- Novel carbocationic rearrangements of 1-styrylpropargyl alcohols
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The dehydration and subsequent cyclization reactions of 1-styrylpropargyl alcohols was examined. In the course of these studies, numerous scaffolds were synthesized, including a furan, a cyclopentenone, an acyclic enone and even a naphthalenone. The diversity of these structural motifs lies in novel cascades of reactions originating from a common carbocationic manifold.
- Basmadjian, Christine,Zhang, Fan,Dsaubry, Laurent
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supporting information
p. 1017 - 1022
(2015/08/18)
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- GUANIDINE DERIVATIVES AS TRPC MODULATORS
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The present invention is directed to guanidine derivatives as inhibitors of transient receptor potential canonical channels (TRPC channels), in particular TRPC3 and/or TRPC6 and/or TRPC7 activity, more particularly TRPC6 activity. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders mediated by TRPC channels (Formula (I))
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Page/Page column 42-43
(2014/02/16)
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- When inhibitors do not inhibit: Critical evaluation of rational drug design targeting chorismate mutase from mycobacterium tuberculosis
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Tuberculosis (TB) is a devastating disease that claims millions of lives every year. Hindered access or non-compliance to medication, especially in developing countries, led to drug resistance, further aggravating the situation. With current standard ther
- Munack, Steffi,Leroux, Vincent,Roderer, Kathrin,?kvist, Mats,Van Eerde, André,Gundersen, Lise-Lotte,Krengel, Ute,Kast, Peter
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p. 2507 - 2527
(2013/01/16)
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- Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination
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The effect of the chlorine position on the C-Cl bond hydrogenolysis and the enantioselective hydrogenation of Cl substituted (E)-2,3-diphenylpropenoic acid derivatives has been studied over cinchonidine-modified Pd/Al2O 3. In contrast to the fast hydrodechlorination of the β-phenyl-para-Cl substituted acids the Cl on the α-phenyl ring was barely hydrogenolized. These observations were interpreted by the different arrangements of the two phenyl rings on the surface, with the α- and β-phenyl rings adsorbed tilted and parallel, respectively. The results confirmed the beneficial effect of the α-phenyl-ortho-substituents on the chiral discrimination, thus the 2,3-diphenylpropionic acids substituted by Cl on the α-phenyl ring could be prepared in good yields and optical purities. The conclusions were used for the rational design of an acid, i.e. (E)-2-(2-methoxyphenyl)-3-(3,4-difluorophenyl)propenoic acid, which afforded the best optical purity (ee up to 95% at 295 K) described until now in this heterogeneous system.
- Szllsi, Gy?rgy,Hermán, Beáta,Szabados, Erika,Fül?p, Ferenc,Bartók, Mihály
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experimental part
p. 28 - 36
(2011/02/24)
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- Reactions of carbonyl compounds in basic solutions. Part 34. The mechanism of the base-catalysed ring fission of 2,3-diphenylcycloprop-2-en-1-one
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The rate coefficients for the base-catalysed ring fission of a series of 2-phenyl-3-(2-, 3-or 4-substituted phenyllcycloprop-2-en-1-ones to give the corresponding (E)-2,3-diphenylacrylic acids have heen determined in water at 30.0 °C, as well as for the unsubstituted compound at 40.0, 50.0 and 60.0 °C. The effects of meta-and para-substituents on the rates have been correlated using the Hammett equation to give a reaction constant, p, equal to ca 1.2 at 30 °C. For the unsubstituted compound, the activation parameters have been calculated and the kinetic solvent isotope effect has been studied. The effects of ortho-substituents on the rates appear to be mainly polar, rather than steric, in origin. The evidence indicates a mechanistic pathway which proceeds by addition of hydroxide anion to the ketone, which is rate-determining. The adduct suffers ring fission to give the final product via a carbanionic intermediate.
- Bowden, Keith,Burgess, Emma J.
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p. 1594 - 1600
(2007/10/03)
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- Effect of substituents on the 13C NMR chemical shifts of para-substituted α-phenyl-β-pyridylacrylic acids
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The 13C NMR spectra of para-substituted α-phenylcinnamic and 3- and 4-pyridylacrylic acids, with a wide range of substituents effects, were determined in deuterated dimethylsulfoxide (DMSO-d6). The effect of substituents in both the α-phenyl and β-pyridine groups in these acids is investigated using linear free energy relationships and multiple regression analysis as applied to 13C NMR chemical shifts of the C(α) and C(β) of the ethylenic bond and the carboxylic group carbon. Dissection of the α-phenyl substituent effects into the inductive and resonance components, using the dual substituent parameter (DSP) method, points to a blend of inductive and resonance effects in the π-electronic system.
- Jovanovi?,Mi?i?-Vukovi?,Drmani?,?anadi
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