- 18O-Isotope Effect in 13C Nuclear Magnetic Resonance Spectroscopy. 5 - Substituent Group Electronic Effects in Substituted Acetophenones
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A series of para- and meta-substituted acetophenones were prpared which were highly labeled with 18O at the carbonyl function.The natural abundance 13C NMR spectra of the compounds were recorded and the 18O-isotope-induced shifts of the carbonyl carbon we
- Risley, John M.,DeFrees, Shawn A.,Etten, Robert L. Van
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- INHIBITORS OF SPINSTER HOMOLOG 2 (SPNS2) FOR USE IN THERAPY
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The present disclosure provides SPNS2 inhibitor compounds according to Formula I and their pharmaceutically acceptable salts, and/or tautomers as described in the disclosure, and the disclosure provides their pharmaceutical compositions and methods of use
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Paragraph 00591; 00592-00593; 00608-00609
(2020/08/13)
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- NOVEL OXADIAZOLE COMPOUNDS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI
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The present invention discloses a compound of formula (I), Formula (I) wherein, R1, L1,A, L2, W1, R2f, R3f, Q, and R10 are as defined in the detailed description. The present invention also relates to a process for preparing the compound of formula (I).
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Page/Page column 62
(2020/10/21)
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- Selective targeting of dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin (Dc-Sign) with mannose-based glycomimetics: Synthesis and interaction studies of bis(benzylamide) derivatives of a pseudomannobioside
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Dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin (DC-SIGN) and Langerin are C-type lectins of dendritic cells (DCs) that share a specificity for mannose and are involved in pathogen recognition. HIV is known to use DC-SIGN on DCs to facilitate transinfection of T-cells. Langerin, on the contrary, contributes to virus elimination; therefore, the inhibition of this latter receptor is undesired. Glycomimetic molecules targeting DC-SIGN have been reported as promising agents for the inhibition of viral infections and for the modulation of immune responses mediated by DC-SIGN. We show here for the first time that glycomimetics based on a mannose anchor can be tuned to selectively inhibit DC-SIGN over Langerin. Based on structural and binding studies of a mannobioside mimic previously described by us (2), a focused library of derivatives was designed. The optimized synthesis gave fast and efficient access to a group of bis(amides), decorated with an azide-terminated tether allowing further conjugation. SPR inhibition tests showed improvements over the parent pseudomannobioside by a factor of 3-4. A dimeric, macrocyclic structure (11) was also serendipitously obtained, which afforded a 30-fold gain over the starting compound (2). The same ligands were tested against Langerin and found to exhibit high selectivity towards DC-SIGN. Structural studies using saturation transfer difference NMR spectroscopy (STD-NMR) were performed to analyze the binding mode of one representative library member with DC-SIGN. Despite the overlap of some signals, it was established that the new ligand interacts with the protein in the same fashion as the parent pseudodisaccharide. The two aromatic amide moieties showed relatively high saturation in the STD spectrum, which suggests that the improved potency of the bis(amides) over the parent dimethyl ester can be attributed to lipophilic interactions between the aromatic groups of the ligand and the binding site of DC-SIGN. Receptor targeting: For the first time glycomimetics based on a mannose anchor have been tuned to selectively inhibit DC-SIGN (dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin) over Langerin. Based on structural and binding studies of a mannobioside mimic previously described, a focused library of derivatives was designed (see figure). Copyright
- Varga, Norbert,Sutkeviciute, Ieva,Guzzi, Cinzia,McGeagh, John,Petit-Haertlein, Isabelle,Gugliotta, Serena,Weiser, J?rg,Angulo, Jesús,Fieschi, Franck,Bernardi, Anna
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supporting information
p. 4786 - 4797
(2013/05/21)
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- CYCLOBUTYL CARBOXYLIC ACID DERIVATIVES
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The invention relates to compounds of formula (I) and to pharmaceutically acceptable salts, prodrugs, solvates or hydrates thereof. This invention also relates to a method of using such compounds in the treatment of hyperproliferative diseases and autoimm
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Page/Page column 52-53
(2009/06/27)
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- Light-driven charge separation in isoxazolidine-perylene bisimide dyads
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A series of arrays for lightdriven charge separation is presented, in which perylene tetracarboxylic bisimide is the light-absorbing chromophore and electron acceptor, whereas isoxazolidines are colourless electron donors, the electron-releasing propertie
- Langhals, Heinz,Obermeier, Andreas,Floredo, Yvonne,Zanelli, Alberto,Flamigni, Lucia
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experimental part
p. 12733 - 12744
(2010/06/19)
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- Direct synthesis of protected arylacetaldehydes by tetrakis(phosphane)- palladium-catalyzed arylation of ethyleneglycol vinyl ether
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A range of aryl bromides undergo Heck reaction with ethylene glycol vinyl ether, in the presence of [PdCl(C3H5)]2/ cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphanyl)methyl]cyclopentane as catalyst, to give regioselectively protected arylacetaldehydes in good yields. The β-arylation products were obtained in with 93-100 % selectivity with electron-poor aryl bromides or heteroaryl bromides. Furthermore, this catalyst can be used at low loading, even for reactions with sterically hindered aryl bromides. The aryl vinyl ether intermediates undergo subsequent ketalisation to give the corresponding 2-benzyl-1,3-dioxolane derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 765 - 774
(2007/10/03)
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- N-ALKYL PYRROLES AS HMG-COA REDUCTASE INHIBITORS
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HMGCo-A reductase inhibitor compounds useful as hypocholesterolemic and hypolipidemic compounds are provided. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided. Formula (I).
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Page/Page column 153
(2010/02/12)
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- AMIDE COMPOUND AND METHOD OF CONTROLLING PLANT DISEASE WITH THE SAME
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A amid compound of the formula (1): wherein, in the formula, R51 represents a halogen atom, a C1-C6 alkyl group and the like; R52 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group and the like; R53 represents a halogen atom and the like; R56 represents a halogen atom and the like; R57 represents a hydrogen atom and the like; R58 and R59 independently represent a hydrogen atom, a C1-C3 alkyl group and the like; R60 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, or a C3-C6 alkynyl group; R61 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group or a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group; R62, R63 and R64 represent a hydrogen atom, a halogen atom and the like; X represents a oxygen atom or a sulfur atom; has an excellent activity against plant diseases.
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Page/Page column 109-110
(2010/02/14)
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- Direct synthesis of protected arylacetaldehydes by palladium- tetraphosphine-catalyzed arylation of ethyleneglycol vinylether
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Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane as a catalyst, a range of aryl bromides undergo Heck reaction with ethyleneglycol vinylether to give regioselectively protected arylacetaldehydes in good yields. The β-arylation products were obtained in the range 93-98% selectivity with electron-poor aryl bromides. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides. The arylvinyl ethers intermediates undergo subsequent ketalization to give the corresponding 2-benzyl-1,3-dioxolane derivatives.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 1561 - 1564
(2007/10/03)
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- 1,3-Dioxolanes from carbonyl compounds over zeolite HSZ-360 as a reusable, heterogeneous catalyst
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Carbonyl compounds are converted, in good yields, into their 1,3-dioxolanes over zeolite HSZ-360, as a new reusable catalyst. Good chemoselectivity is also observed.
- Ballini, Roberto,Bosica, Giovanna,Frullanti, Bettina,Maggi, Raimondo,Sartori, Giovanni,Schroer, Frank
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p. 1615 - 1618
(2007/10/03)
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- Deactivation of Triplet Phenyl Alkyl Ketones by Conjugatively Electron-Withdrawing Substituents
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Para-cyano, -carbomethoxy, and -acyl substituents decrease the triplet reactivity of valerophenone (γ-hydrogen abstraction), whereas comparable meta substituents increase reactivity.Spectroscopic results are presented which indicate that para-(-R) substituents lower ?,?* triplet energies so much more than n,?* energies that the lowest triplets become largely ?,?* in nature.Meta-(-R) substituents do not stabilize ?,?* triplets enough to invert triplet levels.Both substitution patterns support a largely 1,4-biradical structure for the lowest ?,?* triplet of acylbenzenes.Ortho substituents show the usual steric anomalies: ortho cyano enhances valerophenone triplet reactivity by stabilizing the n,?* triplet; ortho carbomethoxy deactivates valerophenone by stabilizing the ?,?* triplet but not the n,?.*
- Wagner, Peter J.,Siebert, Elizabeth J.
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p. 7329 - 7335
(2007/10/02)
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