76678-63-2Relevant academic research and scientific papers
Synthesis, antiprolife ativeactivity and inhibition of tubulinpolymerization by 1,5-and 1,8-disubstituted 10H-anthracen-9-onesbearinga 10-benzylidene or 10-(2-oxo-2-phenylethylidene) moiety
Nickel, Holger C.,Schmidt, Peter,B?hm, Konrad J.,Baasner, Silke,Müller, Klaus,Gerlach, Matthias,Unger, Eberhard,Günther, Eckhard G.,Prinz, Helge
experimental part, p. 3420 - 3438 (2010/08/20)
A novel series of 1,5-and 1,8-disubstituted 10-benzylidene-10H-anthracen-9- ones and 10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones was synthesized to assess the substituent effects on biological activity. The 3-hydroxy-2,4- dimethoxy-benzylidene analogue 16h displayed strong antiproliferative activity against several tumor cell lines,including multi-drug resistant phenotypes. Flow cytometric studies showed that KB/HeLa cells treated by elected compounds were arrested in the G2/M phases of the cell cycle. Among the compounds tested for inhibition of tubulin polymerization,14 compounds proved to be exceptionally active with IC50 values 1 mM. In the 1,5-dichloro-derived series of benzy-lideneanthracenones,E/Z isomers were separated and biological effects were monitored. We found that the olefinic geometry had no significant effect on biological activity. Furthermore,the E isomeric 1,5-dichloro-substituted phenacylidenes entirely proved to be more potent inhibitors of tubulin polymerization than the recently described 10-(2-oxo-2-phenylethylidene)-10H- anthracen-9-ones. In conclusion,the present study improves understanding of the action of anthracenone-based tubulin polymerization inhibitors and contributes to the design of further potent anti-tubulin drugs.
Biogenetic-type Synthesis of (+/-)-Phyllodulcin, a Sweet Principle of Hydrangea serrata Seringe var. thunbergii Sugimoto (Studies on the β-Carbonyl Compounds connected with the β-Polyketides. VI)
Takeuchi, Naoki,Murase, Masayuki,Ochi, Kazue,Tobinaga, Seisho
, p. 3013 - 3019 (2007/10/02)
A biogenetic-type synthesis of (+/-)-phyllodulcin (2), a sweet principle of Hydrangea serrata SERINGE var. thunbergii SUGIMOTO, from 3-(3-benzyloxy-4-methoxyphenyl)-2-propenal (7) modelled on the polyketide mode of biosynthesis is described.Keywords - β-p
