Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules

Authors

  • Yu. L. Shepeta Vinnytsia National Pirogov Memorial Medical University, Ukraine,
  • O. M. Roman Danylo Halytsky Lviv National Medical University, Ukraine,
  • I. O. Nektiehaiev Danylo Halytsky Lviv National Medical University, Ukraine,
  • R. B. Lesyk Danylo Halytsky Lviv National Medical University, Ukraine,

DOI:

https://doi.org/10.14739/2409-2932.2020.2.207024

Keywords:

synthesis, 4H-1, 2, 4-triazole, rhodanine, diclofenac, anti-inflammatory activity, anticancer activity

Abstract

Molecular design of “drug-like” molecules based on the combination of a fragment of non-steroidal anti-inflammatory drug diclofenac with a pharmacologically attractive 1,2,4-triazole and 4-thiazolidinone “structural matrices” in one molecule is an effective approach in modern medical chemistry.

Aim. Synthesis of new rhodanine-triazole hybrid molecules (conjugates) with 2- (2,6-dichlorophenylamino) benzyl moiety and evaluation of their biological activity.

Materials and methods. The method of rhodanine-triazoles synthesis was elaborated. The structures of the synthesized compounds were confirmed by elemental analysis, NMR spectroscopy, and LCMS. The anti-exudative activity of the compounds was investigated in a rat carrageenan edema model, and the antitumor effect was studied in vitro at a concentration of 10-5 M on 60 cancer cell lines (DTP NCI Program).

Results. Novel 2-{5-[2-(2,6-dichlorophenylamino)-benzyl]-4H-1,2,4-triazol-3-ylsulfanyl}-N-(4-oxo-2-thioxothiazolidin-3-yl)-acetamides and their 5-arylidene derivatives were synthesized/ Among these derivatives hit compounds with anti-inflammatory and anticancer activity against cell lines of melanoma, leukemia, non-small cell lung cancer, colon cancer, CNS cancer, ovarian cancer, renal cancer, and breast cancer were identified.

Conclusion. The molecular design of rhodanine-triazole hybrid molecules based on diclofenac is an effective approach to the search for novel anti-inflammatory and antitumor agents.

References

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How to Cite

1.
Shepeta YL, Roman OM, Nektiehaiev IO, Lesyk RB. Synthesis and biological activity of new rhodanine-triazole conjugates with 2-(2,6-dichlorophenylamino)benzyl moiety in the molecules. Current issues in pharmacy and medicine: science and practice [Internet]. 2020Jul.3 [cited 2024Apr.14];13(2). Available from: http://pharmed.zsmu.edu.ua/article/view/207024

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Section

Original research