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Synthesis and screening of (E)-3-(2-benzylidenehydrazinyl)-5,6-diphenyl-1,2,4-triazine analogs as novel dual inhibitors of α-amylase and α-glucosidase
- Source :
- Bioorganic chemistry. 101
- Publication Year :
- 2020
-
Abstract
- (E)-3-(2-Benzylidenehydrazinyl)-5,6-diphenyl-1,2,4-triazines analogs 1–27 were synthesized by multi-step reaction scheme and subjected to in vitro inhibitory screening against α-amylase and α-glucosidase enzymes. Out of these twenty-seven synthetic analogs, ten compounds 14–17, 19, and 21–25 are structurally new. All compounds exhibited good to moderate inhibitory potential in terms of IC50 values ranging (IC50 = 13.02 ± 0.04–46.90 ± 0.05 µM) and (IC50 = 13.09 ± 0.08–46.44 ± 0.24 µM) in comparison to standard acarbose (IC50 = 12.94 ± 0.27 µM and 10.95 ± 0.08 µM), for α-amylase and α-glucosidase, respectively. Structure-activity relationship indicated that analogs with halogen substitution(s) were found more active as compared to compounds bearing other substituents. Kinetic studies on most active α-amylase and α-glucosidase inhibitors 5, 7, 9, 15, 24, and 27, suggested non-competitive and competitive types of inhibition mechanism for α-amylase and α-glucosidase, respectively. Molecular docking studies predicted the good protein-ligand interaction (PLI) profile with key interactions such as arene-arene, H
- Subjects :
- Molecular model
Stereochemistry
Kinetics
01 natural sciences
Biochemistry
chemistry.chemical_compound
Structure-Activity Relationship
Drug Discovery
medicine
Structure–activity relationship
Humans
Amylase
Molecular Biology
Triazine
Acarbose
chemistry.chemical_classification
biology
Molecular Structure
010405 organic chemistry
Chemistry
Triazines
Organic Chemistry
alpha-Glucosidases
In vitro
0104 chemical sciences
Molecular Docking Simulation
010404 medicinal & biomolecular chemistry
Enzyme
Diabetes Mellitus, Type 2
biology.protein
alpha-Amylases
medicine.drug
Subjects
Details
- ISSN :
- 10902120
- Volume :
- 101
- Database :
- OpenAIRE
- Journal :
- Bioorganic chemistry
- Accession number :
- edsair.doi.dedup.....25233d9d9c7e8f2e38cbf851c07d3561