875932-90-4

Upstream product

• 2304-94-1 3-(benzyloxycarbonylamino)propanoic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 505031-91-4 (E)-5-Benzyloxycarbonylamino-3-pyrrolidin-1-yl-pent-2-enoic acid ethyl ester 
• 164223-36-3 Ethyl 5-(2-benzyloxycarbonylaminoethyl)-3-methylisoxazole-4-carboxylate 
• 226704-28-5 5-(2-Benzyloxycarbonylaminoethyl)-3-methylisoxazole-4-carboxylic acid 
• 117290-25-2 methyl N-Cbz-β-alanylsulfonamide 
• 164223-35-2 ethyl 5-{[(benzyloxy)carbonyl]amino}-3-oxopentanoate 

Relevant academic research and scientific papers

New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity

A series of potential substrates of γ-aminobutyric acid aminotransferase (GABA-AT) with lipophilic bioisosteres of the carboxylic acid group (2-7) were synthesized and tested. Most of the synthesized compounds showed substrate activities with GABA-AT; 1H-tetrazole-5-propanamine (6) was the best of those tested. The potential time-dependent inhibitor of GABA-AT, 1H-tetrazole-5-(α-vinyl-propanamine) (8), was designed based on the structures of 6 and the antiepilepsy drug vigabatrin (4-aminohex-5-enoic acid, 1). The synthesized compound 8 showed time-dependent inhibition of GABA-AT, but its potency is lower than that of vigabatrin. Methylation of the tetrazole group in 8 resulted in loss of time-dependent activity, suggesting that the tetrazole ring, the carboxylate bioisostere, exists in its deprotonated form in the enzyme active site.

Multigram-scale synthesis of enantiopure 3,3-difluoroproline

An efficient route for the synthesis of enantiopure 3,3-difluoroproline on multigram-scale is described herein. The deoxofluorination can be achieved with DAST on the corresponding racemic pyrrolidinone in good yield. Resolution of the racemate by crystallization with D- and L-tyrosine hydrazide provides both enantiomers of 3,3-difluoroproline in high yield and ee%.

VIGABATRIN BIOISOTERES AND RELATED METHODS OF USE

Compounds bioisoteric to vigabatrin and related methods of use.

1,3-Dipolar cycloaddition route to nitrogen heterocyclic triones

1,3-Dipolar cycloaddition of nitrile oxides, formed in situ by dehydration of primary nitro compounds, with pyrrolidine enamines of protected γ- or δ-amino-β-keto esters affords isoxazole-4-carboxylates; these undergo lactam formation and N-O bond cleavage to afford 3-acyltetramic acids and 3-acyl-4-hydroxypyridin-2-ones.