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Molecules 2012, 17(12), 14882-14898; doi:10.3390/molecules171214882
Article

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

1,* , 1, 1, 2
, 3
, 1
 and 1,*
Received: 21 September 2012; in revised form: 3 December 2012 / Accepted: 5 December 2012 / Published: 13 December 2012
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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.
Keywords: coumarins; QSAR; DPPH•; artificial neural networks coumarins; QSAR; DPPH•; artificial neural networks
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Martínez-Martínez, F.J.; Razo-Hernández, R.S.; Peraza-Campos, A.L.; Villanueva-García, M.; Sumaya-Martínez, M.T.; Cano, D.J.; Gómez-Sandoval, Z. Synthesis and in Vitro Antioxidant Activity Evaluation of 3-Carboxycoumarin Derivatives and QSAR Study of Their DPPH• Radical Scavenging Activity. Molecules 2012, 17, 14882-14898.

AMA Style

Martínez-Martínez FJ, Razo-Hernández RS, Peraza-Campos AL, Villanueva-García M, Sumaya-Martínez MT, Cano DJ, Gómez-Sandoval Z. Synthesis and in Vitro Antioxidant Activity Evaluation of 3-Carboxycoumarin Derivatives and QSAR Study of Their DPPH• Radical Scavenging Activity. Molecules. 2012; 17(12):14882-14898.

Chicago/Turabian Style

Martínez-Martínez, Francisco J.; Razo-Hernández, Rodrigo S.; Peraza-Campos, Ana L.; Villanueva-García, Manuel; Sumaya-Martínez, Maria T.; Cano, Daniel J.; Gómez-Sandoval, Zeferino. 2012. "Synthesis and in Vitro Antioxidant Activity Evaluation of 3-Carboxycoumarin Derivatives and QSAR Study of Their DPPH• Radical Scavenging Activity." Molecules 17, no. 12: 14882-14898.


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