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α-glucosidase inhibitors, including acarbose (Precose), miglitol (Glyset), and voglibose (Voglib) (primarily available in Asia), are drugs that control blood sugar levels by delaying the digestion of starch and disaccharides. They achieve this by inhibiting α-glucosidase enzymes in the intestine, which slow the absorption of carbohydrates in the intestine, which in turn leads to a prolonged release of the glucoregulatory hormone GLP-1 from intestinal L-cells.
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Dipeptidyl peptidase 4 (DPP-4) is a serine protease widely distributed in the body. It's involved in the inactivation of GLP-1 and GIP hormones, which are crucial for insulin regulation. DPP-4 inhibitors, such as sitagliptin (Januvia), saxagliptin (Onglyza), linagliptin (Tradjenta), alogliptin (Nesina), and vildagliptin (Galvus), help increase the proportion of active GLP-1, enhancing insulin secretion. These inhibitors work by competitively binding to DPP-4. This binding causes a...
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Sulfonylureas are oral hypoglycemic agents utilized in treating type 2 diabetes. They are characterized by their unique sulfonylurea chemical structure. The family of sulfonylureas is divided into generations. First-generation sulfonylureas, including tolbutamide (Orinase), chlorpropamide (Diabinese), and tolazamide (Tolinase), trigger insulin release from pancreatic β cells and enhance peripheral tissues' insulin sensitivity. The second-generation members, such as glipizide...
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Design, Synthesis and Alpha-glucosidase Inhibitory Effect of Pyrazole-1,2,3-Triazole Hybrids.

Suprapaneni Sirisha1, Nagaraju Kerru1,2, Ramakrishna Rao Bhonsle1

  • 1Department of Chemistry, GITAM School of Sciences, GITAM University, Bengaluru, India.

Chemistry & Biodiversity
|May 27, 2025
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Summary

Novel pyrazole-1,2,3-triazole hybrids show potent glucosidase inhibition, with specific compounds outperforming acarbose. These findings offer potential for developing new diabetes mellitus treatments.

Keywords:
1,2,3‐triazoleantidiabeticmolecular hybridizationpyrazoleα‐glucosidase

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Pharmacology

Background:

  • Diabetes mellitus is a global health concern requiring effective management strategies.
  • Glucosidase enzymes play a crucial role in carbohydrate metabolism and are key targets for diabetes therapy.
  • Pyrazole and 1,2,3-triazole scaffolds are recognized for their diverse biological activities.

Purpose of the Study:

  • To synthesize and characterize novel pyrazole-1,2,3-triazole hybrids.
  • To evaluate the potential of these hybrids as α-glucosidase inhibitors.
  • To explore their structure-activity relationships for diabetes mellitus therapeutic development.

Main Methods:

  • Copper-catalyzed azide-alkyne cycloaddition (CuAAC) for hybrid synthesis.
  • In vitro α-glucosidase inhibition assays to determine IC50 values.
  • Molecular docking studies against human lysosomal acid-α-glucosidase.
  • Density Functional Theory (DFT) for electronic property prediction.

Main Results:

  • Successful synthesis of novel pyrazole-1,2,3-triazole hybrids.
  • Compounds bearing 4-nitro and 4-chloro groups exhibited significant α-glucosidase inhibition (IC50 = 3.35 µM and 6.58 µM, respectively), comparable to acarbose (IC50 = 3.86 µM).
  • Molecular docking revealed favorable binding interactions within the enzyme's active site, supported by DFT analysis.

Conclusions:

  • The synthesized pyrazole-1,2,3-triazole hybrids demonstrate promising α-glucosidase inhibitory activity.
  • Electron-withdrawing groups at the para position positively influence enzyme inhibition.
  • These compounds serve as valuable structural models for the development of novel anti-diabetic agents.