875932-90-4

Basic information

• Product Name: Carbamic acid, [3-(1H-imidazol-1-yl)-3-oxopropyl]-, phenylmethyl ester
• CAS NO: 875932-90-4
• Molecular Formula: C14H15N3O3
• Molecular Weight: 273.291
• Mol File: 875932-90-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [3-(1H-imidazol-1-yl)-3-oxopropyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [3-(1H-imidazol-1-yl)-3-oxopropyl]-, phenylmethyl ester(875932-90-4)
• EPA Substance Registry System: Carbamic acid, [3-(1H-imidazol-1-yl)-3-oxopropyl]-, phenylmethyl ester(875932-90-4)

Safety Data

• Hazardous Substances Data: 875932-90-4(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 117290-25-2 methyl N-Cbz-β-alanylsulfonamide 
• 164223-35-2 ethyl 5-{[(benzyloxy)carbonyl]amino}-3-oxopentanoate 
• 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 

Relevant articles and documents

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.

VIGABATRIN BIOISOTERES AND RELATED METHODS OF USE

Compounds bioisoteric to vigabatrin and related methods of use.