50259-92-2Relevant 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
scheme or table, 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.
Synthesis and pharmaceuticals of novel 9-substituted-1, 5-dichloroanthracene analogs
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, (2008/06/13)
The invention relates to novel anthracene compounds useful in the treatment of allergic, inflammatory conditions, tumor conditions and therapeutic compositions containing such compounds. The compounds of the present invention are 9-acyloxy-substituted 1,5-dichloroanthracene or analogs thereof. According to the practice of the invention, there are provided 9-acyloxy substituted 1,5-dichloroanthracene compounds according to formula III: wherein R represents a straight or branched chain alkyl group having 1 to 6 carbons which may be substituted with one or more groups of R1, or R represents phenyl or benzyl which may be substituted with one or two groups of R2; wherein R1 is selected from the group consisting of halogen, —NO2, —OCH3, OCH2CH3, and —OCH2CH2CH3; and wherein R2 is selected from the group consisting of a straight or branched chain alkyl group having 1 to 4 carbons, halogen, —NO2, —OCH3, —OCH2CH3, and —OCH2CH2CH3.
Studies on anthracenes. 1. Human telomerase inhibition and lipid peroxidation of 9-acyloxy 1,5-dichloroanthracene derivatives
Huang, Hsu-Shan,Hwang, Jing-Min,Jen, Yee-Min,Lin, Jing-Jer,Lee, Kung-Yuan,Shi, Chang-Hsin,Hsu, Hsien-Chin
, p. 969 - 973 (2007/10/03)
The synthetically useful approaches to 9-acyloxy 1,5-dichloroanthracene derivatives are reported. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 1,5-dichloro-9(10H)-anth
