title: Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors.
abstract: 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.
authors.affiliation: Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500 046, India.
authors.forename: D
authors.initials: D
authors.lastname: Rambabu
authors.forename: Naveen
authors.initials: N
authors.lastname: Mulakayala
authors.lastname: Ismail
authors.forename: K Ravi
authors.initials: KR
authors.lastname: Kumar
authors.forename: G Pavan
authors.initials: GP
authors.lastname: Kumar
authors.forename: Chaitanya
authors.initials: C
authors.lastname: Mulakayala
authors.forename: Chitta Suresh
authors.initials: CS
authors.lastname: Kumar
authors.forename: Arunasree M
authors.initials: AM
authors.lastname: Kalle
authors.forename: M V Basaveswara
authors.initials: MV
authors.lastname: Rao
authors.forename: Srinivas
authors.initials: S
authors.lastname: Oruganti
authors.forename: Manojit
authors.initials: M
authors.lastname: Pal
mesh_terms: D000577:Amides / Q000737:chemistry*; D001578:Benzopyrans / Q000737:chemistry*; D003374:Coumarins / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004789:Enzyme Activation / Q000187:drug effects; D015394:Molecular Structure; D011407:Propane / Q000737:chemistry*; D011485:Protein Binding / Q000187:drug effects
chemical_list: D000577:Amides; D001578:Benzopyrans; D003374:Coumarins; D016861:Cyclooxygenase Inhibitors; C030123:coumarin; D011407:Propane