- Cation Complexation, Photochromism, and Reversible Ion-Conducting Control of Crowned Spironaphthoxazine
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A spironaphthoxazine derivative incorporating a monaza-12-crown-4 moiety at the 5'-position has been designed as a light-resistant, cation-complexable photochromic compound.Complexation of alkali metal ions by the crown moiety in the crowned spironapthoxazine allows the spironaphthoxazine skeleton to isomerize to its corresponding open colored form, even under dark conditions.Specifically, Li(1+) complexation greatly stabilizes the open colored form due to the intramolecular interaction between its oxo group and crown-complexed cation, as well as the selective Li(1+) complexation of its 12-crown-4 moiety.Taking advantage of the high Li(1+) selectivity in the cation-induced isomerization of crowned spironaphthoxazine, the thermal stability of the open colored form can be modulated continuously by added Li(1+) concentrations.Even in the presence of the metal ion, UV- and visible-light irradiation led to futher isomerization to the open form and back-isomerization to the initial closed form, respectively.Photoisomerization of crowned spironaphthoxazine to its open form promoted Li(1+) binding due to the additional axial interaction with the crown-complexed Li(1+), while that back to the closed form attenuated the cation binding.The photoinduced change in the cation-binding ability of crowned spironaphthoxazine, which possesses high light-fatigue resistance, has led to a highly reversible, photochemical switching system of ionic conduction.
- Kimura, Keiichi,Kaneshige, Masayuki,Yamashita, Takashi,Yokoyama, Masaaki
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Read Online
- A novel method for the synthesis of (R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid by asymmetric oxidative coupling of a chiral β-naphthol derivative catalyzed by CuCl
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Asymmetric oxidative coupling of (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 1 catalyzed by CuCl afforded (S,S,R)-2,2′-dihydroxy-3,3′-bis(2-methoxycarbonyl-1- pyrrolidinylcarbonyl)-1,1′-binapthalene 2 with diastereomeric excess up to 65.9%. (R)-BINOL-3,3′-diacid 3 was obtained in 30% overall yield and 97% e.e. by separating the diastereomers and hydrolyzing 2.
- Xin, Zhuo-qun,Da, Chao-shan,Dong, Shou-liang,Liu, Da-xue,Wei, Jie,Wang, Rui
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Read Online
- Method for preparing naphthol AS-OL by micro-channel continuous method
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The invention discloses a method for preparing naphthol AS-OL by a micro-channel continuous method. The method comprises the following specific steps: carrying out an N-acylation reaction in a micro-channel reactor by using 2-hydroxy-3-naphthoic acid and o-toluidine as raw materials to generate N-acyl arylamine naphthol AS-OL, wherein the 2-hydroxy-3-naphthoic acid is a weak acylation reagent andneeds to generate acyl chloride with a dehydrating agent phosphorus trichloride so as to further be subjected to amidation with the o-toluidine. The method comprises: feeding material into a micro-channel reactor through a metering pump, uniformly mixing, carrying out an amidation reaction at 80-150 DEG C for 5-30 minutes, collecting the effluent of the micro-channel reactor, and carrying out steam distillation, water washing, filtering and other steps to obtain the naphthol AS-OL. According to the invention, the yield of the method is 90-96%; and the method is easy to operate and control, short in production period, capable of realizing multiple amplification through parallel connection, free of amplification effect, capable of reducing environmental pollution, few in obtained by-products, high in selectivity, good high product quality and particularly suitable for industrial production.
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Paragraph 0018-0019
(2020/05/02)
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- PIGMENT DISPERSANT AND PIGMENT COMPOSITION, COLORED COMPOSITION AND COLOR FILTER USING THE SAME
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PROBLEM TO BE SOLVED: To provide a pigment dispersant showing extremely excellent characteristics in improving dispersibility of a pigment, which highly achieves both a contrast ratio and luminance of a coating film (color filter) when the color filter is
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Paragraph 0185-0186
(2020/07/31)
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- Solvatofluorochromic flavonoid dyes with enlarged transition dipole moments enable the ratiometric detection of methanol in commercial biodiesel with improved sensitivities
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Detection of methanol in commercial biodiesel is essential to evaluate the fuel quality associated with the matter of driving safety. Compared to the standard GC method, the fluorescent detection method for methanol is much simpler and faster, but still u
- Du, Bing,Huang, Yingying,Liu, Bin,Qin, Tianyi,Xu, Hanhong,Xun, Zhiqing,Yao, Guangkai,Zhao, Chen
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supporting information
p. 16808 - 16814
(2020/12/30)
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- Azo pigment, a coloring agent for a color filter, a colored composition for color filter
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[A] (heat resistance, light resistance) has excellent durability, less foreign film, not only a good storage stability or dye transfer, high luminance, color composition for color filter of the same color when expressed in the film thickness. [Solution] a
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Paragraph 0190; 0191
(2019/07/18)
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- SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway
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Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.
- Chae, Hee-Don,Cox, Nick,Capolicchio, Samanta,Lee, Jae Wook,Horikoshi,Kam, Sharon,Ng, Andrew A.,Edwards, Jeffrey,Butler, Tae-León,Chan, Justin,Lee, Yvonne,Potter, Garrett,Capece, Mark C.,Liu, Corey W.,Wakatsuki, Soichi,Smith, Mark,Sakamoto, Kathleen M.
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supporting information
p. 2307 - 2315
(2019/06/27)
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- AZO PIGMENT, COLOR FILTER COLORANT, COLORING COMPOSITION, AND COLOR FILTER
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PROBLEM TO BE SOLVED: To provide a color filter coloring composition which is excellent in heat resistance and light resistance, causes few particles in a coating and has good storage stability, and in addition has a high luminance and a high contrast ratio. SOLUTION: An azo pigment comprises a compound represented by a formula (1) in the figure and a monoazo compound not having one of the azo groups in the formula (1). [R1 is a halogen atom, a substituted/unsubstituted alkyl group, or a substituted/unsubstituted alkoxyl group; R2 and R3 are each independently H, a substituted/unsubstituted alkyl group, or a substituted/unsubstituted phenyl group; and X1 to X4 are each independently H, a substituted/unsubstituted alkyl group, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, or a halogen atom.] SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0199-0200
(2019/12/25)
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- AZO PIGMENT, COLOR FILTER COLORANT, COLORING COMPOSITION, AND COLOR FILTER
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PROBLEM TO BE SOLVED: To provide a color filter coloring composition which is excellent in fastness such as heat resistance and light resistance, causes few particles in a coating and has good storage stability, and in addition has a high luminance and a
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Paragraph 0233-0234
(2020/01/07)
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- Black azo-metal complex, photosensitive resin compositions containing thereof and cured films prepared using the composition
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The present invention relates to a black azo-metal complex, a photosensitive resin composition containing the same and a color filter prepared by using the same, wherein the black azo-metal complex of the present invention has excellent thermal stability, chemical resistance and solubility, so that the photosensitive resin composition and the color filter using the same have excellent optical properties such as color retention rate, optical density and surface resistance.COPYRIGHT KIPO 2018
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Paragraph 0127-0131; 0141-0144
(2018/07/28)
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- Azo pigment, a coloring agent for a color filter, a color filter and a bonding composition
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An object of the present invention is to provide a coloring composition for a color filter which is excellent in not only heat resistance and light resistance, but also has a small amount of foreign matter in a coating film, good storage stability, and hi
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Paragraph 0175-0176
(2018/09/25)
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- Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents
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A critical question in natural product-based drug discovery is how to translate the product into drug-like molecules with optimal pharmacological properties. The generation of natural product-inspired scaffold diversity is an effective but challenging strategy to investigate the broader chemical space and identify promising drug leads. Extending our efforts to the natural product evodiamine, a diverse library containing 11 evodiamine-inspired novel scaffolds and their derivatives were designed and synthesized. Most of them showed good to excellent antitumor activity against various human cancer cell lines. In particular, 3-chloro-10-hydroxyl thio-evodiamine (66c) showed excellent in vitro and in vivo antitumor efficacy with good tolerability and low toxicity. Antitumor mechanism and target profiling studies indicate that compound 66c is the first-in-class triple topoisomerase I/topoisomerase II/tubulin inhibitor. Overall, this study provided an effective strategy for natural product-based drug discovery. (Figure Presented).
- Wang, Shengzheng,Fang, Kun,Dong, Guoqiang,Chen, Shuqiang,Liu, Na,Miao, Zhenyuan,Yao, Jianzhong,Li, Jian,Zhang, Wannian,Sheng, Chunquan
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p. 6678 - 6696
(2015/09/07)
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- PIGMENT DISPERSANT, PIGMENT COMPOSITION AND PIGMENT COLORANT
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PROBLEM TO BE SOLVED: To provide a pigment dispersant which can significantly improve the fluidity of an ink, a coating composition or the like containing a pigment and can produce a colored article showing excellent glossiness and clarity. SOLUTION: Ther
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Paragraph 0055
(2018/11/24)
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- Novel TypeII Fatty Acid Biosynthesis (FAS II) Inhibitors as Multistage Antimalarial Agents
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Malaria is a potentially fatal disease caused by Plasmodium parasites and poses a major medical risk in large parts of the world. The development of new, affordable antimalarial drugs is of vital importance as there are increasing reports of resistance to the currently available therapeutics. In addition, most of the current drugs used for chemoprophylaxis merely act on parasites already replicating in the blood. At this point, a patient might already be suffering from the symptoms associated with the disease and could additionally be infectious to an Anopheles mosquito. These insects act as a vector, subsequently spreading the disease to other humans. In order to cure not only malaria but prevent transmission as well, a drug must target both the blood- and pre-erythrocytic liver stages of the parasite. P.falciparum (Pf) enoyl acyl carrier protein (ACP) reductase (ENR) is a key enzyme of plasmodial typeII fatty acid biosynthesis (FASII). It has been shown to be essential for liver-stage development of Plasmodium berghei and is therefore qualified as a target for true causal chemoprophylaxis. Using virtual screening based on two crystal structures of PfENR, we identified a structurally novel class of FAS inhibitors. Subsequent chemical optimization yielded two compounds that are effective against multiple stages of the malaria parasite. These two most promising derivatives were found to inhibit blood-stage parasite growth with IC50 values of 1.7 and 3.0μM and lead to a more prominent developmental attenuation of liver-stage parasites than the gold-standard drug, primaquine.
- Schrader, Florian C.,Glinca, Serghei,Sattler, Julia M.,Dahse, Hans-Martin,Afanador, Gustavo A.,Prigge, Sean T.,Lanzer, Michael,Mueller, Ann-Kristin,Klebe, Gerhard,Schlitzer, Martin
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p. 442 - 461
(2013/08/25)
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- Structure-activity relationship studies of naphthol AS-E and its derivatives as anticancer agents by inhibiting CREB-mediated gene transcription
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CREB (cyclic AMP-response element binding protein) is a downstream transcription factor of a multitude of signaling pathways emanating from receptor tyrosine kinases or G-protein coupled receptors. CREB is not activated until it is phosphorylated at Ser133 and its subsequent binding to CREB-binding protein (CBP) through kinase-inducible domain (KID) in CREB and KID-interacting (KIX) domain in CBP. Tumor tissues from various organs present higher level of expression and activation of CREB. Thus CREB has been proposed as a promising cancer drug target. We previously described naphthol AS-E (1a) as a small molecule inhibitor of CREB-mediated gene transcription in living cells. Here we report the structure-activity relationship (SAR) studies of 1a by modifying the appendant phenyl ring. All the compounds were evaluated for in vitro inhibition of KIX-KID interaction, cellular inhibition of CREB-mediated gene transcription and inhibition of proliferation of four cancer cell lines (A549, MCF-7, MDA-MB-231 and MDA-MB-468). SAR indicated that a small and electron-withdrawing group was preferred at the para-position for KIX-KID interaction inhibition. Compound 1a was selected for further biological characterization and it was found that 1a down-regulated the expression of endogenous CREB target genes. Expression of a constitutively active CREB mutant, VP16-CREB in MCF-7 cells rendered the cells resistant to 1a, suggesting that CREB was critical in mediating its anticancer activity. Furthermore, 1a was not toxic to normal human cells. Collectively, these data support that 1a represents a structural template for further development into potential cancer therapeutics with a novel mechanism of action.
- Li, Bingbing X.,Yamanaka, Kinrin,Xiao, Xiangshu
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supporting information
p. 6811 - 6820
(2013/01/15)
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- Synthesis and β-adrenergic blocking activity of naphthyloxypropylamines
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A series of 1-isopropylamino-3-(3′-substituted-2′-naphthyloxy)- 2-propanols have been synthesized and their structures have been confirmed by spectral analysis. All the derivatives have shown β-adrenergic blocking effect when tested on perfused frog heart. Compound 4e exhibited 100% blockade of adrenaline response.
- Vattipalli, Ramya,Shirodkar, Prabhakar Y.,Somani, Rakesh R.,Kadam, Vilasrao J.
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experimental part
p. 1587 - 1590
(2009/04/07)
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- Method for producing naphthalene carboxylic acid amide compound
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The present invention provides a method for producing a naphthalenecarboxylic acid amide compound represented by formula [1] comprising, reacting a naphthalenecarboxylic acid halide compound represented by formula [2] with ammonium acetate in a solvent having an ether bond. According to the method of the present invention, a naphthalene carboxylic acid amide compound can be obtained at high yield and at low cost.
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Page/Page column 9
(2008/06/13)
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- Catalytic enantioselective synthesis of flavanones and chromanones
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The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a β-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the β-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones. Copyright
- Biddle, Margaret M.,Lin, Michael,Scheidt, Karl A.
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p. 3830 - 3831
(2008/02/04)
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- Design and synthesis of highly potent and selective (2-arylcarbamoyl- phenoxy)-acetic acid inhibitors of aldose reductase for treatment of chronic diabetic complications
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Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective (2-arylcarbamoyl-phenoxy)-acetic acid aldose reductase inhibitors. The compound class features a core template that utilizes an intramolecular hydrogen bond to position the key structural elements of the pharmacophore in a conformation, which promotes a high binding affinity. The lead candidate, example 40, 5-fluoro-2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-phenoxyacetic acid, inhibits aldose reductase with an IC50 of 30 nM, while being 1100 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. In addition, example 40 lowers nerve sorbitol levels with an ED50 of 31 mg/kg/d po in the 4-day STZ-induced diabetic rat model.
- Van Zandt, Michael C.,Sibley, Evelyn O.,McCann, Erin E.,Combs, Kerry J.,Flam, Brenda,Sawicki, Diane R.,Sabetta, Al,Carrington, Anne,Sredy, Janet,Howard, Eduardo,Mitschler, Andre,Podjarny, Alberto D.
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p. 5661 - 5675
(2007/10/03)
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- Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives
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Chiral 1,5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship between the substitution of the naphthalene starting materials and reactivity/selectivity is determined by several factors which act in concert: (1) the effect of substituents on the oxidation potential of the substrate, (2) the ability of the substrate to participate in a chelated copper complex which depends on (a) the inherent coordinating ability of the 3-substituent and (b) substituent steric interactions that affect chelation between the 2-hydroxyl and 3-substituent, (3) the effect of substituents on dissociation of the product from the copper catalyst.
- Li, Xiaolin,Hewgley, J. Brian,Mulrooney, Carol A.,Yang, Jaemoon,Kozlowski, Marisa C.
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p. 5500 - 5511
(2007/10/03)
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- Secondary Benzylation Using Benzyl Alcohols Catalyzed by Lanthanoid, Scandium, and Hafnium Triflate
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The combination of a secondary benzyl alcohol and a metal triflate (e.g., La, Yb, Sc, and Hf triflate) in nitromethane was a highly effective secondary-benzylation system. Secondary benzylation of carbon (aromatic compounds, olefins, an enol acetate), nitrogen (amide derivatives), and oxygen (alcohols) nucleophiles was carried out with a secondary benzyl alcohol and 0.01-1 mol % of a metal triflate in the presence of water. Secondary benzyl alcohols and nucleophiles bearing acid-sensitive functional groups (e.g., tert-butyldimethylsilyloxy and acetoxy groups and methyl and benzyl esters) could be used for alkylation. Hf(OTf)4 was the most active catalyst for this alkylation, and trifluoromethanesulfonic acid (triflic acid, TfOH) was also a good catalyst. The catalytic activity of metal triflates and TfOH increased in the order La(OTf)3 3 3 4. A mechanistic study was also performed. The reaction of 1-phenylethanol (4a) in the presence of Sc(OTf) 3 in nitromethane gave an equilibrium mixture of 4a and bis(1-phenylethyl) ether (54). Addition of a carbon nucleophile to the equilibrium mixture gave alkylated product in high yield.
- Noji, Masahiro,Ohno, Tomoko,Fuji, Koji,Futaba, Noriko,Tajima, Hiroyuki,Ishii, Keitaro
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p. 9340 - 9347
(2007/10/03)
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- Stereognostic coordination chemistry. 1. The design and synthesis of chelators for the uranyl ion
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A new approach to the molecular recognition of metal oxo cations is introduced based on a ligand design strategy that provides at least one hydrogen bond donor for interaction with oxo group(s) as well as conventional electron pair donor ligands for coord
- Franczyk, Thaddeus S.,Czerwinski, Kenneth R.,Raymond, Kenneth N.
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p. 8138 - 8146
(2007/10/02)
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