Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
1
Department of Neuroscience and Tissue Injury Defense Research Center, School of Medicine, Ewha Womans University, Seoul 158-710, Korea
2
Department of Chemistry, Yonsei University, Seoul 120-749, Korea
*
Author to whom correspondence should be addressed.
Molecules 2012, 17(9), 10446-10458; https://doi.org/10.3390/molecules170910446
Received: 2 July 2012
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Revised: 10 August 2012
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Accepted: 14 August 2012
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Published: 3 September 2012
Simple synthesis of modafinil derivatives and their biological activity are described. The key synthetic strategies involve substitution and coupling reactions. We determined the anti-inflammatory effects of modafinil derivatives in cultured BV2 cells by measuring the inhibition of nitrite production and expression of iNOS and COX-2 after LPS stimulation. It was found that for sulfide analogues introduction of aliphatic groups on the amide part (compounds 11a–d) resulted in lower anti-inflammatory activity compared with cyclic or aromatic moieties (compounds 11e–k). However, for the sulfoxide analogues, introduction of aliphatic moieties (compounds 12a–d) showed higher anti-inflammatory activity than cyclic or aromatic fragments (compounds 12e–k) in BV-2 microglia cells.
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Keywords:
modafinil; anti-inflammation; nitric oxide; S-alkylation; coupling reaction
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MDPI and ACS Style
Jung, J.-C.; Lee, Y.; Son, J.-Y.; Lim, E.; Jung, M.; Oh, S. Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity. Molecules 2012, 17, 10446-10458. https://doi.org/10.3390/molecules170910446
AMA Style
Jung J-C, Lee Y, Son J-Y, Lim E, Jung M, Oh S. Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity. Molecules. 2012; 17(9):10446-10458. https://doi.org/10.3390/molecules170910446
Chicago/Turabian StyleJung, Jae-Chul, Yeonju Lee, Jee-Young Son, Eunyoung Lim, Mankil Jung, and Seikwan Oh. 2012. "Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity" Molecules 17, no. 9: 10446-10458. https://doi.org/10.3390/molecules170910446
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