- Aqueous highly emissive host-guest systems by host enhanced intramolecular charge transfer
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Highly emissive host-guest systems have been an emerging topic which combines dynamic supramolecular system with fluorescent dyes. In this work, we report the host-guest interactions between (E)-1-benzyl-4-(2-(pyren-1-yl)vinyl)pyridin-1-ium bromide (PVP)
- Si, Yaxin,Zhang, Qi,Jin, Weihang,Yang, Shun,Wang, Zhenwei,Qu, Dahui
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Read Online
- Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
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A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
- Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
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p. 4327 - 4337
(2021/05/31)
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- COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES
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The present invention provides a compound of formula (Ia) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, solid forms, combinations of pharmacologically active agents, pharmaceutical compositions and methods of using such compounds and solid forms thereof to treat or prevent parasitic diseases, for example malaria.
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Paragraph 0440-0442
(2021/04/23)
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- TRICYCLIC DEGRADERS OF IKAROS AND AIOLOS
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Tricyclic cereblon binders for the degradation of Ikaros or Aiolos by the ubiquitin proteasome pathway for therapeutic applications are described.
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Page/Page column 308-309
(2020/10/21)
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- CEREBLON BINDERS FOR THE DEGRADATION OF IKAROS
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The present invention provides cereblon binders for the degradation of Ikaros or Aiolos by the ubiquitin proteasome pathway along with their use in therapeutic applications as described herein.
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Page/Page column 381; 382
(2019/10/23)
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- N-benzyl-tetrahydropyridine compound and preparation method thereof
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The invention provides an N-benzyl-tetrahydropyridine compound and a preparation method thereof, and the preparation method comprises the following steps: S1, adding benzyl bromide into a pyridine compound to carry out nucleophilic substitution reaction t
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Paragraph 0051-0055
(2019/06/30)
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- Potent and Selective Tetrahydroisoquinoline Kappa Opioid Receptor Antagonists of Lead Compound (3 R)-7-Hydroxy- N-[(1 S)-2-methyl-1-(piperidin-1-ylmethyl)propyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (PDTic)
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Past studies have shown that it has been difficult to discover and develop potent and selective κ opioid receptor antagonists, particularly compounds having potential for clinical development. In this study, we present a structure-activity relationship (SAR) study of a recently discovered new class of tetrahydroisoquinoline κ opioid receptor antagonists which led to (3R)-7-hydroxy-N-{(1S)-2-methyl-1-[(-4-methylpiperidine-1-yl)methyl]propyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (12) (4-Me-PDTic). Compound 12 had a Ke = 0.37 nM in a [35S]GTPγS binding assay and was 645- and >8100-fold selective for the κ relative to the μ and δ opioid receptors, respectively. Calculated log BB and CNS (central nervous system) multiparameter optimization (MPO) and low molecular weight values all predict that 12 will penetrate the brain, and pharmacokinetic studies in rats show that 12 does indeed penetrate the brain.
- Ondachi, Pauline W.,Kormos, Chad M.,Runyon, Scott P.,Thomas, James B.,Mascarella, S. Wayne,Decker, Ann M.,Navarro, Hernán A.,Fennell, Timothy R.,Snyder, Rodney W.,Carroll, F. Ivy
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supporting information
p. 7525 - 7545
(2018/09/12)
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- Dynamic Covalent Chemistry of Nucleophilic Substitution Component Exchange of Quaternary Ammonium Salts
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Dynamic covalent libraries (DCLs) of quaternary ammonium cations were set up by reversible nucleophilic substitution (SN2′ and SN2) exchange reactions of ammonium salts and tertiary amines. The reactions were conducted at 60 °C to generate thermodynamically and kinetically controlled mixtures of quaternary ammonium compounds and tertiary amines, and were accelerated by using iodide as a nucleophilic catalyst. Microwave irradiation was used to assist the exchange reaction between the pyridinium salts and pyridine derivatives. Finally, experiments towards the generation of dynamic ionic liquids were performed. The results of this study pave the way for the extension of dynamic combinatorial chemistry to nucleophilic substitution reactions.
- Kulchat, Sirinan,Lehn, Jean-Marie
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p. 2484 - 2496
(2015/11/02)
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- Preparation of quaternary pyridinium salts as possible proton conductors
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On basis of earlier experimental experience, the transfer of protons in salts of the organic cation-inorganic anion type occurs primarily through directional arrangement of the anion-anion type short hydrogen bonds. The submitted work presents the prepara
- Urban, Ji,Havlek, David,Krajbich, Josef
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p. 448 - 455
(2015/02/19)
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- Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation
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Promoted by iodide anion the rhodium complex dimer, [Cp RhCl 2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6-tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH-Et 3N) mixture at 40 °C, with catalyst loadings as low as 0.005mol% being feasible. Copyright
- Wu, Jianjun,Tang, Weijun,Pettman, Alan,Xiao, Jianliang
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supporting information
p. 35 - 40
(2013/03/13)
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- The role of ion/neutral complexes in the fragmentation of N-benzyl-(alkylpyridinium) ions
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N-Benzylpyridinium ions bearing an alkyl group at the pyridine nucleus were studied as potential precursors of gaseous ion/neutral complexes. The occurrence of I/N complexes [C6H5CH2 + ? alkylpyridine] was probed by the reactivity of the potential benzylic hydride donor sites present in the ortho-, meta- and para-alkyl groups (R = methyl, ethyl, isopropyl and benzyl). Collision-induced dissociation of the ions, carried out in an electrical ion cage mass spectrometer, revealed that hydride transfer strongly depends both on the energy requirements of the hydride transfer but also on the position of the hydride donor. Hydride transfer, giving rise to the loss of toluene, was found to occur exclusively with those N-benzylpyridinium ions which bear an isopropyl or a benzyl substituent in the ortho position of the pyridine ring, thus reflecting the intermediacy of I/N complexes. All of the putative hydride donor alkyl groups were found to be non-reactive in the meta and para positions, as were methyl and ethyl groups even in the ortho positions. Density functional calculations (B3LYP/6-311+G/3d,2p)//(B3LYP/6-31+G(d)) on the hydride-transfer and simple-cleavage channels were carried out to help rationalizing these observations. The results suggest that the intra-complex hydride abstraction from the 3- and 4-isopropyl- and from the 3- and 4-benzylpyridine neutrals, although being thermodynamically favorable, is suppressed by substantial intra-complex rotational (or reorientation) barriers.
- Kuck, Dietmar,Grützmacher, Hans-Friedrich,Barth, Dieter,Heitkamp, Sandra,Letzel, Matthias C.
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body text
p. 159 - 166
(2012/07/13)
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- Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines
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A three-step method for the preparation of CF3-substituted 1,2,3,4-tetrahydroisoquino-lines and 1,2,3,6-tetrahydropyridines has been suggested. The first step includes alkylation of isoquinoline or 4-methylpyridine at the nitrogen atom with the
- Chernyshov, I. Yu.,Levin,Dilman,Belyakov,Struchkova,Tartakovsky
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experimental part
p. 2102 - 2107
(2011/06/26)
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- Reaction of N-alkylpyredinium salts with phosphorus trichloride
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1-Alkylpyridinium bromides 1 having activated N-methylene group react with phosphorus trichloride to give N-(dichlorophosphinomethylene)pyridinium ylides 2. The site of the reaction in 1,2-dialkylpyridinium halides 3 under these conditions is determined by the relative activation of 1- and 2-methylene groups; in the absence of sufficient activation of N-methylene group, reaction occurs at the 2-methylene group to give dichlorophosphinylated anhydrobases 5 and 11. 1,4-Dialkylpyridinium bromide 13 behaves analogously to give the corresponding dichlorophosphinylated anhydrobase 14.
- Bansal, Raj K.,Gupta, Neelima,Gupta, Rakhi,Pandey, Garima,Agarwal, Mamta
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p. 121 - 130
(2007/10/03)
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- 2-Cyano-Δ3-piperideines. 12. Stereochemistry of Formation of N-Benzyl-2-cyano-Δ3-piperideines and Facile Isomerization on Alumina to 2-Cyano-Δ4-piperideines. A Potentially General Route to the Synthesis of 2,6-Disubstitute
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The reaction of the piperideine N-oxides 1a-f with trifluoroacetic anhydride in CH2Cl2 at 0 deg C (Polonovski-Potier reaction) led to the formation of the N-benzyl-2-cyano-Δ3-piperideines 3a-f.Epimeric mixtures were obtained for the amino nitri
- Bonin, Martine,Romero, Jose Ricardo,Grierson, David S.,Husson, Henri-Philippe
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p. 2392 - 2400
(2007/10/02)
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