SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY EVALUATION OF RHODANINE DERIVATIVES WITH 2-(2,6-DICHLOROPHENYLAMINO)-PHENYLACETAMIDE FRAGMENT IN MOLECULES

Authors

  • Yu. L. Shepeta M. Pyrohov Vinnytsia National Medical University
  • M. I. Lelyukh Danylo Halytsky Lviv National Medical University
  • B. S. Zimenkovsky Danylo Halytsky Lviv National Medical University
  • I. O. Nektegayev Danylo Halytsky Lviv National Medical University
  • R. B. Lesyk Danylo Halytsky Lviv National Medical University

DOI:

https://doi.org/10.11603/2312-0967.2018.1.8601

Keywords:

synthesis, 2-thioxo-4-thiazolidinone, diclofenac, heterocyclization reaction, Knoevenagel condensation, spectral data, anti-inflammatory activity.

Abstract

The aim of work. Synthesize the new 5-ylidenerhodanine derivatives with diclofenac fragment in position 3 based on the heterocyclization reaction and Knoevenagel condensation for screening their anti-inflammatory activity.

Materials and Methods. Organic synthesis, NMR spectroscopy, elemental analysis, pharmacological screening, SAR-analysis.

Results and Discussion. The interaction of 2-(2,6-dichlorophenylamino)phenylacetic acid hydrazide and thiocarbonyl-bis-thioglycolic acid in ethanol medium resulted in rhodanine derivative with fragment of anti-inflammatory drug «Diclofenac» in position 3. Considering the presence of an active methylene group in position 5 the further chemical modification of synthesized rhodanine was performed via Knoevenagel condensation with various aromatic aldehydes, isatin or cinnamic aldehyde derivatives have yielded a series of 5-arylidene- and 5-isatin(3-phenylpropene)ylidene derivatives for pharmacological screening on antiexudative action. The structure of obtained compounds was confirmed by NMR spectroscopy and elemental analysis.

Conclusions. The results of anti-inflammatory activity investigation of synthesized compounds allowed us to identify three highly active derivatives which was appropriate to the reference nonsteroidal inflammatory drug «Diclofenac Sodium» by indicator of inhibition of inflammatory reaction (42,4-45,3%).

Author Biographies

Yu. L. Shepeta, M. Pyrohov Vinnytsia National Medical University

Assistant Professor, Department of Pharmaceutical Chemistry, M. Pirogov Vinnytsya National Medical University

M. I. Lelyukh, Danylo Halytsky Lviv National Medical University

Candidate of Pharmaceutical Sciences, PhD (PharmSc), Assistant Professor, Department of Pharmaceutical Chemistry, Faculty of Postgraduate Education, Danylo Halytsky Lviv National Medical University

B. S. Zimenkovsky, Danylo Halytsky Lviv National Medical University

Doctor of Pharmaceutical Sciences (DSc),  Academician of the National Academy of Medical Sciences of Ukraine, Rector of  Danylo Halytsky Lviv National Medical University, Professor of the Department of Pharmaceutical, Organic and Bioorganic Chemistry

I. O. Nektegayev, Danylo Halytsky Lviv National Medical University

Senior Laboratory Technician, Department of Pharmacology, Danylo Halytsky Lviv National Medical University

R. B. Lesyk, Danylo Halytsky Lviv National Medical University

Doctor of Pharmaceutical Sciences (DSc), Professor, Head of the Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University

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Published

2018-03-24

How to Cite

Shepeta, Y. L., Lelyukh, M. I., Zimenkovsky, B. S., Nektegayev, I. O., & Lesyk, R. B. (2018). SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY EVALUATION OF RHODANINE DERIVATIVES WITH 2-(2,6-DICHLOROPHENYLAMINO)-PHENYLACETAMIDE FRAGMENT IN MOLECULES. Pharmaceutical Review Farmacevtičnij časopis, (1), 6–15. https://doi.org/10.11603/2312-0967.2018.1.8601

Issue

No. 1 (2018)

Section

Synthesis of biologically active compounds

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