- Helix formation in synthetic polymers by hydrogen bonding with native saccharides in protic media
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Water-soluble poly(m-ethynylpyridine)s were designed to realize saccharide recognition in protic media. UV/Vis, 1HNMR, and fluorescence measurements revealed that the polymer forms a helical higher order structure by solvophobic interactions between the ethynylpyridine units in the protic medium. The resulting pore in the helix behaves like a binding pocket in proteins, by taking advantage of inwardly directed hydrogen-bonding functional groups of the polymers. Molecular recognition of native saccharides by the polymers was investigated by circular dichroism (CD). The chirality of the saccharide was transferred to the helical sense of the polymers, accompanied by the appearance of induced CDs (ICDs) in the absorptive region of the polymers. In MeOH/water (10/1), mannose and allose showed intense ICDs, and the apparent association constant between the polymer and D-mannose was 14M-1.
- Waki, Minoru,Abe, Hajime,Inouye, Masahiko
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- Highly Active Ruthenium CNC Pincer Photocatalysts for Visible-Light-Driven Carbon Dioxide Reduction
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Five ruthenium catalysts described herein facilitate self-sensitized carbon dioxide reduction to form carbon monoxide with a ruthenium catalytic center. These catalysts include four new and one previously reported CNC pincer complexes featuring a pyridino
- Das, Sanjit,Rodrigues, Roberta R.,Lamb, Robert W.,Qu, Fengrui,Reinheimer, Eric,Boudreaux, Chance M.,Webster, Charles Edwin,Delcamp, Jared H.,Papish, Elizabeth T.
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- Enantiopure substituted pyridines as promising antimalarial drug candidates
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We describe the enantioselective synthesis and biological evaluation of 4-(2-amino-1-hydroxyethyl)pyridines (4 AHPs) as new antimalarial drug candidates. In particular, two routes to obtain the key-intermediate 4-vinyl-pyridine were studied. These routes are based on a Kr?hnke-type cyclization or on metal-catalyzed reactions. The Kr?hnke-type cyclization route is faster but only efficient at low scale since this pathway involves a Wittig reaction that requires severe temperature-control. Consequently, we designed a second route based on metal-catalyzed reactions. This way is longer but the 4-vinyl-pyridine can be obtained on a 5 g scale at least. Finally, a regioselective SN2 ring-opening of enantiopure epoxides by alkyl primary amines allowed the synthesis of eight 4-AHPs with global yields up to 41%. These compounds show strong in vitro antimalarial activity against P. falciparum strains and are more active that chloroquine and mefloquine. These results demonstrate that 4-AHPs are promising antimalarial drug candidates.
- Agnamey, Patrice,Bentzinger, Guillaume,Dassonville-Klimpt, Alexandra,Guillon, Jean,Marchivie, Mathieu,Pair, Etienne,Sonnet, Pascal,Mullié, Catherine
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- NOVEL AMINOPYRIDINEMETHANOL COMPOUNDS AND THEIR USE
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The present invention is directed to novel compounds of Formula (I): pharmaceutically acceptable salts or solvates thereof, and their use, in particular in the treatment or prevention of malaria.
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Page/Page column 39; 59; 60
(2019/05/22)
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- Rate enhancement of hexose sugar oxidation on an ethynylpyridine- functionalized Pt/Al2O3 catalyst with induced chirality
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Rate enhancement of the selective oxidation of hexoses was achieved on an ethynylpyridine (EPy)-functionalized Pt/Al2O3 catalyst. Host-guest interaction between the EPy ligand and a hexose sugar reactant produced a complex with induced chirality on the catalyst surface.
- Waki, Minoru,Muratsugu, Satoshi,Tada, Mizuki
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supporting information
p. 7283 - 7285
(2013/09/23)
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- Integrating replication processes with mechanically interlocked molecular architectures
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A kinetic model for the integration of self-replication with the formation of a mechanically interlocked molecular architecture, namely a rotaxane, is presented. The logical steps required to convert this model into molecular structures through consideration of the design criteria highlighted by the model are discussed and executed. Ultimately, despite careful design, the rotaxane synthesised did not replicate as expected. The reasons for this failure are traced by experiment and computation to the sub-optimal association constant for the pseudorotaxane complex required to form the replicating rotaxane. Additionally, a deleterious supramolecular steric effect, operating through the proximity of the macrocyclic component of the pseudorotaxane to the transition state for the stoppering reaction is identified computationally.
- Vidonne, Annick,Philp, Douglas
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p. 8464 - 8475
(2008/12/22)
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- Remarkably strong, uncharged hydrogen-bonding interactions of polypyridine-macrocyclic receptors for deoxyribofuranosides
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Novel macrocyclic saccharide receptors that possess a pyridine-pyridone- pyridine arrangement as a hydrogen-bonding motif are presented. The artificial receptors exhibited a remarkably strong binding affinity for deoxyribofuranoside derivatives in CDClsu
- Inouye, Masahiko,Takahashi, Kunihide,Nakazumi, Hiroyuki
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p. 341 - 345
(2007/10/03)
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