The synthesis, hypoglycemic activity and acute toxicity of new imidazole-thiazolidines hybrid structures

Authors

  • V. O. Chornous Bukovinian State Medical University, Ukraine
  • O. Ya. Melnyk SHHE «Ivano-Frankivsk National Medical University», Ukraine
  • O. M. Hliebov SHHE «Ivano-Frankivsk National Medical University», Ukraine
  • M. V. Tykhonenko SHHE «Ivano-Frankivsk National Medical University», Ukraine
  • L. M. Sheremeta SHHE «Ivano-Frankivsk National Medical University», Ukraine
  • O. K. Yarosh Institute of Pharmacology and Toxicology of the AMS of Ukraine, Ukraine
  • O. M. Denysenko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • R. V. Rodik Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.872

Keywords:

4-chloro-5-formylimidazoles, 1, 3-thiazolidine-4-one, imidazole-thiazolidine structure, synthesis, hypo- glycemic activity, acute toxicity

Abstract

The article presents a brief description of diabetes type 2 as a disease related with carbohydrate metabolism disorder mainly caused by insulin resistance and relative insulin defi ciency. It has been noted that pathologies may appear under the action of drugs of the glitazone group; it is a major cause for systematic search for new bioactive and safe compounds with the hypoglycemic action. Considering the wide range of the biological activity of imidazole derivatives and 1,3-thiazolidine the synthesis of new hybrid structures – 5-[(1-aryl-4-chloro-1H-imidazole-5-yl)methylene]-1,3-thiazolidine-2,4-diones and their exohydrated analogues – 5-[(1-aryl-4-chloro-1H-imidazole-5-yl)methyl]-1,3-thiazolidine-2,4-diones has been carried out. A preparative suitable scheme for their obtaining has been proposed, it is based on condensation of available 1-aryl-4-chloro-5-formylimidazoles with1,3-thiazolidine-4-one and further hydrogenation of the exocyclic ylidene bond formed. The results of biomedical studies of the compounds obtained in the doses of 100, 10 and 1 mg/kg have shown that they have a strong hypoglycemic activity, which exceeds the effect of test drug pioglitazone by 55%. The acute toxicity (LD50) of 5-{[1-(4-tolyl)-4chloro-1H-imidazole-5-yl]methylene}-1,3-thiazolidine-2,4-dione is 1292.92 mg/k when injected intraperitoneally.

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Published

2016-03-04

How to Cite

(1)
Chornous, V. O.; Melnyk, O. Y.; Hliebov, O. M.; Tykhonenko, M. V.; Sheremeta, L. M.; Yarosh, O. K.; Denysenko, O. M.; Rodik, R. V.; Vovk, M. V. The Synthesis, Hypoglycemic Activity and Acute Toxicity of New Imidazole-Thiazolidines Hybrid Structures. J. Org. Pharm. Chem. 2016, 14, 46-52.

Issue

Vol. 14 No. 1(53) (2016)

Section

Original Researches

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