A modular and efficient synthesis of the biologically significant C-methylisoflavones isosideroxylin（1）,6,8-dimethylgenistein（2） and their analogues（3-8） is established for the first time.The synthesis is realiz...A modular and efficient synthesis of the biologically significant C-methylisoflavones isosideroxylin（1）,6,8-dimethylgenistein（2） and their analogues（3-8） is established for the first time.The synthesis is realized in 7-8 steps in overall yields of 16%-24%from commercially inexpensive phloroglucinol and features a high yielding Vilsmeier-Haack reaction,Friedel-Crafts acylation,Gammill＇s protocol and Suzuki coupling as the pivotal transformations.Next,these compounds evaluated for their inhibitory potency on the production of nitric oxide（NO） in lipopolysaccharide（LPS）-activated RAW-264.7 cells as an indicator of anti-inflammatory activity.The results showed that all the compounds decreased NO production in a dose-dependent manner without marked cytotoxicity and IC_（50） values are found in the range of 10.17-33.88 μmol/L.Of note,compounds 3 followed by 1,7 and 8 show comparable inhibitory activity with positive control（N-monomethyl-L-arginine,L-NMMA）.展开更多
基金financially supported by industrial co-work program with Sun Chem(Sun Kyung Chemical Co.,South Korea)
文摘A modular and efficient synthesis of the biologically significant C-methylisoflavones isosideroxylin（1）,6,8-dimethylgenistein（2） and their analogues（3-8） is established for the first time.The synthesis is realized in 7-8 steps in overall yields of 16%-24%from commercially inexpensive phloroglucinol and features a high yielding Vilsmeier-Haack reaction,Friedel-Crafts acylation,Gammill＇s protocol and Suzuki coupling as the pivotal transformations.Next,these compounds evaluated for their inhibitory potency on the production of nitric oxide（NO） in lipopolysaccharide（LPS）-activated RAW-264.7 cells as an indicator of anti-inflammatory activity.The results showed that all the compounds decreased NO production in a dose-dependent manner without marked cytotoxicity and IC_（50） values are found in the range of 10.17-33.88 μmol/L.Of note,compounds 3 followed by 1,7 and 8 show comparable inhibitory activity with positive control（N-monomethyl-L-arginine,L-NMMA）.
