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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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