- Unique hydrogen bonds between 9-anthracenyl hydrogen and anions
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Unique hydrogen bonds of the 9-H of anthracene moieties in hosts 1 and 2 with fluoride and pyrophosphate ions were observed on the basis of the 1H NMR experiments. Furthermore, hosts 1 and 2 act as a colorimetric sensor and a fluorescent chemosensor for the recognition of fluoride ion, respectively.
- Kwon, Ji Young,Jang, Yun Jung,Kim, Sook Kyung,Lee, Keun-Hyeung,Kim, Jong Seung,Yoon, Juyoung
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- Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9,10-diones
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Telomerase is an attractive target for the design of new anticancer drugs. We have previously described a series of 1,4- and 2,6-difunctionalized amidoanthracene-9,10-diones that inhibit human telomerase via stabilization of telomeric G-quadruplex structures. The present study details the preparation of three further, distinct series of regioisomeric difunctionalized amidoanthracene-9,10-diones substituted at the 1,5-, 1,8-, and 2,7-positions, respectively. Their in vitro cytotoxicity and Taq DNA polymerase and human telomerase inhibition properties are reported and compared with those of their 1,4- and 2,6-isomers. Potent telomerase inhibition ((tel)IC50 values 1.3-17.3 μM) is exhibited within each isomeric series. In addition, biophysical and molecular modeling studies have been conducted to examine binding to the target G-quadruplex structure formed by the folding of telomeric DNA. These studies indicate that the isomeric diamidoanthracene-9,10-diones bind to the human telomeric G-quadruplex structure with a stoichiometry of 1:1. Plausible G-quadruplex-ligand complexes have been identified for each isomeric family, with three distinct modes of intercalative binding being proposed. The exact mode of intercalative binding is dictated by the positional placement of substituent side chains. Furthermore, in contrast to previous studies directed toward triplex DNA, it is evident that stringent control over positional attachment of substituents is not a necessity for effective telomerase inhibition.
- Perry, Philip J.,Reszka, Anthony P.,Wood, Alexis A.,Read, Martin A.,Gowan, Sharon M.,Dosanjh, Harvinder S.,Trent, John O.,Jenkins, Terence C.,Kelland, Lloyd R.,Neidle, Stephen
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- Syntheses and structures of hypervalent pentacoordinate carbon and boron compounds bearing an anthracene skeleton - Elucidation of hypervalent interaction based on X-ray analysis and DFT calculation
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Pentacoordinate and tetracoordinate carbon and boron compounds (27, 38, 50-52, 56-61) bearing an anthracene skeleton with two oxygen or nitrogen atoms at the 1,8-positions were synthesized by the use of four newly synthesized tridentate ligand precursors. Several carbon and boron compounds were characterized by X-ray crystallographic analysis, showing that compounds 27, 56-59 bearing an oxygen-donating anthracene skeleton had a trigonal bipyramidal (TBP) pentacoordinate structure with relatively long apical distances (ca. 2.38-2.46 A). Despite the relatively long apical distances, DFT calculation of carbon species 27 and boron species 56 and experimental accurate X-ray electron density distribution analysis of 56 supported the existence of the apical hypervalent bond even though the nature of the hypervalent interaction between the central carbon (or boron) and the donating oxygen atom was relatively weak and ionic. On the other hand, X-ray analysis of compounds 50-52 bearing a nitrogen-donating anthracene skeleton showed unsymmetrical tetracoordinate carbon or boron atom with coordination by only one of the two nitrogen-donating groups. It is interesting to note that, with an oxygen-donating skeleton, the compound 61 having two chlorine atoms on the central boron atom showed a tetracoordinate structure, although the corresponding compound 60 with two fluorine atoms showed a pentacoordinate structure. The B-O distances (av 2.29 A) in 60 were relatively short in comparison with those (av 2.44 A) in 59 having two methoxy groups on the central boron atom, indicating that the B-O interaction became stronger due to the electron-withdrawing nature of the fluorine atoms.
- Yamashita, Makoto,Yamamoto, Yohsuke,Akiba, Kin-Ya,Hashizume, Daisuke,Iwasaki, Fujiko,Takagi, Nozomi,Nagase, Shigeru
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- Designed synthesis of ferrocenylanthraquinones and their bifunctional electrochromic properties
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(Figure Presented) New bifunctional electrochromic systems were developed by combination of reductive anthraquinone with oxidative ferrocene redox systems. The resultant ferrocenylanthraquinones demonstrated enhanced stability in electrochromic performanc
- Sharmoukh,Ko, Kyoung Chul,Ko, Ju Hong,Jung, Ii Gu,Noh, Changho,Lee, Jin Young,Son, Seung Uk
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- Three anthracene-based bis-imidazolium salts: Synthesis, structure and recognition for 2,4-dinitrophenylhydrazine
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Three anthracene-based bis-imidazolium salts 1,8-bis [2’-(N-R-imidazoliumyl) acetamido]anthracene 2× (1: R = nBu, X = Cl?; 2: R = nBu, X = PF6 ?; 3: R = Et, X = PF6 ?) were prepared. The structure of 1 was demonstrated by X-ray analysis. The selective recognition of 2 (or 3) for some aromatic compounds (toluene, chlorobenzene, phenylamine, phenol, anisole, benzaldehyde, acetophenone, nitrobenzene, m-dinitrobenzene, 2,4-dinitrotoluene, 2,4-dinitrophenylhydrazine (DNP), trinitrophenol, o-nitrophenol, p-nitrotoluene) was investigated through fluorescence, ultraviolet, 1H NMR, HRMS and IR spectra at 25 °C. Compounds 2 (or 3) showed good selective recognition ability for DNP, and they could effectively distinguish DNP from other aromatic compounds. The association constants and detection limits of 2 and 3 were similar, which displayed sizes of side chains (nBu for 2 and Et for 3) had no remarkable effect on the recognition of DNP.
- Liu, Qingxiang,Yu, Shaocong,Zhao, Zhixiang,Zhang, Xiantao,Liu, Rui
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- Anthracene Bisureas as Powerful and Accessible Anion Carriers
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Synthetic anion carriers (anionophores) have potential as biomedical research tools and as treatments for conditions arising from defective natural transport systems (notably cystic fibrosis). Highly active anionophores that are readily accessible and eas
- Dias, Christopher M.,Valkenier, Hennie,Davis, Anthony P.
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- Organic cage inclusion crystals exhibiting guest-enhanced multiphoton harvesting
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Host-guest complexation is an important supramolecular route to materials. Clear design rules have been developed for complexation in solution. This has proved more challenging for solid-state host-guest co-crystals because they often exhibit polymorphism, leading many researchers to focus instead on bonded frameworks, such as metal-organic frameworks. Here, we report an anthracene-based organic cage (1) that forms isoskeletal host-guest co-crystals with five similarly sized solid organic guests. The co-crystals were designed using inexpensive computational methods to identify appropriate guests that have packing coefficients (PCs) ranging from 44% to 50%, coupled with consideration of the guest shape. By complexing highly emissive BODIPY guests into the host structure, we enhanced its two-photon excited photoluminescent properties by a factor of six. Our crystal design approach was also transferrable to hard-to-design ternary organic crystals that were accessed by inserting specific guests into different sized voids in the host.
- Cooper, Andrew I.,Cui, Peng,Jelfs, Kim E.,Little, Marc A.,Ning, Guo-Hong,Pang, Zhongfu,Pegg, James T.,Sazanovich, Igor V.,Towrie, Mike,Wei, Rong-Jia,Zhu, Qiang
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supporting information
p. 3157 - 3170
(2021/11/16)
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- Synthesis, structures and luminescence properties of N^C^N-coordinated platinum(II) complexes based on an anthracene core: A red shift and a twist
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1,8-Bis(2-pyridyl)anthracene HL2 is shown to act as a tridentate, N^C^N-coordinating ligand to platinum(II), undergoing metallation at position 9 of the anthracene. The structures of Pt(N^C^N-L2)Cl and of HL2 have been determined by X-ray diffraction. The complex features two 6-membered chelate rings and an N-Pt-N bite angle of 178.16(7)°, close to the “ideal” value of 180°. The attainment of this angle necessitates not only a twisting of the pyridyl rings relative to the anthracene, but also a remarkable twisting distortion of the anthracene unit itself. The complex is isomeric with the previously reported Pt(d8qb)Cl {d8qb = 1,3-di(8-quinolyl)benzene}. A new derivative of the latter has been prepared, PtL3Cl, featuring methyl substituents in the central benzene ring ortho to the quinolines. Like PtL2Cl, its structure shows twisting of the coordinated heterocycles relative to the plane of the central aromatic ring. The Pt(II) complex PtL1Cl of a related N^C^N-coordinating ligand featuring extended conjugation, benzo[1,2-h: 5,4 = h’]diquinoline HL1, has also been prepared following a previously described procedure. PtL1Cl is brightly phosphorescent in deoxygenated solution at ambient temperature, in the red region of the spectrum. The impressive photoluminescence quantum yield of 0.30 and long emission lifetime of 38 μs are indicative of a rigid structure with little excited state distortion. In contrast, PtL2Cl shows no detectable emission, probably due to the distorted nature of the structure leading to rapid non-radiative decay of the excited state. This result contrasts with the weak red emission displayed by the isomeric Pt(d8qb)Cl and its dimethylated derivative PtL3Cl.
- Gildea, Louise F.,Williams, J. A. Gareth,Wood, Emily A.,Yufit, Dmitry S.
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- Anthrabiimidazole salt compound and preparation method and application thereof
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The invention discloses a preparation method and use of an anthrabiimidazole salt compound. The preparation method comprises that 1, 8-dinitroanthraquinone as a raw material, sodium sulfide and sodiumhydroxide undergo a reaction in an organic solvent to produce 1, 8-diaminoanthraquinone, the reaction product, sodium borohydride and sodium hydroxide undergo a reaction to produce 1, 8-diaminomethylanthracene, the 1, 8-aminomethylanthracene, chloroacetyl chloride and triethylamine undergo a reaction to produce 1, 8-dichloroacetamidoanthracene, the 1, 8-dichloroacetamidoanthracene and 1-n-butylimidazole undergo a reaction under reflux to produce 1, 8-bis[1-n-butyl-imidazolylacetamido]anthracene chloride (1), and the 1, 8-bis[1-n-butyl-imidazolylacetamido]anthracene chloride and NH4PF6 are subjected to anion exchange so that 1, 8-bis[1-n-butyl-imidazolylacetamido]anthracene hexafluorophosphate (2) is obtained. The anthrabiimidazole salt compound is prepared through simple processes, has obvious fluorescence sensitization effects, is sensitive to some specific objects, can be used for preparation of a fluorescent molecular recognition system and is mainly used in the technical field offluorescent probes.
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Paragraph 0017; 0019
(2018/06/26)
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- POLYMERIZABLE DICHROIC DYES
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The present invention relates to new dichroic dyes, their composition with slave materials and their use for a dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel, which for instance find application as electro- optical or optical devices.
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- Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms
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Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and α-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.
- Ulatowski, Filip,Jurczak, Janusz
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p. 4235 - 4243
(2015/05/13)
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- A dinuclear ruthenium catalyst with a confined cavity: Selectivity in the addition of aliphatic carboxylic acids to phenylacetylene
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A dinuclear ruthenium catalyst with a rigid anthracene spacer shows excellent regio- and stereo-selectivity in the atom-economic addition of aliphatic carboxylic acids to phenylacetylene, producing exclusively anti-Markovnikov enol-esters with high E/Z ratios of the isomers.
- Cheung, Kwong-Chak,Wong, Wing-Leung,So, Ming-Him,Zhou, Zhong-Yuan,Yan, Siu-Cheong,Wong, Kwok-Yin
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supporting information
p. 710 - 712
(2013/03/13)
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- Design, synthesis and evaluation of telomerase inhibitory, hTERT repressing, and anti-proliferation activities of symmetrical 1,8-disubstituted amidoanthraquinones
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A series of symmetrical disubstituded 1,8-diamidoanthraquinones were synthesized and evaluated for anti-proliferation, telomerase inhibitory by TRAP assay, and hTERT expression by SEAP assay. All of the compounds tested, except for compounds 3a and 3s were selected by the NCI screening system. In addition, compounds 4e and 4k exhibited inhibitory effects on telomerase activity. Taken together, our findings indicated that the analysis of cytotoxicity and telomerase inhibition might provide information applicable for further developing potential telomerase targeting strategy.
- Lee, Chia-Chung,Huang, Kuo-Feng,Chang, Deh-Ming,Hsu, Jung-Jung,Huang, Fong-Chun,Shih, Kai-Ning,Chen, Chun-Liang,Chen, Tsung-Chih,Chen, Ruei-Huei,Lin, Jing-Jer,Huang, Hsu-Shan
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scheme or table
p. 102 - 112
(2012/07/13)
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- Synthesis, characterization, and cyclometalation studies of benzo[1,2-h: 5,4-h′]diquinolines with palladium and platinum
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Benzo[1,2-h: 5,4-h′]diquinoline(1a) represents a new family of tridentate NCN pincer ligand. We report the synthesis of the parent ligand (1a) and its derivatives (1b R = Me, 1c R = t-Butyl, 1d R = Phenyl). The ligands were characterized by 1H and 13C NMR, as well as mass spectral analysis, and X-ray structural determination. They readily undergo cyclometalation with LiPdCl4, Pd(OAc)2, and K 2PtCl4 to form the cyclometalated Pd(NCN)Cl (2a-c, 3a), and Pt(NCN)Cl (4a) pincer complexes. These complexes have been characterized through NMR, and mass spectrometry. PdNCNCl (2a) structure was determined by single crystal X-ray diffraction. Complex 2a has shown to catalyze the Heck coupling reaction between bromobenzene and n-butylacyrlate in NMP at 140 °C, TON of 2506 were observed.
- Young, Kenneth J.H.,Bu, Xianhui,Kaska, William C.
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scheme or table
p. 3992 - 3997
(2012/01/03)
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- ANTI-CANCER COMPOUND AND MANUFACTURING METHOD THEREOF
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Anti-cancer compounds and manufacturing methods thereof are disclosed. The anti-cancer compounds are 1,8-diamidoanthraquinone derivatives with amino compounds. The manufacturing method includes the steps of: add 1,8-bis(chloroacetamido)anthraquinone or 1,8-bis(3-chloropropionamido)-anthraquinone with amino compounds, catalysts, and dehydrated dimethylformamide (DMF) to form a mixture and react with one another. Then by purification and recrystallization, the anti-cancer compounds are obtained. The anti-cancer compounds of the present invention are compounds with whole new structure that overcome serious cardiac toxicity of the conventional anti-cancer drug-doxorubincin.
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Page/Page column 5
(2010/06/19)
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- Synthesis and evaluation of a pseudocyclic tristhiourea-based anion host
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A novel methodology for the evaluation of receptor arrangement in structurally flexible anion chemosensors was developed and applied to map the binding site of a new pseudocyclic tristhiourea chemosensor (6). The syntheses of 6 and related macrocyclic chemosensor 10 (a model of the folded monomeric structure of 6) are reported. Both chemosensors were evaluated by titration with a variety of structurally different anions in CH3Cl and DMSO, showing a common preference for F-, CH3CO2 -, and H2PO4-. However, within this group of anions, the binding patterns of the chemosensors differed, indicating dissimilarity in the arrangement of the binding sites of 6 and 10.
- Dahan, Adi,Ashkenazi, Tali,Kuznetsov, Vladimir,Makievski, Svetlana,Drug, Eyal,Fadeev, Ludmila,Bramson, Maayan,Schokoroy, Sari,Rozenshine-Kemelmakher, Emily,Gozin, Michael
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p. 2289 - 2296
(2008/02/01)
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- A facile method for preparing substituted 1-aminoanthraquinones
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An efficient and simple preparation of α-substituted aminoanthraquinones using 2,2,-dialkoxyethylamines is described.
- Wormser,Sardessai,Abramson
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p. 3211 - 3222
(2007/10/02)
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- Process for the preparation of 1-acylamino-5(8)-chloroanthraquinones
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The invention relates to a novel process for the preparation of 1-acylamino-5(8)-chloroanthraquinones, which are starting materials for the preparation of vat dyes. It is characterized in that 1,5(8)-dichloroanthraquinones is reacted with ammonia at temperatures of 190° to 240° C., the amino groups in the reaction mixture are completely acylated and the more sparingly soluble diacylaminoanthraquinone is separated off from the more readily soluble monoacylaminochloroanthraquinone. The new process yields reaction products which are purer and cheaper than those which are obtained by conventional methods. Moreover there are smaller waste water problems.
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- Preparation of aminoanthraquinones from nitroanthraquinones
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In the reaction of a nitroanthraquinone with ammonia in a solvent at elevated temperature to produce the corresponding aminoanthraquinone, the improvement which comprises effecting the reaction in the presence of an ammonium halide. Advantageously, the nitroanthraquinone is an α-nitroanthraquinone, the ammonium halide is at least one of ammonium chloride and ammonium bromide, and the solvent comprises at least one member selected from the group consisting of water, nitrobenzene, a glycol, an acid amide and sulfolane.
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