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Title: Antioxidant, cytotoxicity, and QSAR study of 1-Adamantylthio derivatives of 3-picoline and phenylpyridines
Authors: Apilak Worachartcheewan
Supaluk Prachayasittikul
Ratchanok Pingaew
Chanin Nantasenamat
Tanawut Tantimongcolwat
Somsak Ruchirawat Prachayasittikul
Virapong Prachayasittikul
Mahidol University
Srinakharinwirot University
Chulabhorn Research Institute
Keywords: Chemistry;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 1-Nov-2012
Citation: Medicinal Chemistry Research. Vol.21, No.11 (2012), 3514-3522
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: 15548120
Appears in Collections:Scopus 2011-2015

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