A generalstrategy for the synthesis of 3,4-dioxygenated quinolin-2-one naturalproducts is reported. The key step is a regioselective insertion of arynes into unsymmetric imides. When performed in continuousflow, the reaction proceeds within minutes, while lower yields and longer reaction times are observed in batch. The resulting N-acylated 2-aminobenzophenones were transformed to (±)-peniprequinolone
Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties
作者:Nigel Ribeiro、Helena Tabaka、Jean Peluso、Ludivine Fetzer、Can Nebigil、Serge Dumont、Christian D. Muller、Laurent Désaubry
DOI:10.1016/j.bmcl.2007.08.036
日期:2007.10
We synthesized 3-O-methylviridicatin 1 and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-alpha secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents. (c) 2007 Elsevier Ltd. All rights reserved.