Synthesis, anti-hyperglycaemic activity, and in-silico studies of class="a-plus-plus">N-substituted 5-(furan-2-ylmethylene)thiazolidine-2,4-dione derivatives

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• 作者：Manoj Kumar Mahapatra ; Rajnish Saini ; Manoj Kumar
• 关键词：Diabetes ; N ; substituted thiazolidine ; 2 ; 4 ; dione ; Anti ; hyperglycaemic activity ; Docking
• 刊名：Research on Chemical Intermediates
• 出版年：2016
• 出版时间：December 2016
• 年：2016
• 卷：42
• 期：12
• 页码：8239-8251
• 全文大小：667 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675
• 卷排序：42

文摘

Thiazolidinedione derivatives have been used as anti-hyperglycemic agents in diabetic patients since last decade. In the present study, a series of N-substituted-5-(furan-2-ylmethylene)thiazolidine-2,4-dione derivatives were synthesized and characterized by 1H-NMR, 13C-NMR and mass spectra. The introduction of the alkyl/haloalkyl moiety onto the amidic nitrogen of the thiazolidine-2,4-dione ring was intended to enhance the anti-hyperglycaemic activity, which was further tested in vivo by using alloxan-induced diabetic laca mice. Molecular docking simulation studies further helped in understanding the nature of the interactions and the binding mode of ligands inside the active site of the protein tyrosine phosphatase 1B enzyme, which negatively regulates the insulin signaling pathway. The compounds were screened for in-vivo anti-hyperglycaemic activity in which compounds 9 and 10 have exhibited significant decreases in blood glucose level comparable to that of pioglitazone.