- Oligo(naphthylene-ethynylene) molecular rods
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Molecular rods designed for surface chirality studies have been synthesized in high yields. The molecules are composed of oligo(naphthylene-ethynylene) skeletons and functionalized at their two termini with carboxylic acids and hydrophobic groups. The molecular skeletons were constructed by means of palladium-catalyzed Sonogashira reactions between naphthyl halides and acetylenes. The triazene functionality was used as a protected iodine precursor to allow linear extension of the molecular rods during the syntheses. The carboxylic acid groups in the target molecules were protected as esters during the synthesis to keep the large aromatic molecules soluble during their syntheses. These rigid oligomers were designed to form lamella-like structures when adsorbed on a surface, through which multiple distinguishable surface conformations should be obtainable. Preliminary scanning tunneling microscopy imaging confirmed these properties. Copyright
- Cramer, Jacob R.,Ning, Yanxiao,Shen, Cai,Nuermaimaiti, Ajiguli,Besenbacher, Flemming,Linderoth, Trolle R.,Gothelf, Kurt V.
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- Discovery of novel, orally active dual NK1/NK2 antagonists
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Exploration of the SAR around selective NK2 antagonists, SR48968 and ZD7944, led to the discovery that naphth-1-amide analogues provide potent dual NK1 and NK2 antagonists. ZD6021 inhibited binding of [3H]-NKA or [3H]-SP to human NK1 and NK2 receptors, with high-affinity (Ki=0.12 and 0.62 nM, respectively). In functional assays ZD6021 had, at 10-7 M, in human pulmonary artery pKB=8.9 and in human bronchus pKB=7.3, for NK1 and NK2, respectively. Oral administration of ZD6021 to guinea pigs dose-dependently attenuated ASMSP induced extravasation of plasma proteins, ED50=0.5 mg/kg, and NK2 mediated bronchoconstriction, ED50=13 mg/kg.
- Bernstein, Peter R.,Aharony, David,Albert, Jeffrey S.,Andisik, Donald,Barthlow, Herbert G.,Bialecki, Russell,Davenport, Timothy,Dedinas, Robert F.,Dembofsky, Bruce T.,Koether, Gerard,Kosmider, Benedict J.,Kirkland, Karin,Ohnmacht, Cyrus J.,Potts, William,Rumsey, William L.,Shen, Lihong,Shenvi, Ashok,Sherwood, Scott,Stollman, David,Russell, Keith
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- A new 2D Cu-MOF constructed from carboxylate ligands containing C-H?π interactions as a recyclable responsive luminescent sensor for VOCs
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A new type of 2D metal-organic framework (MOF), namely Cu-MOF, was constructed from Cu(NO3)2·3H2O and the novel ligand 1,4-bis(4-naphthoic acid)benzene. The C-H?π interactions in the Cu-MOF effectively reduced aggregation-caused quenching (ACQ) due to restrictions in intramolecular motion (RIM), increased fluorescence, and controlled crystal packing properties, resulting in low dimensional parallelogram channels and a responsive “turn-on” fluorescence. The activated Cu-MOF exhibited excellent chemical sensing properties to various volatile organic compounds (VOCs) and showed excellent recyclability.
- Liu, Chengxin,Cui, Jin,Wang, Yufang,Zhang, Mingjie
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- Preparation method of 1,4-naphthalic acid
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The invention relates to a preparation method of 1,4-naphthalic acid, which is characterized by comprising the steps of performing Friedel-Crafts reaction on 1-naphthalene bromide serving as an initial raw material and acetyl chloride to generate 4-bromo-1-acetyl naphthalene; then carrying out oxidation by using pypocholoride to obtain 4-bromo-1-naphthoic acid; reacting 4-bromine-1-naphthoic acid with cuprous cyanide in a polar aprotic solvent in the presence of potassium iodide and copper sulfate in catalytic doses to generate a 4-cyano naphthoic acid copper salt complex; and carrying out alkaline hydrolysis on the 4-cyano naphthoic acid copper salt complex to obtain the 1,4-naphthalic acid. According to the preparation method of the naphthalene-1,4-dicarboxylic acid, the raw materials are easy to obtain, and the product does not contain color impurities, is high in purity and good in quality, and can be directly used as an intermediate of a dye, an ultraviolet light absorber, a scintillator and an optical whitening agent for further synthesis.
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Paragraph 0018-0019; 0022
(2021/05/12)
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- UiO-67-type Metal-Organic Frameworks with Enhanced Water Stability and Methane Adsorption Capacity
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The structure and properties of two new UiO-67-type metal-organic frameworks, along with their linker synthesis and powder and single crystal synthesis, are presented. The new MOFs, UiO-67-Me and UiO-67-BN, are based on 3,3′-dimethylbiphenyl and 1,1′-binaphthyl linker scaffolds, and show a much higher stability to water than the thoroughly investigated UiO-67, which is based on the biphenyl scaffold. On the basis of structure models obtained from single crystal X-ray diffraction, it is seen that these linkers are partly shielding the Zr cluster. The new materials have higher density than UiO-67, but show a higher volumetric adsorption capacity for methane. UiO-67-BN exhibits excellent reversible water sorption properties, and enhanced stability to aqueous solutions over a wide pH range; it is to the best of our knowledge the most stable Zr-MOF that is isostructural to UiO-67 in aqueous solutions.
- ?ien-?Degaard, Sigurd,Bouchevreau, Boris,Hylland, Knut,Wu, Lianpao,Blom, Richard,Grande, Carlos,Olsbye, Unni,Tilset, Mats,Lillerud, Karl P.
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supporting information
p. 1986 - 1991
(2016/03/19)
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- Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents
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To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl)indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl)indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity.
- Wiley, Jenny L.,Smith, Valerie J.,Chen, Jianhong,Martin, Billy R.,Huffman, John W.
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p. 2067 - 2081
(2012/06/01)
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- Development of the route of manufacture of an oral H1-H 3 antagonist
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A new route to an H1-H3 antagonist was developed to address scalability and environmental and cost of goods issues associated with the initial route.
- Harling, Sandra J.,Herbal, Karim,Langlade, Nathalie,Sanganee, Mahesh,Strachan, John B.,Turner, Peter G.,Whiting, Matthew P.,Bret, Guillaume,Loft, Mike,Negus, Alan,Shanahan, Steve
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experimental part
p. 112 - 122
(2011/10/13)
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- CYP17 inhibitors. Annulations of additional rings in methylene imidazole substituted biphenyls: Synthesis, biological evaluation and molecular modelling
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Twenty-one novel compounds originating from two classes of annulated biphenyls were synthesized as mimetics of the steroidal A- and C-rings and examined for their potency as inhibitors of human CYP17. Selected compounds were tested for inhibition of the hepatic CYP enzyme 3A4. Potent CYP17 inhibitors were found for each class, compound 9 (17 and 71% at 0.2 and 2 μM, respectively) and 21 (591 nM). Compound 21 showed only weak inhibition of CYP3A4 (32 and 64% at 2 and 10 μM, respectively). Both compounds, however, exhibited moderate to strong inhibition of the glucocorticoid-forming enzyme CYP11B1. The most interesting compounds were docked into our protein model. They bound into one of the modes which we have previously published. New interaction regions were identified.
- Pinto-Bazurco Mendieta, Mariano A. E.,Negri, Matthias,Hu, Qingzhong,Hille, Ulrike E.,Jagusch, Carsten,Jahn-Hoffmann, Kerstin,Mueller-Vieira, Ursula,Schmidt, Dirk,Lauterbach, Thomas,Hartmann, Rolf W.
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experimental part
p. 547 - 609
(2009/04/04)
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- 3- (4-{ [4-(4-{ [3-(3, 3-DIMETHYL-1-PIPERIDINYL) PROPYL] 0XY} PHENYL) -1-PIPERIDINYL] CARBONYL }-1-NAPHTHALENYL) PROPANOIC OR PROPENOIC ACID AS H1 AND H3 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY AND/OR ALLERGIC DISORDERS
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The present invention relates to a compound of formula (I), or a salt thereof wherein the naphthalene ring can be substituted in the 2, 3, 4, 5, 6, 7 or 8 position by R1, and R1 represents -CH2CH2COOH or -CH=C(CH3)COOH, and to processes for their preparation, to compositions containing them and to their use in the treatment of various diseases such as allergic rhinitis.
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Page/Page column 37; 39
(2008/06/13)
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- The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis
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The mercury-mediated decarboxylation (Pesci reaction) of several substituted naphthoic anhydrides has been investigated by microwave synthesis. A laboratory microwave reactor was found to be ideal for small-scale preparations of this slow reaction, reducing reaction times from typically four days to less than 1 h for the three-step process. The ionic reaction medium rapidly heated to high temperatures under microwave heating and could be efficiently maintained by low microwave power settings. Generation of stoichiometric CO2 was safely contained within the reaction tubes. A simplified reaction procedure has been developed. For substituted naphthoic anhydrides, 1H NMR analysis of the naphthoate ester derivatives indicated no change in the regioisomer ratio compared to previously reported thermal values.
- Moseley, Jonathan D.,Gilday, John P.
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p. 4690 - 4697
(2007/10/03)
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- Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: Effects of different thio-heterocyclic rings and aminoalkyl side chains
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Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA mor
- Li, Zhigang,Yang, Qing,Qian, Xuhong
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p. 8711 - 8717
(2007/10/03)
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- Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide
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(Chemical Equation Presented) Oxidation of alkyl and cycloalkyl arenes with tert-butyl hydroperoxide catalyzed by bismuth and picolinic acid in pyridine and acetic acid gave the corresponding benzylic ketones (48-99%). Alternatively, oxidation of methyl arenes gave the corresponding substituted benzole acids (50-95%). Preliminary mechanistic studies were consistent with a radical mechanism rather than a bismuth(III)-bismuth(V) cycle.
- Bonvin, Yannick,Callens, Emmanuel,Larrosa, Igor,Henderson, David A.,Oldham, James,Burton, Andrew J.,Barrett, Anthony G. M.
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p. 4549 - 4552
(2007/10/03)
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- AMINOETHANOL DERIVATIVES
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The present invention provides a pharmaceutical agent having cholesteryl ester transfer protein inhibitory action and useful as a blood lipid lowering agent and the like. The present invention relates to a compound represented by the formula wherein Ar1 is an aromatic ring group optionally having substituents, Ar2 is an aromatic ring group having substituents, OR'' is an optionally protected hydroxyl group, R is an acyl group, R' is a hydrogen atom or a hydrocarbon group optionally having substituents, or a salt thereof, and a pharmaceutical composition containing a compound of the formula (I) or a salt thereof or a prodrug thereof.
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Page/Page column 55-56
(2010/11/30)
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- SYNTHESIS AND POLYMERIZATION OF SOME ETHYNYL TRIFLUOROMETHYL NAPHTHALENES
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Some bromonaphthoic acids were fluorinated with SF4 to bromo(trifluoromethyl)naphthalenes.Although a reaction of Grignard reagent of one of the bromides with Cl2C=CF2 gave low yield of a (dichlorofluorovinyl)(trifluoromethyl)naphthalene, lithio derivatives gave the desired ethynyl(trifluoromethyl)naphthalenes in improved yields after subsequent eliminations of the vinylic halogens with n-butyllithium.Polymerization of the acetylenes was carried out with photo-activated W(CO)6 catalyst to yield high-molecular-weight polymers.
- Okano, T.,Ito, K.,Kodaira, K.,Hosokawa, K.,Nishida, M.,et al.
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p. 139 - 152
(2007/10/02)
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- Preparation of a series of substituted fluoromethylnaphthalenes
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A series of 22 3- and 4-substituted 1-fluoromethylnaphthalenes have been synthesized.Details of practical procedures for the preparation of all intermediates are described, and physical properties for all of the substituted naphthalenes synthesized, and spectral parameters for 51 previously unknown compounds, are given.
- Dixon, Elisabeth A.,Fischer, Alfred,Robinson, Frank P.
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p. 2629 - 2641
(2007/10/02)
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- Kinetics of Base-catalysed Iodination of Substituted Acetonaphthones
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Kinetics of iodination of 6-substituted 2-acetonaphthones and of 4-substituted 1-acetonaphthones in 20percent pyridine-20percent methanol-60percent water (v/v) have been followed at three temperatures.The Hammett equation applies very well to these reactions.The rate constants for various heterocyclic base-catalysed iodination of acetophenone and of 1- and 2-acetonaphthones in 60percent (v/v) methanol-water solvent have been correlated with pKa values of the conjugate acids of the heterocyclic bases via the Broensted equation giving β values of 0.88, 1.01 and 0.92 for acetophenone, 1-acetonaphthone and 2-acetonaphthone respectively.The influence of solvent on the rates of pyridine-catalysed iodination of acetophenone and of 1- and 2-acetonaphthones has also been studied.
- Ananthakrishnanadar, P.,Gnanasekaran, C.
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p. 646 - 649
(2007/10/02)
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