Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity

doi:10.3390/molecules170910446

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Molecules 2012, 17(9), 10446-10458; doi:10.3390/molecules170910446

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Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity

Jae-Chul Jung¹, Yeonju Lee¹, Jee-Young Son², Eunyoung Lim², Mankil Jung² and Seikwan Oh^1,*

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.

Received: 2 July 2012; in revised form: 10 August 2012 / Accepted: 14 August 2012 / Published: 3 September 2012

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Abstract: 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.

Keywords: modafinil; anti-inflammation; nitric oxide; S-alkylation; coupling reaction

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Cite This Article

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.

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.

Chicago/Turabian Style

Jung, Jae-Chul; Lee, Yeonju; Son, Jee-Young; Lim, Eunyoung; Jung, Mankil; Oh, Seikwan. 2012. "Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity." Molecules 17, no. 9: 10446-10458.

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