113452-72-5

Upstream product

• 79002-45-2 N-benzyloxycarbonyl-glycine 
• 621-84-1 O-benzyl carbamate 
• 110-00-9 furan 
• 127357-37-3 methyl 2-(benzyloxycarbonylamino)-2-methoxyacetate 

Downstream Products

• 321596-55-8 methyl 4,6-dibromo-3-hydroxypyridine-2-carboxylate 
• 70946-43-9 methyl 2-amino-2-(furan-2-yl)acetate 
• 109070-27-1 Acetic acid 2-benzyloxycarbonylamino-2-(2,5-dimethoxy-2,5-dihydro-furan-2-yl)-ethyl ester 
• 109070-31-7 Acetic acid 2-benzyloxycarbonylamino-2-(2,5-dimethoxy-tetrahydro-furan-2-yl)-ethyl ester 
• 109070-32-8 2-Acetoxymethyl-6-hydroxy-3-oxo-piperidine-1-carboxylic acid benzyl ester 
• 109070-23-7 Acetic acid 2-benzyloxycarbonylamino-2-furan-2-yl-ethyl ester 
• 139014-82-7 (S)-Benzyloxycarbonylamino-furan-2-yl-acetic acid 
• 139014-80-5 methyl (2R)-2-{[(benzyloxy)carbonyl]amino}-2-(furan-2-yl)acetate 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF 3-HYDROXYPICOLINIC ACIDS

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

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

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.

THE AZA-ACHMATOWICZ REARRANGEMENT: A ROUTE TO USEFUL BUILDING BLOCKS FOR N- CONTAINING STRUCTURES

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.