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Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity

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 productio...

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Autores principales: Jung, Jae-Chul, Lee, Yeonju, Son, Jee-Young, Lim, Eunyoung, Jung, Mankil, Oh, Seikwan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268879/
https://www.ncbi.nlm.nih.gov/pubmed/22945025
http://dx.doi.org/10.3390/molecules170910446
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author Jung, Jae-Chul
Lee, Yeonju
Son, Jee-Young
Lim, Eunyoung
Jung, Mankil
Oh, Seikwan
author_facet Jung, Jae-Chul
Lee, Yeonju
Son, Jee-Young
Lim, Eunyoung
Jung, Mankil
Oh, Seikwan
author_sort Jung, Jae-Chul
collection PubMed
description 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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spelling pubmed-62688792018-12-12 Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity Jung, Jae-Chul Lee, Yeonju Son, Jee-Young Lim, Eunyoung Jung, Mankil Oh, Seikwan Molecules Article 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. MDPI 2012-09-03 /pmc/articles/PMC6268879/ /pubmed/22945025 http://dx.doi.org/10.3390/molecules170910446 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Jung, Jae-Chul
Lee, Yeonju
Son, Jee-Young
Lim, Eunyoung
Jung, Mankil
Oh, Seikwan
Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
title Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
title_full Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
title_fullStr Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
title_full_unstemmed Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
title_short Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
title_sort simple synthesis of modafinil derivatives and their anti-inflammatory activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268879/
https://www.ncbi.nlm.nih.gov/pubmed/22945025
http://dx.doi.org/10.3390/molecules170910446
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