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930-21-2,MFCD00013328
Catalog No.:AA00331U

930-21-2 | 2-Azetidinone

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00331U
Chemical Name:
2-Azetidinone
CAS Number:
930-21-2
Molecular Formula:
C3H5NO
Molecular Weight:
71.0779
MDL Number:
MFCD00013328
SMILES:
C1CNC1=O
Properties
Properties
 
BP:
222.434 °C at 760 mmHg  
Form:
Solid  
MP:
74-76 °C(lit.)  
Refractive Index:
1.4035 (estimate)  
Solubility:
chloroform: very soluble(lit.)  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
59.9  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
5  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
XLogP3:
-0.8  

Literature

Title: Ring splitting of azetidin-2-ones via radical anions.

Journal: Organic & biomolecular chemistry 20121021

Title: An expeditious iodine-catalyzed synthesis of 3-pyrrole-substituted 2-azetidinones.

Journal: Molecules (Basel, Switzerland) 20120928

Title: The vascular targeting agent Combretastatin-A4 directly induces autophagy in adenocarcinoma-derived colon cancer cells.

Journal: Biochemical pharmacology 20120901

Title: Photoelectron spectra of some antibiotic building blocks: 2-azetidinone and thiazolidine-carboxylic acid.

Journal: The journal of physical chemistry. A 20120823

Title: An expeditious route to eight-membered heterocycles by nickel-catalyzed cycloaddition: low-temperature C(sp)2-C(sp)3 bond cleavage.

Journal: Angewandte Chemie (International ed. in English) 20120820

Title: Kappa agonist CovX-Bodies.

Journal: Bioorganic & medicinal chemistry letters 20120615

Title: Regioselective cycloaddition of 3-azetidinones and 3-oxetanones with alkynes through nickel-catalysed carbon-carbon bond activation.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120319

Title: Novel pyrazole derivatives as anticancer and radiosensitizing agents.

Journal: Arzneimittel-Forschung 20120301

Title: Binding of β-lactam antibiotics to a bioinspired dizinc complex reminiscent of the active site of metallo-β-lactamases.

Journal: Inorganic chemistry 20120220

Title: Synthesis, in vitro antitubercular activity and 3D-QSAR of novel quinoxaline derivatives.

Journal: Chemical biology & drug design 20111201

Title: Synthesis and bioactivities of 2-azetidinone derivatives as cholesterol absorption inhibitors.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20111101

Title: Antibacterial agents and cystic fibrosis: synthesis and antimicrobial evaluation of a series of N-thiomethylazetidinones.

Journal: ChemMedChem 20111004

Title: (E)-4-Phenyl-butan-2-one oxime.

Journal: Acta crystallographica. Section E, Structure reports online 20110901

Title: A formal synthesis of ezetimibe via cycloaddition/rearrangement cascade reaction.

Journal: The Journal of organic chemistry 20110819

Title: Antiplasmodial and cytotoxicity evaluation of 3-functionalized 2-azetidinone derivatives.

Journal: Bioorganic & medicinal chemistry letters 20110801

Title: Poly[(μ(3)-rac-5-eth-oxy-carbonyl-6-hy-droxy-6-methyl-4-phenyl-4,5,6,7-tetra-hydro-benzo[c]isoxazol-3-olato)potassium].

Journal: Acta crystallographica. Section E, Structure reports online 20110601

Title: Development of biomimetic catalytic oxidation methods and non-salt methods using transition metal-based acid and base ambiphilic catalysts.

Journal: Proceedings of the Japan Academy. Series B, Physical and biological sciences 20110511

Title: Synthesis of spirocyclic β-keto-lactams: copper catalyzed process.

Journal: Chemical communications (Cambridge, England) 20110507

Title: Synthesis, evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones.

Journal: Bioorganic & medicinal chemistry 20110401

Title: 1-(4-Meth-oxy-phen-yl)-4-(3-nitro-phen-yl)-3-phen-oxy-azetidin-2-one.

Journal: Acta crystallographica. Section E, Structure reports online 20110201

Title: Conventional and microwave assisted synthesis of 2-oxo-4-substituted aryl-azetidine derivatives of benzotriazole: a new class of biological compounds.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: Monocyclic β-lactams: new structures for new biological activities.

Journal: Current medicinal chemistry 20110101

Title: 3D QSAR pharmacophore modeling, in silico screening, and density functional theory (DFT) approaches for identification of human chymase inhibitors.

Journal: International journal of molecular sciences 20110101

Title: Synthesis and Antimicrobial Activities of Some New Azetidin-2-ones and Thiazolidin-4-ones.

Journal: Indian journal of pharmaceutical sciences 20110101

Title: Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents.

Journal: Journal of medicinal chemistry 20101223

Title: 2-Azetidinone--a new profile of various pharmacological activities.

Journal: European journal of medicinal chemistry 20101201

Title: Synthesis of chlorinated bicyclic C-fused tetrahydrofuro[3,2-c]azetidin-2-ones.

Journal: The Journal of organic chemistry 20101105

Title: Natural and synthetic inhibitors of kallikrein-related peptidases (KLKs).

Journal: Biochimie 20101101

Title: Ferrier-Petasis rearrangement of 4-(vinyloxy)azetidin-2-ones: an entry to carbapenams and carbacephams.

Journal: The Journal of organic chemistry 20101015

Title: T-type calcium channel blockers: spiro-piperidine azetidines and azetidinones-optimization, design and synthesis.

Journal: Bioorganic & medicinal chemistry letters 20100801

Title: Azetidinone-isothiazolidinones: stereoselective synthesis and antibacterial evaluation of new monocyclic beta-lactams.

Journal: Bioorganic & medicinal chemistry 20100501

Title: Synthesis, in-vitro antimicrobial and cytotoxic studies of novel azetidinone derivatives.

Journal: Archiv der Pharmazie 20100401

Title: Dietary phospholipids and intestinal cholesterol absorption.

Journal: Nutrients 20100201

Title: Suppressed beta-effect of silicon in 3-silylated monocyclic beta-lactams: the role of antiaromaticity.

Journal: Organic letters 20091217

Title: Design, synthesis and bioactivity of catechin/epicatechin and 2-azetidinone derived chimeric molecules.

Journal: Bioorganic & medicinal chemistry letters 20091215

Title: 2-Azetidinone derivatives: design, synthesis, in vitro anti-microbial, cytotoxic activities and DNA cleavage study.

Journal: European journal of medicinal chemistry 20091201

Title: Azetidinones as zinc-binding groups to design selective HDAC8 inhibitors.

Journal: ChemMedChem 20091201

Title: Molecular and crystalline structures of three (S)-4-alkoxycarbonyl-2-azetidinones containing long alkyl side chains from synchrotron X-ray powder diffraction data.

Journal: Acta crystallographica. Section B, Structural science 20091201

Title: Potential of ezetimibe in memory deficits associated with dementia of Alzheimer's type in mice.

Journal: Indian journal of pharmacology 20091201

Title: Lewis acid-assisted ene cyclization of 2-azetidinone-tethered enals: synthesis of enantiopure carbacepham derivatives.

Journal: Chemistry, an Asian journal 20091005

Title: (RS/SR)-2-Oxo-4-phenyl-azetidin-3-yl acetate.

Journal: Acta crystallographica. Section E, Structure reports online 20091001

Title: A catalytic asymmetric route to carbapenems.

Journal: Organic letters 20090820

Title: Studies on the cytotoxic activity of synthetic 2H-azirine-2-azetidinone compounds.

Journal: Chemico-biological interactions 20090715

Title: Synthesis and antifungal activity of 2-azetidinonyl-5-(2-benzoylphenoxy)methyl-1,3,4-oxadiazoles against seed-borne pathogens of Eleusine coracana (L.) Gaertn.

Journal: Pest management science 20090701

Title: Staudinger ketene-imine cycloaddition, RCM approach to macrocrocyclic bisazetidinones.

Journal: The Journal of organic chemistry 20090605

Title: Large ring 1,3-bridged 2-azetidinones: experimental and theoretical studies.

Journal: European journal of medicinal chemistry 20090501

Title: 2-Azetidinone derivatives: design, synthesis and evaluation of cholesterol absorption inhibitors.

Journal: European journal of medicinal chemistry 20090401

Title: Spiro-piperidine azetidinones as potent TRPV1 antagonists.

Journal: Bioorganic & medicinal chemistry letters 20090201

Title: Ring opening at N1-C2 bond of azetidin-2-ones by a molybdenum hydroxo-carbonyl complex: evidence from a computational study.

Journal: Dalton transactions (Cambridge, England : 2003) 20081207

Title: Deeper insight into the mechanism of the reaction of photogenerated metallaketenes and imines.

Journal: Journal of the American Chemical Society 20081022

Title: Beta-lactam type molecular scaffolds for antiproliferative activity: synthesis and cytotoxic effects in breast cancer cells.

Journal: Journal of enzyme inhibition and medicinal chemistry 20081001

Title: Ezetimibe-related myopathy: A systematic review.

Journal: Journal of clinical lipidology 20081001

Title: Base-induced sequential cyclization-rearrangement of enantioenriched 3-aminoalkanoates to five- and seven-membered lactams.

Journal: Chemistry, an Asian journal 20080901

Title: Drug delivery approaches to overcome bacterial resistance to beta-lactam antibiotics.

Journal: Expert opinion on drug delivery 20080901

Title: Novel syntheses of azetidines and azetidinones.

Journal: Chemical reviews 20080901

Title: Ethyl 1'-[1-(4-methoxyphenyl)-3-phenoxy-4-phenylazetidin-1-yl]-1,3-dioxo-2',3',5',6',7',7a'-hexahydroindan-2-spiro-3'-1'H-pyrrolizine-2'-carboxylate.

Journal: Acta crystallographica. Section E, Structure reports online 20080901

Title: Spectroscopic characterization of the 1-substituted 3,3-diphenyl-4-(2'-hydroxyphenyl)azetidin-2-ones: application of (13)C NMR, (1)H-(13)C COSY NMR and mass spectroscopy.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20080801

Title: 3-Alkenyl-2-azetidinones as fatty acid amide hydrolase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20080715

Title: Indium-mediated 1,2,4,5-hexatetraen-3-ylation of 4-acetoxy-2-azetidinones and their applications to the Diels-Alder reactions for the synthesis of 2-azetidinone derivatives.

Journal: The Journal of organic chemistry 20080704

Title: Total synthesis of (-)-kainic acid via intramolecular Michael addition: a second-generation route.

Journal: Organic letters 20080501

Title: 1-(4-Methoxy-phen-yl)-7-phenyl-3-(phenyl-selenylmeth-yl)perhydro-isoxazolo[2',3':1,2]pyrrolo[3,4-b]azetidine-6-spiro-2'-chroman-2,4'-dione.

Journal: Acta crystallographica. Section E, Structure reports online 20080501

Title: 2-[1-(4-Ethoxy-phen-yl)-2-oxo-4-styryl-azetidin-3-yl]isoindoline-1,3-dione.

Journal: Acta crystallographica. Section E, Structure reports online 20080501

Title: Identification of novel cannabinoid CB1 receptor antagonists by using virtual screening with a pharmacophore model.

Journal: Journal of medicinal chemistry 20080424

Title: Discovery of azetidinone acids as conformationally-constrained dual PPARalpha/gamma agonists.

Journal: Bioorganic & medicinal chemistry letters 20080315

Title: Anti-tubercular and anti-inflammatory activities of azetidin-2-one derivatives and their effects on the activity of Phospholipase A2.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20080301

Title: New regiocontrolled synthesis of functionalized pyrroles from 2-azetidinone-tethered allenols.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20080101

Title: Synthesis and Pharmacological Evaluation of Azetidin-2-ones and Thiazolidin-4-ones Encompassing Benzothiazole.

Journal: Indian journal of pharmaceutical sciences 20080101

Title: Antibacterial Activity of Barringtonia acutangula against Selected Urinary Tract Pathogens.

Journal: Indian journal of pharmaceutical sciences 20080101

Title: Synthesis and biological activity of N-substituted-3-chloro-2-azetidinones.

Journal: Molecules (Basel, Switzerland) 20071112

Title: Synthesis of novel N-(4-ethoxyphenyl) azetidin-2-ones and their oxidative N-deprotection by ceric ammonium nitrate.

Journal: Molecules (Basel, Switzerland) 20071025

Title: A minimalistic approach to identify substrate binding features in B1 Metallo-beta-lactamases.

Journal: Bioorganic & medicinal chemistry letters 20070915

Title: Inhibitory effect by new monocyclic 4-alkyliden-beta-lactam compounds on human platelet activation.

Journal: Platelets 20070801

Title: Synthesis of 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent.

Journal: Bioorganic & medicinal chemistry 20070415

Title: Interaction of beta-lactam carbenes with aryl isonitriles: an unprecedented rearrangement of 2-azetidinonylidene indoles to delta-carbolinones.

Journal: The Journal of organic chemistry 20070330

Title: Azetidinones as vasopressin V1a antagonists.

Journal: Bioorganic & medicinal chemistry 20070301

Title: Two new antifungal alkaloids produced by Streptoverticillium morookaense.

Journal: The Journal of antibiotics 20070301

Title: In vivo responsiveness to ezetimibe correlates with niemann-pick C1 like-1 (NPC1L1) binding affinity: Comparison of multiple species NPC1L1 orthologs.

Journal: Molecular pharmacology 20070101

Title: Ezetimibe analogs with a reorganized azetidinone ring: Design, synthesis, and evaluation of cholesterol absorption inhibitions.

Journal: Bioorganic & medicinal chemistry letters 20070101

Title: Indium-mediated selective introduction of a 1,3-butadien-2-yl group at the C4-position in 2-azetidinones and application of 1,3-diene-tethered 2-azetidinones in the Diels-Alder reaction.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: A theoretical proposal for the synthesis of carbapenems from 4-(2-propynyl)azetidinones promoted by [W(CO)5] as an alternative to the Ag+-assisted process.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20061016

Title: A theoretical study of rhodium(I) catalyzed carbonylative ring expansion of aziridines to beta-lactams: crucial activation of the breaking C-N bond by hyperconjugation.

Journal: The Journal of organic chemistry 20060915

Title: Structures of (S)-(-)-4-oxo-2-azetidinecarboxylic acid and 3-azetidinecarboxylic acid from powder synchrotron diffraction data.

Journal: Acta crystallographica. Section B, Structural science 20060801

Title: An ab initio study on the allene-isocyanic acid and ketene-vinylimine [2 + 2] cycloaddition reaction paths.

Journal: The journal of physical chemistry. A 20060316

Title: Synthesis of strained tricyclic beta-lactams by intramolecular [2+2] cycloaddition reactions of 2-azetidinone-tethered enallenols: control of regioselectivity by selective alkene substitution.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20060201

Title: The polymer-supported and combinatorial synthesis of beta-lactam compounds: an update.

Journal: Mini reviews in medicinal chemistry 20060101

Title: Rabbit small intestine does not contain an annexin II/caveolin 1 complex as a target for 2-azetidinone cholesterol absorption inhibitors.

Journal: Biochimica et biophysica acta 20060101

Title: Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Journal: The Journal of organic chemistry 20051209

Title: Synthesis of 2-azetidinones from 2-diazo-1, 2-diarylethanones and N-(2-thienylidene)imines as possible antimicrobial agents.

Journal: Farmaco (Societa chimica italiana : 1989) 20050901

Title: The indium-mediated selective introduction of allenyl and propargyl groups at the C4-position of 2-azetidinones and the AuCl3-catalyzed cyclization of 4-allenyl-2-azetidinones.

Journal: Angewandte Chemie (International ed. in English) 20050311

Title: 3,4-disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P3 elements for potency and selectivity.

Journal: Bioorganic & medicinal chemistry letters 20050301

Title: Synthesis and anti-tubulin activity of a 3'-(4-azidophenyl)-3'-dephenylpaclitaxel photoaffinity probe.

Journal: Journal of medicinal chemistry 20041216

Title: Ketopyrrolidines and ketoazetidines as potent dipeptidyl peptidase IV (DPP IV) inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20041115

Title: Ezetimibe--a new cholesterol-lowering drug.

Journal: Drug and therapeutics bulletin 20040901

Title: Beta-lactams as versatile synthetic intermediates for the preparation of heterocycles of biological interest.

Journal: Current medicinal chemistry 20040701

Title: Kinetics and mechanism of hydrolysis of N-acyloxymethyl derivatives of azetidin-2-one.

Journal: The Journal of organic chemistry 20040514

Title: Examination of the 1,4-disubstituted azetidinone ring system as a template for combretastatin A-4 conformationally restricted analogue design.

Journal: Bioorganic & medicinal chemistry letters 20040503

Title: Solid-phase synthesis and SAR of 4-carboxy-2-azetidinone mechanism-based tryptase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20040503

Title: Regioselective Baeyer-Villiger oxidation in 4-carbonyl-2-azetidinone series: a revisited route toward carbapenem precursor.

Journal: The Journal of organic chemistry 20040430

Title: Functionalized macrocycles from functionalized tetra-amines: pendent-arm macrocycles derived from dichloropivalic acid.

Journal: Inorganic chemistry 20040308

Title: Synthesis of optically pure highly functionalized gamma-lactams via 2-azetidinone-tethered iminophosphoranes.

Journal: The Journal of organic chemistry 20040206

Title: Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones.

Journal: Bioorganic & medicinal chemistry letters 20040105

Title: Synthesis and evaluation of N1/C4-substituted beta-lactams as PPE and HLE inhibitors.

Journal: Bioorganic & medicinal chemistry 20040102

Title: Synthesis of cryptophycins via an N-acyl-beta-lactam macrolactonization.

Journal: The Journal of organic chemistry 20031212

Title: Design of beta-lactams with mechanism based nonantibacterial activities.

Journal: Current medicinal chemistry 20030901

Title: Ezetimibe for management of hypercholesterolemia.

Journal: The Annals of pharmacotherapy 20030601

Title: Crystal structure of 3,3-dichloro-N-p-methoxyphenyl-4-(2-phenylstryl)-2-azetidinone.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20030601

Title: Synthesis of a biotin-tagged photoaffinity probe of 2-azetidinone cholesterol absorption inhibitors.

Journal: Bioorganic & medicinal chemistry 20030417

Title: Catalysts with mixed ligands on immobilized supports. Electronic and steric advantages.

Journal: Organic letters 20030220

Title: Ezetimibe.

Journal: American journal of cardiovascular drugs : drugs, devices, and other interventions 20030101

Title: Exploring solid-phase approaches for the preparation of new beta-lactams from amino acids.

Journal: Molecular diversity 20030101

Title: beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20021101

Title: Efficient and highly stereoselective synthesis of a beta-lactam inhibitor of the serine protease prostate-specific antigen.

Journal: Bioorganic & medicinal chemistry 20020601

Title: A stereoselective synthesis of BMS-262084, an azetidinone-based tryptase inhibitor.

Journal: The Journal of organic chemistry 20020531

Title: General approach for the stereocontrolled construction of the beta-lactam ring in amino acid-derived 4-alkyl-4-carboxy-2-azetidinones.

Journal: The Journal of organic chemistry 20020531

Title: SmI(2)-mediated cyclizations of derivatized beta-lactams for the highly diastereoselective construction of functionalized prolines.

Journal: The Journal of organic chemistry 20020419

Title: Water-assisted alkaline hydrolysis of monobactams: a theoretical study.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20020215

Title: Synthesis of iodinated biochemical tools related to the 2-azetidinone class of cholesterol absorption inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20020211

Title: Synthesis of fluorescent biochemical tools related to the 2-azetidinone class of cholesterol absorption inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20020211

Title: Cholesterol absorption inhibitors for the treatment of hypercholesterolaemia.

Journal: Drugs 20020101

Title: Synthesis of ferrocene-substituted 2-azetidinones.

Journal: The Journal of organic chemistry 20011228

Title: Design, synthesis and pharmacological evaluation of 3-benzylazetidine-2-one-based human chymase inhibitors.

Journal: Bioorganic & medicinal chemistry 20011101

Title: beta-Lactam derivatives as enzyme inhibitors: derivatives of (E)-2-[(RS)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylidene]propionic acid.

Journal: Die Pharmazie 20010901

Title: Metal-promoted allylation, propargylation, or allenylation of azetidine-2,3-diones in aqueous and anhydrous media. Application to the asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-beta-lactams.

Journal: The Journal of organic chemistry 20010727

Title: Crystal structure of 3,3-dichloro-N-p-methoxyphenyl-4-(2-phenylstryl)-2-azetidinone.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20010701

Title: Entry to new conformationally constrained amino acids. First synthesis of 3-unsubstituted 4-alkyl-4-carboxy-2-azetidinone derivatives via an intramolecular N(alpha)-C(alpha)-cyclization strategy.

Journal: The Journal of organic chemistry 20010518

Title: Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen.

Journal: Journal of medicinal chemistry 20010510

Title: Design, synthesis and stability of N-acyloxymethyl- and N-aminocarbonyloxymethyl-2-azetidinones as human leukocyte elastase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20010423

Title: Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.

Journal: Journal of molecular recognition : JMR 20010101

Title: Synthesis of trans-4-aryl-3-(omega-chloroalkyl) -2-azetidinones.

Journal: Mededelingen (Rijksuniversiteit te Gent. Fakulteit van de Landbouwkundige en Toegepaste Biologische Wetenschappen) 20010101

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