title: Molecular electrostatic potentials in aromatic substituted 4-hydroxyquino-2-lones: glycine/NMDA receptor antagonists.
abstract: Hydroxyquinolone derivatives have proven to be useful for inhibition at the glycine binding site of N-methyl-D-aspartate (NMDA) receptor. In this work the electronic structure, molecular electrostatic potential (MESP) and vibrational characteristics of a set of C(3) substituted 4-hydroxyquino-2-lone (HQ) derivatives, which act as Glycine/NMDA receptor antagonists, have been investigated using the density functional calculations. In the optimized structures a substituent at the C(3) site of HQ tends to adopt a helical structure. MESP investigations reveal that the ligands showing better inhibition activity should possess electron-rich regions extending over the substituent and carbonyl group of HQ. A correlation of inhibitory activity to the molecular electrostatic potential topography at the carbonyl oxygen as well as to the molecular electron density topography turns out to be a significant output of the investigation.
authors.affiliation: Department of Chemistry, University of Pune, Pune, 411 007, India.
authors.forename: Kaustubh A
authors.initials: KA
authors.lastname: Joshi
authors.forename: Dinannath D
authors.initials: DD
authors.lastname: Patil
authors.forename: Shridhar P
authors.initials: SP
authors.lastname: Gejji
mesh_terms: D000818:Animals; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D015363:Quinolones / Q000737:chemistry*; D016194:Receptors, N-Methyl-D-Aspartate / Q000037:antagonists & inhibitors*; D055672:Static Electricity
chemical_list: D015363:Quinolones; D016194:Receptors, N-Methyl-D-Aspartate