80582-10-1

Basic information

• Product Name: (S)-3-AMino-2-azetidinone
• Synonyms: (S)-3-AMino-2-azetidinone;2-Azetidinone, 3-amino-, (3S)-;(3S)-3-amino-2-Azetidinone;(S)-3-aminoazetidin-2-one;(3S)3AMINOAZETIDIN2ONE
• CAS NO: 80582-10-1
• Molecular Formula: C₃H₆N₂O
• Molecular Weight: 86.09254
• Mol File: 80582-10-1.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: (S)-3-AMino-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMino-2-azetidinone(80582-10-1)
• EPA Substance Registry System: (S)-3-AMino-2-azetidinone(80582-10-1)

Safety Data

• Hazardous Substances Data: 80582-10-1(Hazardous Substances Data)

Usage

General Description

(S)-3-Amino-2-azetidinone, also known as AAZ, is a chemical compound that consists of a four-membered ring containing an azetidine moiety and an amino group. It is an important intermediate in the synthesis of various biologically active compounds, such as pharmaceuticals and agrochemicals. AAZ is a versatile building block in organic synthesis, and its derivatives exhibit a wide range of pharmacological activities, including antibacterial, antifungal, and antiviral properties. (S)-3-AMino-2-azetidinone is also being studied for its potential use in the treatment of neurological disorders and cancer. Additionally, (S)-3-Amino-2-azetidinone is used as a chiral ligand in organic synthesis and as a reagent in the preparation of complex organic molecules.

Upstream product

• 88164-19-6 (S)-3-(Triphenylmethylamino)azetidin-2-one 
• 72229-74-4 (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]azetidin-2-one 
• 307001-86-1 (S)-benzyl-(2-oxoazetidin-3-yl)carbamic acid benzyl ester 
• 80082-81-1 benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate 
• 59509-33-0 3-[(Phenylacetyl)amino]-2-azetidinone 

Downstream Products

• 87599-86-8 (3S)-3-(D-2-tert-butyldimethylsilyloxy-2-phenylacetamido)-2-azetidinone 
• 80582-13-4 (3S)-3-((Z)-2-methoxyimino-2-phenylacetamido)-2-azetidinone 
• 87599-79-9 (3S)-3-<2-(2-chloroacetamidothiazol-4-yl)acetamido>-2-azetidinone 
• 87599-88-0 (3S)-3-<<3-(2,6-dichlorophenyl)-5-methylisoxazol-4-yl>carbonylamino>-2-azetidinone 
• 86583-25-7 (3S)-3-<2-(2-chloroacetamidothiazol-4-yl)-2-ureidoacetamido>-2-azetidinone 
• 78626-23-0 (3S)-3--2-azetidinone 
• 78611-36-6 (3S)-3--2-azetidinone 
• 87600-04-2 (3S)-3-<2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-trimethylsilylethoxycarbonylmethoxyimino)acetamido>-2-azetidonone 
• 1345827-34-0 (3S)-3-(N-fluorenyloxycarbonyl-L-phenylalanylamino)azetidin-2-one 
• 1345827-33-9 (3S)-3-(N-tert-butyloxycarbonyl-L-phenylalanylamino)azetidin-2-one 
• 80082-81-1 benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate 
• 125013-01-6 (S)-3-{[1-(4-Nitro-phenyl)-meth-(Z)-ylidene]-amino}-azetidin-2-one 

Relevant articles and documents

Preparation, gram-negative antibacterial activity, and hydrolytic stability of novel siderophore-conjugated monocarbam diols

A novel series of monocarbam compounds exhibiting promising antibacterial activity against multidrug resistant Gram-negative microorganisms is reported, along with the synthesis of one such molecule MC-1 (1). Also reported are structure-activity relationships associated with the in vitro and in vivo efficacy of 1 and related analogues in addition to the hydrolytic stability of such compounds and possible implications thereof.

MONOCARBAMS

The invention relates to compounds of formula (I): wherein R1, R2, R3, R4, Rs, and R6 as defined herein. The invention also relates to pharmaceutical compositions and methods of treating bacterial infections using compounds of formula (I)

3-Acylamino-azetidin-2-one as a novel class of cysteine proteases inhibitors

A new class of inhibitors for cysteine proteases cathepsin B, L, K and S is described. These inhibitors are based on the β-lactam ring designed to interact with the nucleophilic thiol of the cysteine in the active site of cysteine proteases. Some 3-acylamino-azetidin-2-one derivatives showed very potent inhibition activities for cathepsins L, K and S at the nanomolar or subnanomolar IC50 values.