Skip to content
2000
Volume 15, Issue 1
  • ISSN: 1573-4064
  • E-ISSN: 1875-6638

Abstract

Background: Despite many side effects associated, there are many drugs which are being clinically used for the treatment of type-II diabetes mellitus (DM). In this scenario, there is still need to develop new therapeutic agents with more efficacy and less side effects. By keeping in mind the diverse spectrum of biological potential associated with coumarin and thiazole, a hybrid class based on these two heterocycles was synthesized. Method: Hydrazinyl thiazole substituted coumarins 4-20 were synthesized via two step reaction. First step was the acid catalyzed reaction of 3-formyl/acetyl coumarin derivatives with thiosemicarbazide to form thiosemicarbazone intermediates 1-3, followed by the reaction with different phenacyl bromides to afford products 4-20. All the synthetic analogs 4-20 were characterized by different spectroscopic techniques such as EI-MS, HREI-MS, 1H-NMR and 13C-NMR. Stereochemical assignment of the iminic double bond was carried out by the NOESY experiments. Elemental analysis was found in agreement with the calculated values. Results: Compounds 4-20 were screened for α-amylase inhibitory activity and showed good activity in the range of IC50 = 1.829 ± 0.102-3.37 ± 0.17 μM as compared to standard acarbose (IC50 = 1.819 ± 0.19 μM). Compounds were also investigated for their DPPH and ABTS radical scavenging activities and displayed good radical scavenging potential. In addition to that molecular modelling study was conducted on all compounds to investigate the interaction details of compounds 4- 20 (ligands) with active site (receptor) of enzyme. Conclusion: The newly identified hybrid class may serve as potential lead candidates for the management of diabetes mellitus.

Loading

Article metrics loading...

/content/journals/mc/10.2174/1573406414666180903162243
2019-02-01
2025-06-01
Loading full text...

Full text loading...

/content/journals/mc/10.2174/1573406414666180903162243
Loading

  • Article Type:
    Research Article
Keyword(s): ABTS; Coumarin; DPPH; hydrazinyl thiazole; in silico; in vitro; α-amylase activity
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test