149496-37-7

Basic information

• Product Name: 2-Azetidinone,3-amino-4-methyl-,trans-(9CI)
• Synonyms: 2-Azetidinone,3-amino-4-methyl-,trans-(9CI)
• CAS NO: 149496-37-7
• Molecular Formula: C4H8N2O
• Molecular Weight: 100.12
• Product Categories: VARIOUSAMINE
• Mol File: 149496-37-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 282.8±33.0 °C(Predicted)
• Appearance: /
• Density: 1.099±0.06 g/cm3(Predicted)
• PKA: 15.07±0.60(Predicted)
• CAS DataBase Reference: 2-Azetidinone,3-amino-4-methyl-,trans-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone,3-amino-4-methyl-,trans-(9CI)(149496-37-7)
• EPA Substance Registry System: 2-Azetidinone,3-amino-4-methyl-,trans-(9CI)(149496-37-7)

Safety Data

• Hazardous Substances Data: 149496-37-7(Hazardous Substances Data)

Upstream product

• 80582-05-4 (3R,4R)-3-(benzyloxycarbonylamino)-4-methyl-azetidin-2-one 
• 745074-58-2 trans-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-4-methylazetidin-2-one 
• 80582-04-3 (3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone 

Relevant articles and documents

Potent α-amino-β-lactam carbamic acid ester as NAAA inhibitors. Synthesis and structure-activity relationship (SAR) studies

4-Cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate (3b) is a potent, selective and systemically active inhibitor of intracellular NAAA activity, which produces profound anti-inflammatory effects in animal models. In the present work, we describe structure-activity relationship (SAR) studies on 3-aminoazetidin-2-one derivatives, which have led to the identification of 3b, and expand these studies to elucidate the principal structural and stereochemical features needed to achieve effective NAAA inhibition. Investigations on the influence of the substitution at the β-position of the 2-oxo-3-azetidinyl ring as well as on the effect of size and shape of the carbamic acid ester side chain led to the discovery of 3ak, a novel inhibitor of human NAAA that shows an improved physicochemical and drug-like profile relative to 3b. This favourable profile, along with the structural diversity of the carbamic acid chain of 3b, identify this compound as a promising new tool to investigate the potential of NAAA inhibitors as therapeutic agents for the treatment of pain and inflammation.

Asymmetric synthesis of trans-3-amino-4-alkylazetidin-2-ones from chiral N,N-dialkylhydrazones

Enantiopure N,N-dialkylhydrazones 3 smoothly react with N-benzyloxycarbonyl-N-benzyl glycine as an aminoketene precursor to afford trans-3-amino-4-alkylazetidin-2-ones 4 as single diasteromers. As an exception, hydrazone 3f (R = OBn) affords cis-(3R,4R)-4

The Synthesis of Substituted thio>acetic Acids

The synthesis of substituted thio>acetic acids (6, thiamazins) is described.Various substituted 3(S)-(acylamino)-2-azetidinones were sulfenylated with tert-butyl (phtalimidothio)acetate.Deprotection of the tert-butyl ester with trifluoroacetic acid provided the title compounds.In sharp contrast to their oxygen analogues (oxamazins), the thiamazins were devoid of biological activity.