title: A quantum chemical and statistical study of flavonoid compounds (flavones) with anti-HIV activity.
abstract: The molecular orbital semi-empirical method AM1 was employed to calculate a set of molecular properties (variables) of 22 flavonoid compounds (flavones) with anti-HIV-1 activity and nine new compounds were proposed for anti-HIV-1 activity prediction. Pattern recognition techniques, principal component analysis (PCA), hierarchical cluster analysis (HCA), stepwise discriminant analysis (SDA) and K-nearest neighbor (KNN), were employed in order to reduce dimensionality and investigate which subset of variables could be more effective for classifying the flavones according to their degree of anti-HIV-1 activity. The PCA, HCA, SDA and KNN studies showed that the variables log P (partition coefficient), molecular volume (VOL) and electron affinity (EA) are responsible for the separation between anti-HIV-1 active and inactive compounds. The prediction study was done with a new set of nine analog compounds by using the PCA, HCA, SDA and KNN methods and only one of them was predicted as active against HIV-1.
authors.affiliation: Departamento de Química e Física Molecular, Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, 13560-970 São Carlos, SP, Brazil.
authors.forename: Jaime
authors.initials: J
authors.lastname: Souza
authors.forename: Regina Helena de Almeida
authors.initials: RH
authors.lastname: Santos
authors.forename: Márcia Miguel Castro
authors.initials: MM
authors.lastname: Ferreira
authors.forename: Fábio Alberto
authors.initials: FA
authors.lastname: Molfetta
authors.forename: Ademir João
authors.initials: AJ
authors.lastname: Camargo
authors.forename: Káthia Maria
authors.initials: KM
authors.lastname: Honório
authors.forename: Albérico Borges Ferreira
authors.initials: AB
authors.lastname: da Silva
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry*; D016000:Cluster Analysis; D005419:Flavonoids / Q000737:chemistry*; D025341:Principal Component Analysis / Q000379:methods*; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D005419:Flavonoids