QSAR study of the DPPH· radical scavenging activity of coumarin derivatives and xanthine oxidase inhibition by molecular docking

Razo‐Hernández, Rodrigo Said; Pineda‐Urbina, Kayim; Velazco‐Medel, Marlene A.; Villanueva-García, Manuel; Sumaya-Martínez, M. T.; Martínez‐Martínez, Francisco J.; Gómez‐Sandoval, Zeferino

doi:10.2478/s11532-014-0555-x

Cited by 15 publications

(16 citation statements)

References 53 publications

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“…This finding is in accordance with our results since coumarins without hydroxyl groups were ineffective or they exhibited very low antioxidant activity. Our results are also in agreement with the works of Pedersen et al, 2007, Barzegar et al, 2011and Razo-Hernandez et al, 2014 who found that the most active scavengers of DPPH and galvinoxyl radicals were 6,7-and 7,8-dihydroxy-4-methyl coumarins. Also, Kaneko et al, 2001 found that esculetin bearing a 6,7-dihydroxyl moiety showed a protective effect on linoleic acid hydroperoxide-induced toxicity, whereas 4-and 7-hydroxycomarins were ineffective.…”

Section: Discussionsupporting

confidence: 93%

Antioxidant activity of some coumarins / Antioxidačná activita niektorých kumarínov

Šeršeň¹,

Lácová

2015

Acta Facultatis Pharmaceuticae Universitatis Comenianae

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Nineteen derivatives of coumarin were tested on the scavenging of 2,2-diphenyl-1-picrylhydrazyl, hydroxyl and superoxide anion radicals. It was found that antioxidant activity exhibits only such coumarins that contain hydroxyl groups. The derivatives without hydroxyl group showed very low antioxidant effectiveness or they were ineffective. On the other hand, the greatest antioxidant effectiveness was exhibited by coumarin derivatives that contained hydroxyl groups in 6 or 8 position, whereas the effectiveness of derivatives with one hydroxyl group in 4, 5 or 7 position was very low. Based on scavenging of the above-mentioned radicals, it was found that the most effective scavengers were 7,8-dihydroxy-4-methylcoumarin (i.e. compound that contains two hydroxyl groups in 7 and 8 positions), (7,8-dihydroxy-2-oxo-2H-chromen-4-yl)acetic acid (this compound contains in addition to two hydroxyl groups in 7 and 8 positions also one hydroxyl group in the acidic residue), esculetin (6,7-dihydroxycoumarin) and 6,7-dihydroxy-4-methylcoumarin.

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Section: Discussionsupporting

confidence: 93%

Antioxidant activity of some coumarins / Antioxidačná activita niektorých kumarínov

Šeršeň¹,

Lácová

2015

Acta Facultatis Pharmaceuticae Universitatis Comenianae

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“…S1 and S2, see supporting information). Rather than analyzing the overall biding energies, we followed the method reported previously [38], and searched for interactions with residues that are considered key to selectively binding to each isoform.…”

Section: Molecular Docking Methodologymentioning

confidence: 99%

In silico receptor-based drug design of X,Y-benzenesulfonamide derivatives as selective COX-2 inhibitors

Pérez

Sarabia

Villanueva-García

et al. 2016

Comptes Rendus. Chimie

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a b s t r a c tCOX-2 is a widely studied biological target, since its activity is directly related to the inflammation response. The design of COX-2 selective inhibitors is an ongoing topic in drug design. We performed a quantitative structureeactivity relationship and docking studies over a series of benzenesulfonamide derivatives on their inhibition towards COX-1 and COX-2, in order to rationalize their selectivity towards COX-2. Constitutional, topological and molecular property descriptors for the QSAR models and molecular docking calculations were employed. The mathematical model highlighted that lipophilic character and size are the most important features for COX-2 inhibition by benzenesulfonamides. A second QSAR model revealed that the dipole moment, the number of hydrogen bond donors and lipophilicity descriptors of benzenesulfonamides are crucial for their binding to COX-1. Moreover, artificial neural networks were employed to improve the prediction power of the COX-1 inhibition QSAR model. In this sense, we proposed new selective potential inhibitors by introducing different halogens into the benzenesulfonamide scaffold, improving their interactions with key residues of COX-2.

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“…All the GABA B receptor residues that interact with Baclofen in the crystal structure 4MS4, within 3 Å, were considered as key residues. This approach is derived from other reports from the literature where the use of interaction energies of key residues helps to explain the biological activity of some compounds (Pérez, et al., ; Pérez, Días‐Reval et al., Pérez, Sarabia et al., ; Razo‐Hernández et al., ).…”

Section: Computational Detailsmentioning

confidence: 99%

In silico structure‐based design of GABA_B receptor agonists using a combination of docking and QSAR

et al. 2019

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The study of γ‐aminobutyric acid B receptor (GABAB) activation is of great interest for several brain disorders. The search of new GABAB receptor agonists has been carried out by many research groups. As a result, Baclofen has become the prototypical GABAB receptor agonist. However, several attempts have been made to modify its structure to generate derivatives with improved activity. In this work, we carried out a theoretical and computational study for a wide range of GABAB receptor agonists reported in the literature. Molecular docking and QSAR techniques were combined by using the interaction energies of the agonists with the key residues of GABAB receptor, as molecular descriptors for the QSAR construction. The resulting mathematical model suggests that the activity of GABAB receptor agonists is influenced by three factors: their shape and molecular size (PW5 and PJI2), their constitutional features (ELUMO and T(N…O)) and the energy interaction with GABAB receptor (ETRP278). This model was validated by the QUIK, REDUNDANCY and OVERFITTING rules, and its predicted ability was tasted by the QLOO, QASYM, R02 and rm2 rules. Finally, six new compounds are proposed (35–40) with high potential to be used as GABAB receptor agonists.

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QSAR study of the DPPH· radical scavenging activity of coumarin derivatives and xanthine oxidase inhibition by molecular docking

Cited by 15 publications

References 53 publications

Antioxidant activity of some coumarins / Antioxidačná activita niektorých kumarínov

Antioxidant activity of some coumarins / Antioxidačná activita niektorých kumarínov

In silico receptor-based drug design of X,Y-benzenesulfonamide derivatives as selective COX-2 inhibitors

In silico structure‐based design of GABA_B receptor agonists using a combination of docking and QSAR

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QSAR study of the DPPH· radical scavenging activity of coumarin derivatives and xanthine oxidase inhibition by molecular docking

Cited by 15 publications

References 53 publications

Antioxidant activity of some coumarins / Antioxidačná activita niektorých kumarínov

Antioxidant activity of some coumarins / Antioxidačná activita niektorých kumarínov

In silico receptor-based drug design of X,Y-benzenesulfonamide derivatives as selective COX-2 inhibitors

In silico structure‐based design of GABAB receptor agonists using a combination of docking and QSAR

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In silico structure‐based design of GABA_B receptor agonists using a combination of docking and QSAR