1143-38-0Relevant articles and documents
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
, p. 13883 - 13887 (2015)
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.
Syntheses of anthraeenones. 1. Sodium dithionite reduction of peri-substituted anthracenediones
Prinz, Helge,Wiegrebe, Wolfgang,Mu?ller, Klaus
, p. 2853 - 2856 (1996)
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.
1,8-Substituted anthraquinones, anthrones and bianthrones as potential non-azole leads against fungal infections
Jalab, Murhaf,Critchley, Megan E.,Taylor, Charlotte M.,Lawrence, Clare L.,Smith, Robert B.
, (2019)
The synthesis of a variety of 1,8-substituted anthraquinones, anthrones and bianthrones and their potential as antifungal agents is evaluated. Preliminary screening against Schizosaccharomyces pombe (S. pombe), a fission yeast, and Saccharomyces cerevisiae (S. cerevisiae), a budding yeast, is reported. Both these yeast species demonstrate close homologue to a number of pathogenic fungi.
Synthesis of a Monomer for Two-Dimensional Polymerization under Technically Feasible Conditions
Tanner, Philipp,Maier, Gerhard,Schlüter, A. Dieter
, (2018)
The synthesis of a promising 2D polymer uses the double decker rotor-shaped monomer 1, containing three anthracene moieties. To accelerate the development of the field of 2D polymers, this monomer was selected for scale-up that would allow its synthesis to be performed on the kg scale under technical conditions. This goal was achieved in collaboration with Polymaterials AG, Kaufbeuren, Germany. Not only was the synthetic route shortened, but each and every aspect of the remaining steps was streamlined so as to render them applicable to technical conditions. This involved the entire sequence to be adapted to metal instead of glass reactors and to a number of safety and toxicity concerns. Additionally, not only the utilization of the reactors had to meet strict efficiency requirements, but also the work-up procedures had to be facile. The whole sequence was then tested for feasibility under realistic conditions at Polymaterials AG. While this test afforded 130?g of monomer 1, it has the clear potential for the kg scale, supposed the safety equipment for the hydrogen evolution for the conversion of compound 2a?–?3 is available.
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)
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.
Design, synthesis, and time-gated cell imaging of carbon-bridged triangulenium dyes with long fluorescence lifetime and red emission
Rosenberg,Rostgaard,Liao,Madsen,Martinez,Vosch,Laursen
, p. 3122 - 3130 (2018)
Time-resolved fluorescence offers many advantages over normal steady-state detection and becomes increasingly important in bioimaging. However, only very few fluorophores with emission in the visible range and fluorescence lifetimes above 5 ns are available. In this work, we prepare a series of new aza/oxa-triangulenium dyes where one of the usual oxa or aza bridges is replaced by an isopropyl bridge. This leads to a significant redshift of fluorescence with only moderate reductions of quantum yields and a unique long fluorescence lifetime. The fluorescence of the isopropyl bridged diazatriangulenium derivative CDATA+ is red-shifted by 50 nm (1400 cm-1) as compared to the oxygen-bridged DAOTA+ chromophore and has intense emission in the red region (600-700 nm) with a quantum yield of 61%, and a fluorescence lifetime of 15.8 ns in apolar solution. When the CDATA+ dye is used as cell stain, high photostability and efficient time-gated cell imaging is demonstrated.
Method for treating psoriasis using selected phosphorylase kinase inhibitor and additional compounds
-
, (2008/06/13)
An improved method of treating psoriasis involves controlling the enhanced proliferation and terminal differentiation of psoriatic epidermis through the activity of epidermal phosphorylase kinase. In general, the method involves contacting psoriatic epidermal cells with a combination of substances affecting the activity of phosphorylase kinase. The combination can be: (1) a calmodulin inhibitor together with a stimulator of cAMP-dependent protein kinase II, (2) a calmodulin inhibitor together with a calcium channel blocker; (3) a stimulator of cAMP-dependent protein kinase II together with a calcium channel blocker; or (4) a calmodulin inhibitor together with a calcium channel blocker and a stimulator of cAMP-dependent protein kinase II. Alternatively, a selective phosphorylase kinase inhibitor such as curcumin can be administered, alone or with an agent such as vitamin D 3 or an analogue thereof, etretinate, diltiazem, or anthralin. The invention also includes pharmaceutical compositions.
10-α-aminoacyl-9(10H)-anthracenones: Inhibition of 12(S)-HETE biosynthesis and HaCaT cell growth
Mueller, Klaus,Breu, Klaus
, p. 31 - 35 (2007/10/03)
1,8-Dihydroxy-9(10H)-anthracenones with a 10-α-aminoacyl group were synthesized using either a mixed-anhydride coupling method or Boc-protected oxazotidinediones. The novel anthracenones were evaluated as inhibitors of the biosynthesis of 12(S)-hydroxyeicosatetraenoic acid (12(S)-HETE) in epidermal homogenate of mice and for inhibition of the growth of HaCaT keratinocytes. These cells were also tested for their susceptibility for the action of the most potent members of this series on plasma membrane integrity, in order to confirm that inhibition of cell growth is not a result of membrane damage induced by prooxidants released from anthracenones. Hydroxyl-radical generation as measure of the prooxidant potential of the compounds was determined by deoxyribose degradation. The most potent analogues of this series were equally potent as anthralin against 12(S)-HETE biosynthesis and keratinocyte proliferation, while oxygen-radical generation and the resulting damage to cell membrane was strongly reduced as compared to the antipsoriatic drug.
Syntheses of anthracenones. 3. Revised preparative route to 10-Benzoyl-1,8-dihydroxy-9(10H)-anthracenones
Prinz, Helge,Wiegrebe, Wolfgang,Müller, Klaus
, p. 2861 - 2864 (2007/10/03)
The acylation of anthralin (1,8-dihydroxy-9(10H)-anthracenone) with acetylsalicylic acid chloride in toluene and collidine was found to give the O-acylated product, rather than 10-(acetylsalicyl)-anthralin. A procedure is described for benzoylation of anthralin in the 10-position which involves reaction of 1,8-diacetoxy-9(10H)-anthracenone with benzoyl chloride and sodium hydride in THF followed by hydrolysis of an intermediate enol ester. Furthermore, when benzoyl chloride and DMF were used for the acylation of anthralin, a Vilsmeier-type reaction was observed leading to a novel enamine derivative of anthralin which was hydrolyzed or benzoylated to an enol or enol ester, respectively.
