- Efficient Pyrazolo[5,4-f]quinoxaline Functionalized Os(II) Based Emitter with an Electroluminescence Peak Maximum at 811 nm
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Upon fusing the pyrazinyl pyrazole entity in giving pyrazolo[3,4-f]quinoxaline chelate, the corresponding Os(II) based NIR emitter exhibited “invisible” and efficient electroluminescence with a peak maximum at 811 nm. A maximum external quantum efficiency
- Zhu, Ze-Lin,Wang, Sheng-Fu,Fu, Li-Wen,Tan, Ji-Hua,Cao, Chen,Yuan, Yi,Yiu, Shek-Man,Zhang, Ye-Xin,Chi, Yun,Lee, Chun-Sing
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- Electrochemical benzylic oxidation of C-H bonds
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Oxidized products have become increasingly valuable as building blocks for a wide variety of different processes and fine chemistry, especially in the benzylic position. We report herein a sustainable protocol for this transformation through C-H functionalization and is performed using electrochemistry as the main power source and tert-butyl hydroperoxide as the radical source for the C-H abstraction. The temperature conditions reported here do not increase above 50 °C and use an aqueous-based medium. A broad substrate scope is explored, along with bioactive molecules, to give comparable and increased product yields when compared to prior reported literature without the use of electrochemistry.
- Marko, Jason A.,Durgham, Anthony,Bretz, Stacey Lowery,Liu, Wei
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supporting information
p. 937 - 940
(2019/01/23)
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- Synthesis of a novel tricyclic 1,2,3,4,4a,5,6,10b-octahydro-1,10-phenanthroline ring system and CXCR4 antagonists with potent activity against HIV-1
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Stereorandom and diastereoselective syntheses of a novel 1,2,3,4,4a,5,6,10b-octahydro-1,10-phenanthroline ring system are described. Derivatives of all four diastereomers were prepared and isolated in >98% ee. The pure enantiomers were compared in order t
- Catalano, John G.,Gudmundsson, Kristjan S.,Svolto, Angilique,Boggs, Sharon D.,Miller, John F.,Spaltenstein, Andrew,Thomson, Michael,Wheelan, Pat,Minick, Doug J.,Phelps, Dean P.,Jenkinson, Stephen
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experimental part
p. 2186 - 2190
(2010/07/05)
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- Kilogram-scale synthesis of the CXCR4 antagonist GSK812397
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An improved, scalable synthesis of the CXCR4 antagonist GSK812397 is described. This new route was recently scaled up in 50 L fixed equipment to afford 1.2 kg of drug substance in five steps with an overall yield of 20% and >99% chemical and enantiomeric
- Boggs, Sharon,Elitzin, Vassil I.,Gudmundsson, Kristjan,Martin, Michael T.,Sharp, Matthew J.
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scheme or table
p. 781 - 785
(2010/04/22)
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- QUINOLYNYLMETHYLIMIDIZOLES AS THERAPEUTIC AGENTS
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Disclosed herein is a compound of the formula (I):(I).Therapeutic methods, compositions and medicaments related thereto are also disclosed.
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Page/Page column 14; 15
(2008/12/07)
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- 7-((1H-imidazol-4-yl)methyl)-5,6,7,8-tetrahydroquinoline
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A compound having a structure or a pharmaceutically acceptable salt, or a prodrug thereof is disclosed herein. Therapeutic methods, compositions, and medicaments related thereto are also disclosed.
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Page/Page column 7-8
(2008/06/13)
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- 8-PHENYL-5,6,7,8-HYDROQUINOLINE TACHYKININ RECEPTOR ANTAGONISTS
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The present invention is directed to certain 8-phenyl-5,6,7,8-hydroquinolinecompounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceut
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Page/Page column 22
(2008/06/13)
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- CYCLOALKANOPYRIDINE DERIVATIVE
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Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.
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Page/Page column 33
(2010/11/24)
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- CHEMCIAL COMPOUNDS
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The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind specifically to the chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 and/or CCR5 of a target cell.
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Page/Page column 39
(2010/10/20)
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- Chemokine receptor binding heterocyclic compounds with enhanced efficacy
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The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).
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- Convenient synthesis of 5,6,7,8-tetrahydroquinolin-8-ylamine and 6,7-dihydro-5H-quinolin-8-one
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A novel two-step synthesis of 5,6,7,8-tetrahydroquinolin-8-ylamine, involving regioselective nitrosation of 5,6,7,8-tetrahydroquinoline followed by oxime reduction, is described. Oxime hydrolysis affords 6,7-dihydro-5H-quinolin-8-one.
- McEachern,Yang,Chen,Skerlj,Bridger
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p. 3497 - 3502
(2007/10/03)
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- Chemokine receptor binding heterocyclic compounds with enhanced efficacy
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The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).
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Page/Page column 9
(2010/02/03)
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- Synthesis of enantiomerically pure amino-substituted fused bicyclic rings
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This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.
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- Superelectrophilic activation of 8-hydroxyquinoline in acid media and its reactions with weak nucleophiles
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According to the 1H and 13C NMR data, 5-azonia-4-hydroxynaphthalen-1-onium cation, generated by protonation of 8-hydroxyquinoline in the system CF3SO3H-SbF5, reacts with cyclohexane to give diprotonated 5,6,7,8-tetrahydroquinolin-8-one. Further reaction of the latter with cyclohexane yields 5,6,7,8-tetrahydroquinolinium ion. The reaction of 8-hydroxyquinoline with benzene in the presence of aluminum bromide or chloride gives 6-phenyl-5,6,7,8-tetrahydroquinolin-8-one and product of its intramolecular cyclization, 11-hydroxy-6,11-dihydro-6,11-methano-5H-benzo[5,6]cyclohepta[1,2-b]pyridine. The effect of the protonated nitrogen atom on the electrophilicity of dications is discussed.
- Koltunov,Repinskaya
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p. 437 - 442
(2007/10/03)
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- Synthesis of some unsymmetrical bridged terpyridines
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Novel unsymmetrical terpyridines 1 and 2 are synthesized using intra- and intermolecular Michael additions as the key reactions, followed by the construction of the central pyridine ring. Terpyridine 1 represents a heretofore unknown hexacyclic ring system.
- Kelly, T. Ross,Lebedev, Rimma L.
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p. 2197 - 2205
(2007/10/03)
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- Heterocyclic-fused lactams promote release of growth hormone
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There are disclosed certain novel compounds identified as heterocyclic-fused lactams which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible
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- Electrostatic acceleration of enolization in cationic ketones
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Rate constants for the water, acetate, and hydroxide ion-catalyzed enolizations of the cationic ketones 2-acetyl-1-methylpyridinium ion (3) and 1-methyl-8-oxo-5,6,7,8-tetrahydroquinolinium ion (4) have been measured at 25°C and compared with those reporte
- Tobin, John B.,Frey, Perry A.
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p. 12253 - 12260
(2007/10/03)
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- Vinyliminophosphorane-mediated preparation of 2-arylquinoline and 4-aryl-1-azaanthraquinone derivatives. X-Ray crystal structure of 1,2-dihydro-3H-indazolo[2,3-a]quinolin-4-one
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The reaction of the iminophosphorane derived from 3-azidocyclohexan-2-enone with substituted cinnamyl aldehydes affords 2-aryl-tetrahydroquinoline derivatives, which are easily converted into 2-arylquinolones. By contrast, iminophosphorane derived from 2-azidocyclohex-2-enone reacts only with α,β-unsaturated aldehydes without substituent at β-position to give 5,6-dihydro-8(7H)quinolinones. The iminophosphorane derived from 2-azido-1,4-naphthoquinone reacts with substituted cinnamyl aldehydes providing directly 4-aryl-1-azaanthraquinones. The crystal and molecular structure of 1,2-dihydro-3H-indazolo[2,3-a]quinolin-4-ono has been solved by X-Ray analysis.
- Molina,Molina, Pedro,Pastor,Pastor, Aurelia,Vilaplana,Vilaplana, Maria Jesus,Foces-Foces,Foces-Foces, Concepcion
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p. 1265 - 1276
(2007/10/02)
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- β-Amino Ketones as Key Intermediates in the Synthesis of Pyridines: A Novel and Efficient Route to Annelated Bi- and Terpyridines
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The hydrochlorides of β-amino ketones 1a-e (Mannich bases) are easily obtained starting compounds for a novel synthesis of pyridines.Condensation with the heteroaromatic ketones 8, 9, and 10 yields 5,6-dihydro-1,10-phenanthrolines 3a-d, 13 and 4,5-diazafluorenes 4a-d, which have not yet been described in literature.Symmetrical terpyridines 3e, 4e are formed in a one-step reaction of 8, 9 with dimethylmethylenammonium chloride in the presence of an ammonia source.
- Westerwelle, Ulrich,Esser, Achim,Risch, Nikolaus
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p. 571 - 576
(2007/10/02)
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- Twisted polyaza clefts for the complexation of cyclohexane-polyols
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A polyaza cleft was synthesized and shown to bind 1,2- and 1,3-cyclohexanediols and 1,3-2-cyclohexanetriol in chloroform.
- Huang,Cabell,Anslyn
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p. 7411 - 7414
(2007/10/02)
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- Applications of Organolithium and Related Reagents in Synthesis. Part 3. A General Study of the Reaction of Lithium Alkyls with Pyridine Ketones
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The reaction of MeLi and PhLi with acetylpyridines (1a-c) and their annelated derivatives (2a), (2b), (3), and (4) has been examined.The 3- and 4-pyridyl ketones (1b), (1c), (3), and (4) gave similar results to acetophenone and 3,4-dihydronaphthalen-1(2H)-one.In the case of the 2-pyridyl ketones (1a), (2a), and (2b) unexpectedly low yields of products resulted from the addition of RLi to the carbonyl group; the reaction was efficiently enhanced by initially adding an additional amount of LiBr.These results were accounted for by the chelation of RLi or LiBr by the 2-pyridyl ketones.
- Epsztajn, Jan,Bieniek, Adam
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p. 213 - 220
(2007/10/02)
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- Polyaza Cavity Shaped Molecules. Annelated Derivatives of 2-(2'-Pyridyl)-1,8-naphthyridine and 2,2'-Bi-1,8-naphthyridine
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A two-step method is presented for the oxidation of the 2-methylene position of 2,3-cycloalkenopyridines.The pyridyl ketones thus obtained may be reacted with 2-aminonicotinaldehyde to yield 3,3'-annelated derivatives of 2-(2'-pyridyl)-1,8-naphthyridine.T
- Thummel, Randolph P.,Lefoulon, Francois,Cantu, David,Mahadevan, Ramanathan
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p. 2208 - 2212
(2007/10/02)
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