13115-43-0Relevant academic research and scientific papers
A novel decarbonylation of heterocyclic pyruvic acid derivatives using sodium perborate
Ramsden, Christopher A.,Sargent, Bruce J.,Walle, Christiaan D.
, p. 1901 - 1904 (1996)
Decarbonylation of imidazo-2-yl and pyrid-2-ylpyruvic acids giving the corresponding acetic acids has been achieved using aqueous sodium perborate at room temperature. It is proposed that intramolecular hydrogen bonding, which inhibits conventional decarbonylation, facilitates epoxidation and subsequent decarboxylation of the enol tautomers.
Enhancement of the enantioselectivity of penicillin G acylase from E. coli by 'substrate tuning'
Pohl,Waldmann
, p. 2963 - 2966 (1995)
The efficiency of penicillin G acylase catalyzed transformations is enhanced significantly with respect to reaction velocity, and in particular, stereoselectivity by appropriate 'substrate tuning', i.e. by the introduction of a nitrogen atom into the part of the substrates which is recognized by the enzyme.
FLUORESCENT DYE AGENT AND CARBOSTYRIL COMPOUND
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Paragraph 0147; 0148, (2019/04/03)
PROBLEM TO BE SOLVED: To provide a novel fluorescent dye agent. SOLUTION: A fluorescent dye agent contains a carbostyril compound represented by formula (1) [in the formula (1), R1 is H, a halogen atom, a hydroxyl group, a cyano group, a nitro group or the like; R2 is O; R3 is a halogen atom, a carboxyl group, an ester group, an amide group or the like; R4-R6 and R8 independently represent H, a halogen atom, a nitro group, a cyano group or the like, where mutually adjacent groups of R4-R8 may be bound to form a ring; R7 is H, a substituted or unsubstituted aliphatic group or the like]. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides
Baruah, Pranjal K.,Dinsmore, Jason,King, Amber M.,Salomé, Christophe,De Ryck, Marc,Kaminski, Rafal,Provins, Laurent,Kohn, Harold
supporting information; experimental part, p. 3551 - 3564 (2012/07/28)
N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero)aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model.
Merging the structural motifs of functionalized amino acids and α-Aminoamides: Compounds with Significant Anticonvulsant Activities
Salomé, Christophe,Salomé-Grosjean, Elise,Stables, James P.,Kohn, Harold
supporting information; experimental part, p. 3756 - 3771 (2010/07/16)
Functional amino acids (FAAs) and α-aminoamides (AAAs) are two classes of antiepileptic drugs (AEDs) that exhibit pronounced anticonvulsant activities. We combined key structural pharmacophores present in FAAs and AAAs to generate a new series of compounds and document that select compounds exhibit activity superior to either the prototypical FAA (lacosamide) or the prototypical AAA (safinamide) in the maximal electroshock (MES) seizure model in rats. A representative compound, (R)-N-4′-((3′′-fluoro) benzyloxy)benzyl 2-acetamido-3-methoxypropionamide ((R)-10), was tested in the MES (mice, ip), MES (rat, po), psychomotor 6 Hz (32 mA) (mice, ip), and hippocampal kindled (rat, ip) seizure tests providing excellent protection with ED50 values of 13, 14, ~10 mg/kg, and 12 mg/kg, respectively. In the rat sciatic nerve ligation model (ip), (R)-10 (12 mg/kg) provided an 11.2-fold attenuation of mechanical allodynia. In the mouse biphasic formalin pain model (ip), (R)-10 (15 mg/kg) reduced pain responses in the acute and the chronic inflammatory phases.
Electrosynthesis of arylalkanoic acids by oxidation of the corresponding arylalkanols at the Ni anode in aqueous alkali
Lyalin,Petrosyan
, p. 499 - 503 (2008/04/05)
The electrochemical synthesis of a series of aryl(aryloxy)alkanoic acids was carried out by the electrocatalytic oxidation of the corresponding alcohols with the general formula RCH2CH2OH (R = Ar, CH 2Ph, OPh) in an undivided cell at the NiOOH electrode in aqueous alkali. The efficiency of the process depends on the structure of the starting alcohols, particularly, on the donor-acceptor properties of the substituent R. These properties determine the possibility of the primarily formed RCH 2COO- anion to be oxidized forming by-products. The yield of the target acids upon the oxidation of 2-(2-hydroxyethyl)pyridine, 2-phenylethanol, 3-phenylpronan-1-ol, and 2-phenoxyethanol was 15, 53, 75, and 93%, respectively, based on the reacted alcohol.
Palladium-catalysed α-arylation of esters and amides under microwave conditions
Bentz, Emilie,Moloney, Mark G.,Westaway, Susan M.
, p. 7395 - 7397 (2007/10/03)
A rapid and convenient approach for the α-arylation of esters and amides using Reformatsky reagents under a microwave accelerated reaction protocol has been established.
Degenerate Transesterification of 3,5-Dimethylphenolate/3,5-Dimethylphenyl Esters in Weakly Polar, Aprotic Solvents. Reactions of Aggregates and Complex-Induced Proximity Effects
Jackman,Petrei,Smith
, p. 3451 - 3458 (2007/10/02)
The rates of exchange of the 3,5-dimethylphenolate ion between lithium 3,5-dimethylphenolate-d6 and a series of 3,5-dimethylphenyl esters have been determined in the weakly polar, aprotic solvents dioxolane, dimethoxyethane (DME), tetrahydrofuran (THF), and pyridine. The esters include the propionate, butyrate, methoxyacctate, β-methoxypropionate, 4-methoxybutyrate, 2-tetrahydrofuroate, 2-furoate, (N,N-dimethylamino)acetate, (methylthio)acetate, 2- and 4-pyridine-carboxylates, 2-pyridylacetate, 4-pyridylacetate, phenylacetate, andp-methoxy-,p-chloro-, and p-(trifluoromethyl)phenylacetates. The rates and kinetic orders of the reactions of 3,5-dimethylphenyl propionate in various solvents at 35°C gave the following second-order rate constants (104k2, L mol-1 sec-1) for the following major aggregate species: THF tetramer, 6.5; DME tetramer, 3.3 (40°C); dioxolane, 13, hexamer, 71; pyridine tetramer, 2.2, dimer, 29. For 3,5-dimethylphenyl β-methoxypropionate, the order of reactivity is dioxolane > DME > THF. These results are interpreted in terms of a preequilibrium in which a solvent on lithium in the tetramer is replaced by the ester. The rates of transesterification have been compared with the rates of hydrolysis in 30% aqueous ethanol for the above series of esters. Those esters that have a second Lewis base center proximal to the ester function show significantly increased reactivity in transesterification, which is attributed to a complex-induced proximity effect.
Stabilized radiolabelled compounds
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, (2008/06/13)
A stabilizer for radioactively labelled organic compounds has the general formula STR1 where R is C1 to C4 alkylene which may be OH substituted, m is 0 or 1 (i.e. R may be absent or present), X is carboxyl or sulphonyl e.g. COOH or SO3 H or a salt thereof and n is 1, 2 or 3. Radiolabelled compounds of biological origin, such as nucleotides and amino acids, may be stabilized either in solution or in the freeze-dried state. For example, L-[35 S]methionine may be stabilized to prevent formation of a 47 KD band in protein transcription/translation experiments.
2-(2-imidazolin-2-yl)-pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents
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, (2008/06/13)
There are provided novel 2-(2-imidazolin-2-yl)pyridine and quinoline compounds, a process and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.
