80082-81-1

Basic information

• Product Name: Carbamic acid, (2-oxo-3-azetidinyl)-, phenylmethyl ester, (S)-
• CAS NO: 80082-81-1
• Molecular Formula: C11H12N2O3
• Molecular Weight: 220.228
• Mol File: 80082-81-1.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (2-oxo-3-azetidinyl)-, phenylmethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (2-oxo-3-azetidinyl)-, phenylmethyl ester, (S)-(80082-81-1)
• EPA Substance Registry System: Carbamic acid, (2-oxo-3-azetidinyl)-, phenylmethyl ester, (S)-(80082-81-1)

Safety Data

• Hazardous Substances Data: 80082-81-1(Hazardous Substances Data)

Upstream product

• 83105-75-3 (3S)-1-hydroxy-3-[[[(phenylmethyl)oxy]carbonyl]amino]-2-azetidinone 
• 501-53-1 benzyl chloroformate 
• 80582-10-1 (S)-3-Amino-2-azetidinone 
• 88144-08-5 O-acetyl-α-N-Cbz-L-serine hydroxamate 
• 88144-10-9 N-acetoxy-3-(Cbz-amino)-2-azetidinone 
• 88144-07-4 (S)-Nα-(benzyloxycarbonyl)serine hydroxamic acid 
• 71404-99-4 (S)-[1-(phenylmethyloxy)-2-oxo-3-azetidinyl]carbamic acid phenylmethyl ester 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 23536-59-6 <2S-<2α,5α,6β>>-3,3-dimethyl-7-oxo-6-<<(phenylmethoxy)carbonyl>amino>-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid 
• 84486-00-0 ((S)-3-Benzyloxycarbonylamino-2-oxo-azetidin-1-yl)-phosphonic acid dimethyl ester 
• 83879-99-6 methyl 2-((3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidin-2-on-1-yl)-3-methylbut-2-enoate 
• 96851-01-3 (2R) methyl 2-((3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidin-2-on-1-yl)-3-methylbut-3-enoate 
• 96947-34-1 6β-benzyloxycarbonylamino-1ξ-oxo-1λ⁴-penicillanic acid methyl ester 

Downstream Products

• 84486-00-0 ((S)-3-Benzyloxycarbonylamino-2-oxo-azetidin-1-yl)-phosphonic acid dimethyl ester 
• 113791-14-3 [(3S)-2-oxoazetidin-3-yl]ammonium acetate 
• 80082-47-9 (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt 
• 84486-32-8 (S)-[1-(diethoxyphosphinyl)-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester 
• 112334-64-2 (S)-[1-[[[[3-[[[1,4-Dihydro-5-hydroxy-4-oxo-1-(phenylmethyl)-2-pyridinyl]acetyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidin yl]carbamic acid, phenylmethyl ester, monosodium salt 
• 112334-39-1 (S)-[1-[[[[4-[[1,4-dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester 
• 112335-05-4 (3S)-1-[[[[[(1,4-Dihydro-5-hydroxy-4-oxo-2pyridinyl)methyl]amino]sulfonyl]amino]carbonyl]2-oxo-3-[[(phenylmethoxy)carbonyl]amino]azetidine 

Relevant articles and documents

Synthesis of cytotoxic 1,3,4-trisubstituted 2-azetidinones

A series of 1,3,4-trisubstituted and 3,4-disubstituted 2-azetidinones were synthesized in order to study the relation between their structure and biological characteristics. Study of the cytotoxic activity of these compounds revealed an anticancer effect

CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS

Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.

Serine and threonine β-lactones: A new class of hepatitis A virus 3C cysteine proteinase inhibitors

Hepatitis A virus (HAV) 3C enzyme is a cysteine proteinase essential for viral replication and infectivity and represents a target for the development of antiviral drugs. A number of serine and threonine β-lactones were synthesized and tested against HAV 3C proteinase. The D-N-Cbz-serine β-lactone 5a displays competitive reversible inhibition with a Ki value of 1.50 × 10-6 M. Its enantiomer, L-N-Cbz-serine β-lactone 5b is an irreversible inactivator with kinact = 0.70 min-1, KI = 1.84 × 10-4 M and kinact/KI = 3800 M-1 min-1. Mass spectrometry and HMQC NMR studies using 13C-labeled 5b show that inactivation of the enzyme occurs by nucleophilic attack of the cysteine thiol (Cys-172) at the β-position of the oxetanone ring. Although the N-Cbz-serine β-lactones 5a and 5b display potent inhibition, other related analogues with an N-Cbz side chain, such as the five-membered ring homoserine γ-lactones 14a and 14b, the four-membered ring β-lactam 33, 2-methylene oxetane 34, cyclobutanone 36, and 3-azetidinone 39, fail to give significant inhibition of HAV 3C proteinase, thus demonstrating the importance of the β-lactone ring for binding.