50259-93-3Relevant academic research and scientific papers
Unconventional Transformation of the Two Carbonyl Groups in 4,4′,5,5′-Tetrachloro-10 H,10′ H-[9,9′-bianthracenylidene]-10,10′-dione into Diallenes
Chen, Liangliang,Du, Mingxu,Jiang, Wenlin,Liu, Zitong,Tian, Jianwu,Zhang, Deqing,Zhang, Guanxin,Zhang, Xisha
, (2020)
The diallene-containing compound dACl-1 was unexpectedly obtained by the unconventional transformation of two carbonyl groups in 4,4′,5,5′-tetrachloro-10H,10′H-[9,9′-bianthracenylidene]-10,10′-dione into diallenes. In addition, the two 1-triisopropylsilyl
Straightforward Access to Anthrone Functionalized Benzylic Amines via Organocatalytic 1,2-Addition of Anthrones to Imines at Ambient Temperature
Das, Sumit,Bhowmik, Arup,Sarkar, Writhabrata,Mishra, Aniket,Deb, Indubhusan
, p. 4131 - 4142 (2021/03/09)
Activation of anthrone via benzylic deprotonation in the presence of triethylamine paves the way for the 1,2-addition reaction with imines to provide the desired functionalized anthrones in good to excellent yields under mild and operationally simple reaction conditions with a broad range of substrate scopes without using any external additives or toxic stoichiometric reagents.
Small molecule-induced degradation of the full length and V7 truncated variant forms of human androgen receptor
Dalal, Kush,Morin, Helene,Ban, Fuqiang,Shepherd, Ashley,Fernandez, Michael,Tam, Kevin J.,Li, Huifang,LeBlanc, Eric,Lack, Nathan,Prinz, Helge,Rennie, Paul S.,Cherkasov, Artem
, p. 1164 - 1173 (2018/09/12)
The androgen receptor (AR) is a hormone-activated transcription factor that regulates the development and progression of prostate cancer (PCa) and represents one of the most well-established drug targets. Currently clinically approved small molecule inhib
Benzylic Functionalization of Anthrones via the Asymmetric Ring Opening of Oxabicycles Utilizing a Fourth-Generation Rhodium Catalytic System
Loh, Charles C. J.,Fang, Xiang,Peters, Brendan,Lautens, Mark
supporting information, p. 13883 - 13887 (2015/09/28)
While anthrones exist as privileged scaffolds in bioactive molecules, the enantioselective functionalization of anthrones is surprisingly scarce in the literature, with no asymmetric transition metal catalyzed example to date. Herein, we report the first asymmetric transition metal catalyzed benzylic functionalization of anthrones through the rhodium(I) catalyzed desymmetrization of oxabicycles. As previously developed rhodium(I) systems were found to be unsuitable for this substrate, a new robust fourth-generation [Rh(cod)OH]2 based catalytic system was developed to address synthetic challenges in this protocol.
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.
Syntheses of anthraeenones. 1. Sodium dithionite reduction of peri-substituted anthracenediones
Prinz, Helge,Wiegrebe, Wolfgang,Mu?ller, Klaus
, p. 2853 - 2856 (2007/10/03)
The reaction of peri-substituted anthracenediones with sodium dithionite in dimethylformamide and water has been investigated. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 4,5-disubstituted 9(10H)-anthracenones and thus provides a route to anthracenones which are otherwise difficult to obtain. Many functional groups can be tolerated, the reaction is compatible with the presence of peri alkoxy groups and unsaturated side chains of the starting anthracenediones, and the reduction does not go beyond the anthracenone stage. However, the formation of anthracenones depends on the nature of the peri substituents. No products were obtained from the 1,8-dimethyl-substituted anthracene-dione and the parent compound with no substituents.
Unsymmetrically Substituted 1,8-Diarylanthracenes
House, Herbert O.,Hrabie, Joseph A.,VanDerveer, Don
, p. 921 - 929 (2007/10/02)
Unsymmetrically substituted 1,8-diarylanthracenes where the aryl rings are m-tolyl (5), o-tolyl (6), and 2,3-dimethylphenyl (7) have been synthesized; the barriers to aryl ring rotation in these hydrocarbons were found to be 5.3, 10.4, and 16.3 kcal/mol, respectively.Addition of either an acetoxyl (14) or a methyl (15) substituent at C-9 of the dixylylanthracene gave mixtures of cis and trans isomers that also exhibited rotation of an aryl ring within the temperature range 25-120 deg C.X-ray crystal structures for the cis- (14b) and trans- (14a) 9-acetoxydixylylanthracenes demonstrated significant distortion in the geometry of the anthracene ring, permitting rotation of the aryl rings with unexpected ease in solutions at temperatures above 100 deg C.
Reactions of the 1,8-Diphenylanthracene System
House, Herbert O.,Ghali, Nabih I.,Haack, John L.,VanDerveer, Don
, p. 1807 - 1817 (2007/10/02)
An improved synthesis of 1,8-diphenylanthracene (1) is described along with various reactions of this hydrocarbon, including electrophilic substitution reactions, oxidations, and addition of n-BuLi.The molecular geometry of a derivative, 10-bromo-1,8-diphenylanthracene (20), was determined by X-ray crystallography.Of the various routes explored for forming 9-substituted 1,8-diphenylanthracenes, only the addition of certain organometallic reagents to the 9-anthrone 10 was satisfactory.
