364-55-6Relevant academic research and scientific papers
Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction
Kaishap, Partha P.,Duarah, Gauri,Sarma, Bipul,Chetia, Dipak,Gogoi, Sanjib
, p. 456 - 460 (2018/02/21)
The first decarbonylative insertion of an alkyne through C?H/C?C activation of six-membered compounds is reported. The Ru-catalyzed reaction of 3-hydroxy-2-phenyl-chromones with alkynes works most efficiently in the presence of the ligand PPh3 to provide spiro-indenebenzofuranones. Unlike previously reported metal-catalyzed decarbonylative annulation reactions, in the present decarbonylative annulation reaction, the annulation occurs before extrusion of carbon monoxide.
The rearrangement of tosylated flavones to 1′-(alkylamino)aurones with primary amines
Kandioller, Wolfgang,Kubanik, Mario,Bytzek, Anna K.,Jakupec, Michael A.,Roller, Alexander,Keppler, Bernhard K.,Hartinger, Christian G.
, p. 8953 - 8959 (2015/11/02)
A rearrangement of 3-tosylflavone to the corresponding 1′-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1′-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed.
Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin
Dias, Tatiana A.,Duarte, Cecília L.,Lima, Cristovao F.,Proen?a, M. Fernanda,Pereira-Wilson, Cristina
, p. 500 - 510 (2013/10/01)
A series of chalcone and flavonol derivatives were synthesized in good yield by an eco-friendly approach. A pharmacological evaluation was performed with the human colorectal carcinoma cell line HCT116 and revealed that the anticancer activity of flavonols was higher when compared with that of the respective chalcone precursors. The antiproliferative activity of halogenated derivatives increases as the substituent in the 3- or 4-positon of the B-ring goes from F to Cl and to Br. In addition, halogens in position 3 enhance anticancer activity in chalcones whereas for flavonol derivatives the best performance was registered for the 4-substituted derivatives. Flow cytometry analysis showed that compounds 3p and 4o induced cell cycle arrest and apoptosis as demonstrated by increased S, G2/M and sub-G1 phases. These data were corroborated by western blot and fluorescence microscopy analysis. In summary, halogenated chalcones and flavonols were successfully prepared and presented high anticancer activity as shown by their cell growth and cell cycle inhibitory potential against HCT116 cells, superior to that of quercetin, used as a positive control.
Structure-Activity relationships of targeted RuII(η 6- P -Cymene) anticancer complexes with flavonol-Derived ligands
Kurzwernhart, Andrea,Kandioller, Wolfgang,B?chler, Simone,Bartel, Caroline,Martic, Sanela,Buczkowska, Magdalena,Mühlgassner, Gerhard,Jakupec, Michael A.,Kraatz, Heinz-Bernhard,Bednarski, Patrick J.,Arion, Vladimir B.,Marko, Doris,Keppler, Bernhard K.,Hartinger, Christian G.
, p. 10512 - 10522 (2013/02/22)
RuII(arene) complexes have been shown to be promising anticancer agents, capable of overcoming major drawbacks of currently used chemotherapeutics. We have synthesized RuII(η6-arene) compounds carrying bioactive flavonol ligands with the aim to obtain multitargeted anticancer agents. To validate this concept, studies on the mode of action of the complexes were conducted which indicated that they form covalent bonds to DNA, have only minor impact on the cell cycle, but inhibit CDK2 and topoisomerase IIα in vitro. The cytotoxic activity was determined in human cancer cell lines, resulting in very low IC50 values as compared to other RuII(arene) complexes and showing a structure-activity relationship dependent on the substitution pattern of the flavonol ligand. Furthermore, the inhibition of cell growth correlates well with the topoisomerase inhibitory activity. Compared to the flavonol ligands, the RuII(η6-p-cymene) complexes are more potent antiproliferative agents, which can be explained by potential multitargeted properties.
