16650-55-8Relevant academic research and scientific papers
Oligo(naphthylene-ethynylene) molecular rods
Cramer, Jacob R.,Ning, Yanxiao,Shen, Cai,Nuermaimaiti, Ajiguli,Besenbacher, Flemming,Linderoth, Trolle R.,Gothelf, Kurt V.
, p. 2813 - 2822 (2013)
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
Discovery of novel, orally active dual NK1/NK2 antagonists
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
, p. 2769 - 2773 (2001)
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.
A new 2D Cu-MOF constructed from carboxylate ligands containing C-H?π interactions as a recyclable responsive luminescent sensor for VOCs
Liu, Chengxin,Cui, Jin,Wang, Yufang,Zhang, Mingjie
, p. 4124 - 4128 (2021)
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.
Preparation method of 1,4-naphthalic acid
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Paragraph 0018-0019; 0022, (2021/05/12)
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.
UiO-67-type Metal-Organic Frameworks with Enhanced Water Stability and Methane Adsorption Capacity
?ien-?Degaard, Sigurd,Bouchevreau, Boris,Hylland, Knut,Wu, Lianpao,Blom, Richard,Grande, Carlos,Olsbye, Unni,Tilset, Mats,Lillerud, Karl P.
, p. 1986 - 1991 (2016/03/19)
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.
Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents
Wiley, Jenny L.,Smith, Valerie J.,Chen, Jianhong,Martin, Billy R.,Huffman, John W.
, p. 2067 - 2081 (2012/06/01)
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.
Development of the route of manufacture of an oral H1-H 3 antagonist
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
experimental part, p. 112 - 122 (2011/10/13)
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.
CYP17 inhibitors. Annulations of additional rings in methylene imidazole substituted biphenyls: Synthesis, biological evaluation and molecular modelling
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.
experimental part, p. 547 - 609 (2009/04/04)
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.
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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Page/Page column 37; 39, (2008/06/13)
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.
The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis
Moseley, Jonathan D.,Gilday, John P.
, p. 4690 - 4697 (2007/10/03)
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.
