Synthesis and in Vitro Antioxidant Activity Evaluation of 3-Carboxycoumarin Derivatives and QSAR Study of Their DPPH• Radical Scavenging Activity

Molecules

Francisco J. Martínez-Martínez¹  Rodrigo Said Razo-Hernández¹  Ana Lilia Peraza-Campos¹  Manuel Villanueva-García¹  Maria Teresa Sumaya-Martínez¹  Daniel Jaramillo Cano¹ 

[1] ¹Facultad de Ciencias Químicas, Universidad de Colima, kilómetro 9 carretera Colima-Coquimatlán, Col., México, C.P. 28400, Mexico

关键词: coumarins;    QSAR;    DPPH•;    artificial neural networks;   

DOI  :  10.3390/molecules171214882

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.