95273-01-1Relevant academic research and scientific papers
Synthesis and biological activity of flavanone derivatives
Shi, Lei,Feng, Xiu E,Cui, Jing Rong,Fang, Lian Hua,Du, Guan Hua,Li, Qing Shan
scheme or table, p. 5466 - 5468 (2011/01/03)
A series of new flavanone derivatives of farrerol was synthesized by a convenient method. The in vitro anti-tumor activity of these compounds was evaluated against human Bel-7402, HL-60, BGC-823 and KB cell lines, the protein tyrosine kinase (PTK) inhibitor activity was also tested. Their cytoprotective activity was tested using hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells. Their in vitro anti-atherosclerosis activity was tested on vascular smooth muscle cells by the MTT method using tetrandrine as a positive contrast drug. The structures of all compounds synthesized were confirmed by 1H, 13C NMR and ESI-MS. Most of the compounds exhibited good pharmacological activity and the preliminary structure-activity relationships were described.
Asymmetric cyclization of 2′-hydroxychalcones to flavanones: Catalysis by chiral Bronsted acids and bases
Dittmer, Claudia,Raabe, Gerhard,Hintermann, Lukas
, p. 5886 - 5898 (2008/04/13)
The asymmetric cyclization of 2′-hydroxychalcones to flavanones is a basic, enzyme-catalyzed step in the biosynthesis of flavonoid natural products, but poses a long-standing problem for asymmetric catalysis with small molecule catalysts. Earlier claims concerning the realization of an asymmetric flavanone synthesis by means of camphorsulfonic acid as chiral Bronsted acid catalysts were reinvestigated using accurate HPLC methods for quantification of enantiomer ratios. The previous claims of asymmetric induction were thus shown to be untenable. On the other hand, cinchona alkaloids serve as chiral Bronsted base mediators for the asymmetric cyclization of either 6′-substituted 2′-hydroxychalcones or 2′,6′- dihydroxychalcones. 2′,6′-Dihydroxy-4,4′-dimethoxychalcone, for instance, cyclized to give the naturally occurring naringenin-4′,7- dimethyl ether in up to 64 % ee at 81 % conversion. The catalysis shows a marked dependency of the enantiomeric excess of the product on the catalyst, solvent and reactant concentration. Based on these successful examples of asymmetric cyclizations of 2′-hydroxychalcones to flavanones, requirements for more active asymmetric catalysts can be defined. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
