elmira Gibadullina  1   3 , Anipa Tapalova  3 , Andrei Bogdanov  1
Affiliations

Biological Activity Evaluation of Phenolic Isatin-3-Hydrazones Containing a Quaternary Ammonium Center of Various Structures

Margarita Neganova et al. Int J Mol Sci. .

Abstract

A series of new isatin-3-hydrazones bearing different ammonium fragments was synthesized by a simple and easy work-up reaction of Girard's reagents analogs with 1-(3,5-di-tert-butyl-4-hydroxybenzyl)isatin. All derivatives have been shown to have antioxidant properties. In terms of bactericidal activity against gram-positive bacteria, including methicillin-resistant strains of Staphylococcus aureus, the best compounds are 3a, 3e, and 3m, bearing octyl, acetal, and brucine ammonium centers, respectively. In addition, brucine and quinine derivatives 3l, and 3j exhibit platelet antiaggregation activity at the level of acetylsalicylic acid, and this series of isatin derivatives does not adversely affect the hemostasis system as a whole. Thus, all the obtained results can lay the groundwork for future pharmaceutical developments for the creation of effective antibacterial drugs with reduced systemic toxicity due to the presence of antioxidant properties.

Keywords: antioxidants; cytotoxicity; hemostasis; hydrazones; isatin; quaternary ammonium compounds.

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Conflict of interest statement

Author Nurbol Appazov was employed by the company “CNEC” LLP. The remaining authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

Figure 1
Figure 1
Representatives of isatin acylhydrazones with different bioactivities.
Figure 2
Figure 2
Previously published phenolic isatin hydrazones with antimicrobial activity [25,26,27].
Scheme 1
Scheme 1
Two-step synthesis of ammonium acetohydrazides.
Scheme 2
Scheme 2
Synthesis of isatin hydrazones containing an ammonium center of various structures.
Scheme 3
Scheme 3
New isatin-3-acylhydrazones based on brucine alkaloid.
Figure 3
Figure 3
Hemotoxic and cytotoxic activity of 3a–3n, expressed in terms of HC50 и IC50; * Values indicate p < 0.01.
Figure 4
Figure 4
Summary of biological activity data of phenolic isatin-3-hydrazones.
See this image and copyright information in PMC

References

    1. Cheke R.S., Firke S.D., Patil R.R., Bari S.B. ISATIN: New Hope Against Convulsion. Cent. Nerv. Syst. Agents Med. Chem. 2018;18:76–101. doi: 10.2174/1871524917666171113124112. - DOI - PubMed
    1. Saini T., Kumar S., Narasimhan B. Central Nervous System Activities of Indole Derivatives: An Overview. Cent. Nerv. Syst. Agents Med. Chem. 2015;16:19–28. doi: 10.2174/1871524915666150608103224. - DOI - PubMed
    1. Medvedev A., Igosheva N., Crumeyrolle-Arias M., Glover V. Isatin: Role in stress and anxiety. Stress. 2005;8:175–183. doi: 10.1080/10253890500342321. - DOI - PubMed
    1. Bharathi Dileepan A.G., Daniel Prakash T., Ganesh Kumar A., Shameela Rajam P., Violet Dhayabaran V., Rajaram R. Isatin based macrocyclic Schiff base ligands as novel candidates for antimicrobial and antioxidant drug design: In vitro DNA binding and biological studies. J. Photochem. Photobiol. B. 2018;183:191–200. doi: 10.1016/j.jphotobiol.2018.04.029. - DOI - PubMed
    1. Raj R., Gut J., Rosenthal P.J., Kumar V. 1H-1,2,3-Triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates: Synthesis and antimalarial evaluation. Bioorg. Med. Chem. Lett. 2014;24:756–759. doi: 10.1016/j.bmcl.2013.12.109. - DOI - PubMed

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