Synthesis and PGE(2) production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives

Jong Taik Moon; Ji Young Jeon; Hang Ah Park; Young-Soo Noh; Kyung-Tae Lee; Jungahn Kim; Dong Joon Choo; Jae Yeol Lee

doi:10.1016/j.bmcl.2009.11.067

Synthesis and PGE(2) production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives

Bioorg Med Chem Lett. 2010 Jan 15;20(2):734-7. doi: 10.1016/j.bmcl.2009.11.067. Epub 2009 Dec 11.

Authors

Jong Taik Moon¹, Ji Young Jeon, Hang Ah Park, Young-Soo Noh, Kyung-Tae Lee, Jungahn Kim, Dong Joon Choo, Jae Yeol Lee

Affiliation

¹ Research Institute for Basic Sciences and Department of Chemistry, College of Sciences, Kyung Hee University, Seoul 130-701, Republic of Korea.

PMID: 20004572
DOI: 10.1016/j.bmcl.2009.11.067

Abstract

3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC(50)=0.61microM) of PGE(2) production.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / pharmacology
Cell Line, Tumor
Dinoprostone / metabolism*
Furans / chemical synthesis
Furans / chemistry*
Furans / pharmacology
Maleimides / chemical synthesis*
Maleimides / chemistry
Maleimides / pharmacology
Mice
Structure-Activity Relationship
Sulfonamides / chemical synthesis*
Sulfonamides / chemistry
Sulfonamides / pharmacology

Substances

1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione
Anti-Inflammatory Agents, Non-Steroidal
Furans
Maleimides
Sulfonamides
Dinoprostone
furan