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

Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity

1, 1, 2, 2, 2 and 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 / Revised: 10 August 2012 / Accepted: 14 August 2012 / Published: 3 September 2012
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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 11ad) resulted in lower anti-inflammatory activity compared with cyclic or aromatic moieties (compounds 11ek). However, for the sulfoxide analogues, introduction of aliphatic moieties (compounds 12ad) showed higher anti-inflammatory activity than cyclic or aromatic fragments (compounds 12ek) in BV-2 microglia cells.
Keywords: modafinil; anti-inflammation; nitric oxide; S-alkylation; coupling reaction modafinil; anti-inflammation; nitric oxide; S-alkylation; coupling reaction
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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