title: Quantitative structure-activity relationships for 5-substituted 8-hydroxyquinolines as inhibitors of dental plaque.
abstract: Fourteen 8-hydroxyquinolines were tested for antiplaque activity by measuring their minimum inhibitory concentrations [MIC (M)] against Streptococcus mutans No. 6715. Linear regression analysis was conducted with the MIC (M) values and hydrophobic (log P), electronic (beta, pKaOH, pKaN), and steric [molar refractivity (MR), molecular weight (mol wt)] parameters. The best correlation (r2 = 0.90) was obtained with MR, log P, and beta. The smaller the steric contribution of the 5-substituent, the more active the compound. The parent 8-hydroxyquinoline was the most active. The negative contribution toward activity by 5-substituents larger than hydrogen can be overcome by the positive contributions of groups that are lipophilic and electron withdrawing; for example, the 5-chloro derivative is as active as the parent 8-hydroxyquinolines.
mesh_terms: D003773:Dental Plaque / Q000517:prevention & control*; D006912:Hydroxyquinolines / Q000031:analogs & derivatives*; D015125:Oxyquinoline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012044:Regression Analysis; D013295:Streptococcus mutans / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D006912:Hydroxyquinolines; D015125:Oxyquinoline