Synthesis of flavonoid analogues as scaffolds for natural product-based combinatorial libraries.
The design and synthesis of flavonoid analogues as combinatorial scaffolds is reported. Using commercially available materials, we synthesized chalcones with fluoro and carboxy groups. Nitration of these compounds generated highly functionalized flavonoid scaffolds with an o-fluoronitrobenzene template. Subsequent cyclizations of these chalcones resulted in the formation of several flavone and flavonone scaffolds. One of the flavonones was chosen as the scaffold to synthesize flavonoid derivatives on the solid phase. A series of flavonoid derivatives were obtained in high yields, which demonstrates that these highly functionalized scaffolds can be used in the synthesis of natural product-based combinatorial libraries for drug discovery.
Yao
Nianhuan
N
Division of Hematology & Oncology, Department of Internal Medicine, UC-Davis Medical Center, 4501 X Street, Sacramento, California 95817, USA.
Song
Aiming
A
Wang
Xiaobing
X
Dixon
Seth
S
Lam
Kit S
KS
D001688:Biological Products / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D016208:Databases, Factual; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure
D001688:Biological Products; D005419:Flavonoids