title: Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and QSAR study of their DPPH• radical scavenging activity.
abstract: The in vitro antioxidant activities of eight 3-carboxycoumarin derivatives were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazil (DPPH•) radical scavenging activity method. 3-Acetyl-6-hydroxy-2H-1-benzopyran-2-one (C1) and ethyl 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate (C2) presented the best radical-scavenging activity. A quantitative structure-activity relationship (QSAR) study was performed and correlated with the experimental DPPH• scavenging data. We used structural, geometrical, topological and quantum-chemical descriptors selected with Genetic Algorithms in order to determine which of these parameters are responsible of the observed DPPH• radical scavenging activity. We constructed a back propagation neural network with the hydrophilic factor (Hy) descriptor to generate an adequate architecture of neurons for the system description. The mathematical model showed a multiple determination coefficient of 0.9196 and a root mean squared error of 0.0851. Our results shows that the presence of hydroxyl groups on the ring structure of 3-carboxy-coumarins are correlated with the observed DPPH• radical scavenging activity effects.
authors.affiliation: Facultad de Ciencias Químicas, Universidad de Colima, kilómetro 9 carretera Colima-Coquimatlán, Col, México CP 28400, Mexico. fjmartin@ucol.mx
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Martínez-Martínez
authors.forename: Rodrigo Said
authors.initials: RS
authors.lastname: Razo-Hernández
authors.forename: Ana Lilia
authors.initials: AL
authors.lastname: Peraza-Campos
authors.forename: Manuel
authors.initials: M
authors.lastname: Villanueva-García
authors.forename: Maria Teresa
authors.initials: MT
authors.lastname: Sumaya-Martínez
authors.forename: Daniel Jaramillo
authors.initials: DJ
authors.lastname: Cano
authors.forename: Zeferino
authors.initials: Z
authors.lastname: Gómez-Sandoval
mesh_terms: D000465:Algorithms; D001578:Benzopyrans / Q000138:chemical synthesis / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry; D019295:Computational Biology; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology*; D008962:Models, Theoretical; D010851:Picrates / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship
chemical_list: C583812:3-acetyl-6-hydroxy-2H-1-benzopyran-2-one; C583813:6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate; D001578:Benzopyrans; D001713:Biphenyl Compounds; D003374:Coumarins; D016166:Free Radical Scavengers; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl