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Title: Antioxidant, cytotoxicity, and QSAR study of 1-Adamantylthio derivatives of 3-picoline and phenylpyridines
Authors: Worachartcheewan A.
Prachayasittikul S.
Pingaew R.
Nantasenamat C.
Tantimongcolwat T.
Prachayasittikul S.R.
Prachayasittikul V.
Keywords: 1,1 diphenyl 2 picrylhydrazyl
picoline derivative
pyridine derivative
antioxidant activity
biological activity
drug structure
molecular weight
proton nuclear magnetic resonance
quantitative structure activity relation
quantum chemistry
Issue Date: 2012
Abstract: A series of isomeric α-And β-(1-Adamantylthio) pyridines were previously documented to possess interesting antimicrobial and antimalarial activities. In this study, the antioxidant and cytotoxic potentials of 1-Adamantylthio-3-methyl and 2-,3-,4-phenylpyridines (1-10) were investigated. The tested compounds were shown to exhibit interesting superoxide (SOD)-And free radical (DPPH)-scavenging activities as well as cytotoxic activities. Particularly, β-(1-Adamantylthio)-4-phenylpyridine (8) was shown to be the most potent antioxidant and cytotoxic compound. QSAR studies revealed that dipole moment (l) and electrophilic index (xi) were the most important descriptors accounting for the observed SOD activities. Compounds with high l and xi values were observed to display high SOD activity. Inversely, compounds with the lowest atomic polarizability (MATS4p) exhibited the highest DPPH activity. Other quantum chemical descriptors such as atomic masses (GATS4m), xi, and LUMO energy were also well correlated with cytotoxicity. The findings demonstrated that thiopyridine 8 is a potential lead compound that should be further investigated in drug discovery efforts. The QSAR results offer good prospect for the rational design of novel compounds with robust bioactivities. © Springer Science+Business Media, LLC 2011.
ISSN: 10542523
Appears in Collections:SCOPUS 1983-2021

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