139014-80-5Relevant academic research and scientific papers
PROCESS FOR THE PREPARATION OF 3-HYDROXYPICOLINIC ACIDS
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Paragraph 0057-0058, (2016/02/03)
4,6-Dibromo-3-hydroxypicolinate esters are prepared from furan-2-yl aminoacetates in one chemical step by use of a bromination-rearrangement reaction.
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.
Highly enantioselective synthesis of orthogonally protected (2S)-2,3-diaminopropanoates through catalytic phase-transfer aza-Henry reaction
Kumaraswamy, Gullapalli,Pitchaiah, Arigala
, p. 1543 - 1550 (2011/10/08)
The syntheses of enantiomer-enriched orthogonally protected different (2S)-2,3-diaminopropanoates and unnatural furyl-substituted (tert-butoxy) carbonyl (Boc) as well as (benzyloxy)carbonyl (Cbz) protected amino acid esters are accomplished by means of an
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.
Chemoenzymic Synthesis of Chiral Furan Derivatives: Useful Building Blocks for Optically Active Structures
Drueckhammer, Dale G.,Barbas, Carlos F.,Nozaki, Kenji,Wong, Chi-Huey,Wood, Cynthia Y.,Ciufolini, Marco A.
, p. 1607 - 1611 (2007/10/02)
Practical procedures have been developed for the enantioselective reduction of 2-acetylfuran (6a) and 2-(trifluoroacetyl)furan (6b) to the corresponding carbinols (S)-1 and 7b with 88-90percent ee using Thermoanaerobium brockii alcohol dehydrogenase coupled with an NADPH regeneration system.Kinetic resolution of racemic (S)-1 via lipase-catalyzed esterification, followed by cholesterol esterase or lipase-catalyzed hydrolysis of the ester gives (R)-1 with 94percent ee.Conversion of (S)-1 to the dihydropyranones 4 and 5 without racemization has been illustrated.Enantioselectivehydrolysis of N-protected furylglycine methyl esters catalyzed by papain gave the unreacted esters and and the free acids (S form) both in 45percent yield and 97percent ee.The resolved furylglycines are excellent substrates for the synthesis of optically active synthons for alkaloids.
THE AZA-ACHMATOWICZ REARRANGEMENT: A ROUTE TO USEFUL BUILDING BLOCKS FOR N- CONTAINING STRUCTURES
Ciufolini, Marco A.,Wood, Cynthia Y.
, p. 5085 - 5088 (2007/10/02)
N-Acyl 2-furylamines were transformed into 2-alkyl-6-methoxy-hexahydropyridin-3-ones.The rearranged products are useful building blocks for the total synthesis of alkaloids and unusual aminoacids.
