- Stereoselective Synthesis of Vinylboronates by Rh-Catalyzed Borylation of Stereoisomeric Mixtures
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The stereoselective preparation of vinylboronates via rhodium-catalyzed borylation of E/Z mixtures of vinyl actetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh-catalyzed borylation-isomerization sequence. The isomerization of (Z)-vinylboronates to (E)-isomers was also demonstrated.
- Li, Shenhuan,Li, Jie,Xia, Tianlai,Zhao, Wanxiang
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supporting information
p. 462 - 468
(2019/03/28)
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- Enantioselective water-soluble iron-porphyrin-catalyzed epoxidation with aqueous hydrogen peroxide and hydroxylation with iodobenzene diacetate
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The asymmetric epoxidation of styrene derivatives by H2O 2 (or UHP) to give optically active epoxides (ee up to 81%) and hydroxylation of alkanes to give optically active secondary alcohols (ee up to 78%) were carried out in methanol and water using chiral water-soluble iron porphyrins as catalysts.
- Maux, Paul Le,Srour, Hassan F.,Simonneaux, Gérard
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experimental part
p. 5824 - 5828
(2012/09/11)
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- N-Propynyl analogs of β-phenylethylidenehydrazines: Synthesis and evaluation of effects on glycine, GABA, and monoamine oxidase
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A group of β-phenylethylidenehydrazines possessing a variety of substituents (Me, OMe, Cl, F, and CF3) at the ortho-, meta-, or para-positions of the phenyl ring, in conjunction with either a N-bis-(2-propynyl) or a N-mono-(2-propynyl) moiety, were synthesized and compared to the novel neuroprotective drug β-phenylethylidenehydrazine (PEH) with regard to their ability to inhibit the enzymes GABA-transaminase (GABA-T) and monoamine oxidase (MAO)-A and -B in vitro in brain tissue. Two of the analogs synthesized (mono- and bis-N-propynylPEH) were also studied ex vivo in rats to compare their effects to those of PEH with regard to ability to inhibit GABA-T and MAO and to change brain levels of several important amino acids. Unlike PEH, none of the new drugs inhibited GABA-T in vitro at 10 or 100 μM, and all of the drugs (including PEH) were poor inhibitors (at 10 μM) of MAO-A and -B in vitro. The two analogs studied ex vivo inhibited GABA-T to a lesser extent than PEH, unlike PEH that did not elevate brain levels of GABA, and inhibited MAO-A and -B more potently than PEH. Interestingly, unlike PEH, the two analogs caused marked increases in brain levels of glycine; because of the current interest in drugs that increase glycine availability in the brain as potential antipsychotic drugs, these two analogs now warrant further investigation.
- MacKenzie, Erin M.,Fassihi, Afshin,Davood, Asghar,Chen, Qiao-Hong,Rauw, Gillian,Rauw, Gail,Knaus, Edward E.,Baker, Glen B.
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experimental part
p. 8254 - 8263
(2009/04/07)
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- NAPHTHALENE DERIVATIVES AS MODULATORS OF THE GLUCOCORTICOID RECEPTOR
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The present invention relates to naphthalene derivatives of formula (I) that are modulators of the glucocorticoid receptor, and to processes for the preparation and use of the same.
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Page/Page column 126-127
(2008/06/13)
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- Design and biological evaluation of phenyl-substituted analogs of β-phenylethylidenehydrazine
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β-Phenylethylidenehydrazine (PEH) has been demonstrated previously to be an inhibitor of γ-aminobutyric acid transaminase (GABA-T) and to cause a marked increase in rat brain levels of GABA, a major neurotransmitter. A group of PEH analogs, possessing a variety of substituents (Me, OMe, Cl, F, and CF3) at the 2-, 3-, and 4-positions of the phenyl ring, were synthesized for evaluation as inhibitors of GABA-T. The details of the synthesis and chemical characterization of the analogs are described. Preliminary in vitro screening for GABA-T inhibition showed that all the analogs possessed activity against this enzyme, although substitution of CF3 at the 2- and 4-positions caused reduced activity. One of the drugs, 4-fluoro-β- phenylethylidenehydrazine, was investigated further ex vivo, where it was shown to inhibit GABA-T, elevate brain levels of GABA, and decrease levels of glutamine, similar to the profile observed previously for PEH.
- Sowa, Bernard,Rauw, Gillian,Davood, Asghar,Fassihi, Afshin,Knaus, Edward E.,Baker, Glen B.
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p. 4389 - 4395
(2007/10/03)
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- INHIBITORS OF MONOAMINE UPTAKE
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N,N-disubstituted 4-amino-piperidines of the general Formula (I) are inhibitors of the uptake of serotonin and/or norepinephrine and/or dopamine. As such, they may be useful for the treatment of disorders of the central and/or peripheral nervous system.
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