- Regioselective Single Electron Transfer Photocatalytic Synthesis of 2-Cyano-3-Ethylidenepiperidines. New Route to the Total Synthesis of (+/-) cis-Eburnamonine
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A new synthesis of (+/-) cis-eburnamonine is described through a tetracyclic intermediate 3 obtained from 2-cyano-3-ethylidenepiperidines generated in situ by a regioselective single electron transfer (SET) photocatalysis.
- Goes, Alexandre Da Silva,Ferroud, Clotilde,Santamaria, Jean
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- Hydroarylation of Arenes via Reductive Radical-Polar Crossover
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A photocatalytic system for the dearomative hydroarylation of benzene derivatives has been developed. Using a combination of an organic photoredox catalyst and an amine reductant, this process operates through a reductive radical-polar crossover mechanism where aryl halide reduction triggers a regioselective radical cyclization event, followed by anion formation and quenching to produce a range of complex spirocyclic cyclohexadienes. This light-driven protocol functions at room temperature in a green solvent system (aq. MeCN) without the need for precious metal-based catalysts or reagents or the generation of stoichiometric metal byproducts.
- Flynn, Autumn R.,Mcdaniel, Kelly A.,Hughes, Meredith E.,Vogt, David B.,Jui, Nathan T.
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supporting information
p. 9163 - 9168
(2020/07/10)
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- Novel protein kinase inhibitors related to tau pathology modulate tau protein-self interaction using a luciferase complementation assay
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The current number of drugs available for the treatment of Alzheimer's disease (AD) is strongly limited and their benefit for therapy is given only in the early state of the disease. An effective therapy should affect those processes which mainly contribu
- Holzer, Max,Schade, Nico,Opitz, Ansgar,Hilbrich, Isabel,Stieler, Jens,Vogel, Tim,Neukel, Valentina,Oberstadt, Moritz,Totzke, Frank,Schchtele, Christoph,Sippl, Wolfgang,Hilgeroth, Andreas
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- Ruthenium-Catalyzed Regioselective 1,4-Hydroboration of Pyridines
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Simple ruthenium precursor [Ru(p-cymene)Cl2]2 1 catalyzed regioselective 1,4-dearomatization of pyridine derivatives using pinacolborane is reported. Two catalytic intermediates, [Ru(p-cymene)Cl2Py] 2 and [Ru(p-cymene)Cls
- Kaithal, Akash,Chatterjee, Basujit,Gunanathan, Chidambaram
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supporting information
p. 3402 - 3405
(2016/07/26)
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- First biological evaluation of developed 3-benzyloxyfluorenes as novel class of MDR modulators
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A series of 3-benzyloxy-1-aza-9-oxafluorenes has been synthesized and biologically evaluated as novel MDR modulators. The concentration dependent inhibition of the efflux pump ABCB1 (P-glycoprotein) has been characterized and is discussed in relation to calculated lipophilicity data. Instead of the molecular lipophilicity the exact positioning of functional groups was found decisive for the biological activities.
- Krug, Martin,Voigt, Burkhardt,Baumert, Christiane,Lüpken, Ralf,Molnár, Joséf,Hilgeroth, Andreas
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experimental part
p. 2683 - 2688
(2010/07/09)
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- A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants
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(Chemical Equation Presented) A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.
- Nara, Susheel J.,Jha, Mukund,Brinkhorst, Johan,Zemanek, Tony J.,Pratt, Derek A.
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experimental part
p. 9326 - 9333
(2009/04/06)
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- HETEROBICYCLIC CARBOXAMIDES AS INHIBITORS FOR KINASES
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The invention relates to novel organic compounds of formula (I) and their use in the treatment of the animal or human body, to pharmaceutical compositions comprising a compound of formula (I) and to the use of a compound of formula (I) for the preparation of pharmaceutical compositions for use in the treatment of protein kinase dependent diseases, especially of proliferative diseases, such as in particular tumour diseases.
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Page/Page column 68
(2008/06/13)
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- BICYCLIC COMPOUNDS
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The present invention is to provide a bicyclic compound represented by the following formula: wherein Ring Q is pyridine or pyrimidine; Ring A is benzene or a heterocyclic ring; G is Ring B optionally having a substituent(s) R3, or an amino optionally substituted by one or two selected from the group consisting of alkyl(s), aralkyl(s) and cycloalkyl(s); Ring B is benzene, a heterocyclic ring, a cycloalkane or a cycloalkene; R1 is a group selected from the following formulae: R2 and R3 may be the same or different from each other, and each is cyano, nitro, etc.; m is 0, 1 or 2; R4 is hydrogen, a halogen, etc.; and R5 and R6 may be the same or different from each other, and each is hydrogen, an optionally substituted alkyl, etc., or a pharmaceutically acceptable salt thereof, which is a large conductance calcium-activated K channel opener useful for treatment of pollakiuria, urinary incontinence, etc.
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Page/Page column 47-48
(2010/02/14)
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- 3-`(HETERO) ARYLMETHOXY ! PYRIDINES AND THEIR ANALOGUES AS P38 MAP KINASE INHIBITORS
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Compounds of the formula (I), wherein: -X=Y- is selected from -CR2=CR3- and -CR2=N-; R1 is selected from H, halo, NRR', NHC(=O)R, NHC(=O)NRR', NH2SO2R, and C(=O)NRR'; R2 and R3 (where present) are independently selected from H, optionally substituted C1-7 alkyl, optionally substituted C5-20 aryl, optionally substituted C3-20 heterocyclyl, halo, amino, amido, hydroxy, ether, thio, thioether, acylamido, ureido and sulfonamino; R4 is an optionally substituted C5-20 aryl or C5-20 heteroaryl group; and R5 is selected from R5’, halo, NHR5’, C(=O)NHR5’, OR5’, SR5’, NHC(=O)R5’, NHC(=O)NHR5’, NHS(=O)R5’, wherein R5’ is H or C1-3 alkyl (optionally substituted by halo, NH2, OH, SH) are disclosed for use in therapy and for treating diseases ameliorated by inhibiting p38 MAP kinase.
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Page/Page column 63-64; 66
(2010/11/30)
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- Synthesis of substituted pyridines by the reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under focused microwave irradiation
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The nucleophilic substitution reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under microwave irradiation was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to those conducted under conventional heating processes.
- Cherng, Yie-Jia
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p. 4931 - 4935
(2007/10/03)
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- Synthesis of alkyl heteryl ethers from acetates under interphase catalysis conditions in a liquid/solid system
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The reaction of acetates of heterocyclic alcohols with alkyl halides in the two-phase catalytic system of solid KOH/C6H6/18-crown-6 at room temperature leads selectively to the formation of the corresponding heterocyclic ethers in 32-93% yield. 1998 Plenum Publishing Corporation.
- Abele,Abele,Gaukhman,Lukevics
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- Dipolar cycloaddition route to diverse analogues of cocaine: The 6- and 7-substituted 3-phenyltropanes
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In our quest for an antagonist or partial agonist of cocaine, access to certain 6- and 7-substituted 3-phenyltropanes of type I was required. Starting from 3-hydroxy-1-methyl-4-phenylpyridinium iodide, we disclose a pyridinium betaine-based dipolar cycloaddition route to tropenones of type II. In turn, we show how this intermediate can be transformed to type I products either through the copper-catalyzed conjugate addition reaction of Grignard reagents to the enones 7-9 or by the copper(I)-catalyzed cross coupling reaction of the allylic acetates 15a and 16a with Grignard reagents.
- Kozikowski, Alan P.,Araldi, Gian Luca,Ball, Richard G.
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p. 503 - 509
(2007/10/03)
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- Synthesis of 1-isopropylamino-3-(pyrazolo[1,5-a]-pyridyloxy)-2-propanols
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Treatment of the 4-hydroxypyrazolo[1,5-a]pyridine with glycidyl tosylate in the presence of base, followed by reaction with isopropylamine gave 1-isopropylamino-3-(pyrazolo[1,5-a]pyrid-4-yloxy)-2-propanol. In a similar manner, 1-isopropylamino-3-(pyrazolo[1,5-a]pyrid-6- and 1-isopropylamino-3-(pyrazolo[1,5-a]pyrid-3-yloxy)-2-propanol were also prepared.
- Miki, Yasuyoshi,Tasaka, Junko,Uemura, Kyoko,Miyazeki, Kunihiro,Yamada, Jun
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p. 2249 - 2256
(2007/10/03)
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- Pyrazolo[1,5-a]pyridine compounds, and production and use thereof
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A novel anti-serotonergic compound and the synthetic intermediates thereof are provided. The compound and intermediates are pyrazolo[1,5-a]pyridine compounds represented by the formula, STR1 wherein R1 represents --OH, --OCH2 -Ph (where Ph is a phenyl group), STR2 or --O--CH2 --CH(OH)--CH2 --NH--CH(CH3)2 ; and R2 is H or --COOR (wherein R is a C1 -C3 alkyl group). Among the compounds of the above formula, a compound wherein R1 is --O--CH2 --CH(OH)--CH2 --NH--CH(CH3)2 has anti-serotonergic activity and can be synthesized, for example, by way of compounds wherein R1 is OCH2 Ph and R2 is COOR, R1 is --OH and R2 is H, and R1 is STR3 and R2 is H, in order.
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- Synthesis of 4-Alkyl-3-pyridinols from 3-Benzyloxypyridine
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The addition of Grignard reagents to the 1-phenoxycarbonyl salt of 3-benzyloxypyridine and a catalytic amount of cuprous iodide afforded 4-alkyl-3-benzyloxy-1-phenoxycarbonyl-1,4-dihydropyridines in good yield.The crude dihydropyridines were aromatized wi
- Comins, Daniel L.,Stroud, Eric D.
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p. 1419 - 1420
(2007/10/02)
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- Kinetics of Benzylation of Hydroxypyridines & Hydroxyquinolines in Dimethyl Sulphoxide - Water & Isopropanol - Water Mixtures
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The kinetics of benzylation of hydroxypyridines and hydroxyquinolines have been investigated in DMSO-water and isopropanol-water mixtures.A formal comparison of rate of benzylation of phenols and naphthols has also been made.DMSO, being a dipolar aprotic solvent facilitates O-alkylation of phenols and naphthols and a considerable rate increase has been observed in DMSO-water, giving the O-alkylated products in more than 90percent yield in both the cases.However, in the case of benzylation of hydroxypyridine in DMSO-water, O-alkylated product formed is only 65percent and the magnitude of rate increase, compared to phenols and naphthols, is much less, under similar conditions.But the rate of benzylation of 8-hydroxyquinoline in DMSO-water is retarded considerably and the rate is even slower than the rate of N-benzylation of quinoline, indicating only O-benzylation of 8-hydroxyquinoline in DMSO-water is unique and is mainly due to greater ground state solvation of substrate by DMSO, a factor which has been considered insignificant in all the other cases.
- Rajasekar, N.,Srinivasan, V. S.,Venkatasubramanian, N.
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p. 800 - 802
(2007/10/02)
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