Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors

A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy)propanoate followed by hydrolysis and then reacting with different substituted amines. T...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-11, Vol.22 (21), p.6745-6749
Main Authors: Rambabu, D., Mulakayala, Naveen, Ismail, Ravi Kumar, K., Pavan Kumar, G., Mulakayala, Chaitanya, Kumar, Chitta Suresh, Kalle, Arunasree M., Basaveswara Rao, M.V., Oruganti, Srinivas, Pal, Manojit
Format: Article
Language:English
Subjects:
Amides - chemistry
amines
Benzopyrans - chemistry
Biological and medical sciences
chemical structure
Coumarin
Coumarins - chemistry
Coumarins - pharmacology
Crystallography, X-Ray
Cyclooxygenase
Cyclooxygenase Inhibitors - chemical synthesis
Cyclooxygenase Inhibitors - chemistry
Cyclooxygenase Inhibitors - pharmacology
Docking
Enzyme Activation - drug effects
hydrolysis
Indexing in process
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Propane - chemistry
prostaglandin synthase
Protein Binding - drug effects
X-ray
X-ray diffraction
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Summary:A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy)propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular structures of two representative compounds, that is, 3 and 5l were confirmed by single crystal X-ray diffraction study. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. The compound 5i showed balanced selectivity towards COX-2 over COX-1 inhibition and good docking scores when docked into the COX-2 protein.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.08.082