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Synthesis, α-glucosidase inhibitory and molecular docking studies of prenylated and geranylated flavones, isoflavones and chalcones
- Source :
- Bioorganic and Medicinal Chemistry Letters, Bioorganic and Medicinal Chemistry Letters, 2015, 25 (20), pp.4567--4571. ⟨10.1016/j.bmcl.2015.08.059⟩, Bioorganic and Medicinal Chemistry Letters, Elsevier, 2015, 25 (20), pp.4567--4571. ⟨10.1016/j.bmcl.2015.08.059⟩
- Publication Year :
- 2015
- Publisher :
- Elsevier BV, 2015.
-
Abstract
- Three series of prenylated and/or geranylated flavonoids were synthesized and evaluated for their α-glucosidase inhibitory activity. The 3',5'-digeranylated chalcone (16) was identified as a new α-glucosidase inhibitor whose activity (IC50=0.90 μM) was 50-fold more than that of acarbose (IC50=51.32 μM). Molecular docking studies revealed the existence of strong hydrophobic interaction and H-bonding between compound 16 and α-glucosidase's active site. The inhibitory mode analysis showed that 16 exhibited a competitive inhibitory mode.
- Subjects :
- Chalcone
Stereochemistry
Clinical Biochemistry
Flavonoid
Pharmaceutical Science
010402 general chemistry
01 natural sciences
Biochemistry
Flavones
Molecular Docking Simulation
Structure-Activity Relationship
chemistry.chemical_compound
Chalcones
Drug Discovery
Humans
[CHIM]Chemical Sciences
Structure–activity relationship
Glycoside Hydrolase Inhibitors
Molecular Biology
IC50
ComputingMilieux_MISCELLANEOUS
chemistry.chemical_classification
Dose-Response Relationship, Drug
Molecular Structure
biology
010405 organic chemistry
Organic Chemistry
Active site
alpha-Glucosidases
Isoflavones
0104 chemical sciences
chemistry
biology.protein
Molecular Medicine
Subjects
Details
- ISSN :
- 0960894X
- Volume :
- 25
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry Letters
- Accession number :
- edsair.doi.dedup.....8b5b7971157d2a0ada470bb33d1264da