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Azetidine

CAS No.:
503-29-7
Catalog Number:
AG003687
Molecular Formula:
C3H7N
Molecular Weight:
57.0944
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
95%
In Stock USA
United States
$48
- +
5g
95%
In Stock USA
United States
$169
- +
10g
95%
In Stock USA
United States
$319
- +
25g
95%
In Stock USA
United States
$613
- +
Product Description
Catalog Number:
AG003687
Chemical Name:
Azetidine
CAS Number:
503-29-7
Molecular Formula:
C3H7N
Molecular Weight:
57.0944
MDL Number:
MFCD00005165
IUPAC Name:
azetidine
InChI:
InChI=1S/C3H7N/c1-2-4-3-1/h4H,1-3H2
InChI Key:
HONIICLYMWZJFZ-UHFFFAOYSA-N
SMILES:
C1CCN1
EC Number:
207-963-8
UNII:
37S883XDWR
Properties
Complexity:
17.2  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
57.058g/mol
Formal Charge:
0
Heavy Atom Count:
4  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
57.096g/mol
Monoisotopic Mass:
57.058g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
12A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.1  
Literature
Title Journal
The azetidine derivative, KHG26792 protects against ATP-induced activation of NFAT and MAPK pathways through P2X7 receptor in microglia. Neurotoxicology 20151201
N-[4-(Azetidin-1-ylsulfon-yl)phen-yl]-N-(2,4-difluoro-benz-yl)acetamide. Acta crystallographica. Section E, Structure reports online 20121001
Exploration of novel 3-substituted azetidine derivatives as triple reuptake inhibitors. Journal of medicinal chemistry 20120927
Synthesis of cyclic polyamines by enzymatic generation of an amino aldehyde in situ. Macromolecular rapid communications 20120926
Method for the efficient synthesis of highly-substituted oxetan- and azetidin-, dihydrofuran- and pyrrolidin-3-ones and its application to the synthesis of (±)-pseudodeflectusin. Organic letters 20120921
Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol. Organic letters 20120817
Development of novel M1 antagonist scaffolds through the continued optimization of the MLPCN probe ML012. Bioorganic & medicinal chemistry letters 20120801
Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl)amines via intermediate azetidinium salts. The Journal of organic chemistry 20120720
Metabolic activation and major protein target of a 1-benzyl-3-carboxyazetidine sphingosine-1-phosphate-1 receptor agonist. Chemical research in toxicology 20120716
A network of ubiquitin ligases is important for the dynamics of misfolded protein aggregates in yeast. The Journal of biological chemistry 20120706
Identification of spirocyclic piperidine-azetidine inverse agonists of the ghrelin receptor. Bioorganic & medicinal chemistry letters 20120701
Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines. Organic & biomolecular chemistry 20120321
Fatty acid amide hydrolase inhibitors. 3: tetra-substituted azetidine ureas with in vivo activity. Bioorganic & medicinal chemistry letters 20120115
Highly efficient syntheses of azetidines, pyrrolidines, and indolines via palladium catalyzed intramolecular amination of C(sp3)-H and C(sp2)-H bonds at γ and δ positions. Journal of the American Chemical Society 20120111
Propolis prevents hepatorenal injury induced by chronic exposure to carbon tetrachloride. Evidence-based complementary and alternative medicine : eCAM 20120101
Effects of ring contraction on the conformational preferences of α-substituted proline analogs. Biopolymers 20120101
Development of an asymmetric trimethylenemethane cycloaddition reaction: application in the enantioselective synthesis of highly substituted carbocycles. Journal of the American Chemical Society 20111207
[3-Bromo-meth-yl-1-(4-methyl-phenyl-sulfon-yl)azetidin-3-yl]methanol. Acta crystallographica. Section E, Structure reports online 20111201
Total synthesis of gelsemoxonine. Journal of the American Chemical Society 20111109
Inhibition of nonmammalian glycosidases by azetidine iminosugars derived from stable 3,5-di-O-triflates of pentoses. Organic letters 20111104
Quantitative shotgun proteomics using a uniform ¹⁵N-labeled standard to monitor proteome dynamics in time course experiments reveals new insights into the heat stress response of Chlamydomonas reinhardtii. Molecular & cellular proteomics : MCP 20110901
Synthesis, biochemical and molecular modelling studies of antiproliferative azetidinones causing microtubule disruption and mitotic catastrophe. European journal of medicinal chemistry 20110901
Amine-promoted β-elimination of a β-aryloxy aldehyde for fluorogenic chemodosimeters. The Journal of organic chemistry 20110819
A theoretical rationale for why azetidine has a faster rate of formation than oxetane in TC(6-4) photoproducts. The journal of physical chemistry. B 20110811
Synthesis of new functionalized aziridine-2- and azetidine-3-carboxylic acid derivatives of potential interest for biological and foldameric applications. Amino acids 20110801
Synthesis and antibacterial activity of pentacyclines: a novel class of tetracycline analogs. Journal of medicinal chemistry 20110609
High-throughput scintillation proximity assay for stearoyl-CoA desaturase-1. Journal of biomolecular screening 20110601
Thermal decomposition mechanisms of methylamine, ethylamine, and 1-propylamine on Si(100)-2 × 1 surface. The Journal of chemical physics 20110521
Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using transition metal catalysis. Organic letters 20110401
Assessing the rates of ring-opening of aziridinium and azetidinium ions: a dramatic ring size effect. Organic letters 20110401
Synthesis of 3-methoxyazetidines via an aziridine to azetidine rearrangement and theoretical rationalization of the reaction mechanism. The Journal of organic chemistry 20110401
Polyazetidine-coated microelectrodes: electrochemical and diffusion characterization of different redox substrates. The journal of physical chemistry. B 20110210
A two-coordinate nickel imido complex that effects C−H amination. Journal of the American Chemical Society 20110202
Kinase inhibitors from marine sponges. Marine drugs 20110101
Evaluation of amide replacements in CCR5 antagonists as a means to increase intrinsic permeability. Part 2: SAR optimization and pharmacokinetic profile of a homologous azacyle series. Bioorganic & medicinal chemistry letters 20101115
3,3-Dinitro-azetidinium 2-hy-droxy-benzoate. Acta crystallographica. Section E, Structure reports online 20101101
Bisethylnorspermine lipopolyamine as potential delivery vector for combination drug/gene anticancer therapies. Pharmaceutical research 20100901
Link atom bond length effect in ONIOM excited state calculations. The Journal of chemical physics 20100807
In vivo and in vitro SAR of tetracyclic MAPKAP-K2 (MK2) inhibitors. Part II. Bioorganic & medicinal chemistry letters 20100801
Bangalore India Bio 2010. IDrugs : the investigational drugs journal 20100801
Azetidine derivatives as novel gamma-aminobutyric acid uptake inhibitors: synthesis, biological evaluation, and structure-activity relationship. European journal of medicinal chemistry 20100601
4-(2-Oxa-6-aza-spiro-[3.3]hept-6-yl)-benzo-nitrile. Acta crystallographica. Section E, Structure reports online 20100501
Lithiation-electrophilic substitution of N-thiopivaloylazetidine. Angewandte Chemie (International ed. in English) 20100406
Synthesis and antimycobacterial activity of azetidine-, quinazoline-, and triazolo-thiadiazole-containing pyrazines. Archiv der Pharmazie 20100401
Identification of a urea bioisostere of a triazole oxytocin antagonist. Bioorganic & medicinal chemistry letters 20100315
An efficient stereoselective synthesis of penaresidin a from (e)-2-protected amino-3,4-unsaturated sulfoxide. The Journal of organic chemistry 20100205
A theoretical study of dihydrogen bonds in small protonated rings: aziridine and azetidine cations. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20100201
Grp78 heterozygosity promotes adaptive unfolded protein response and attenuates diet-induced obesity and insulin resistance. Diabetes 20100101
Modulation of heat shock transcription factor 1 as a therapeutic target for small molecule intervention in neurodegenerative disease. PLoS biology 20100101
Targeted mutation of the mouse Grp94 gene disrupts development and perturbs endoplasmic reticulum stress signaling. PloS one 20100101
Biological activities of aqueous and organic extracts from tropical marine sponges. Marine drugs 20100101
Molecular mechanisms of ultraviolet radiation-induced DNA damage and repair. Journal of nucleic acids 20100101
Synthesis and evaluation of 1,3 di-substituted schiff, mannich bases and spiro isatin derivatives. Journal of young pharmacists : JYP 20100101
1-Benzoyl-3,3-dinitro-azetidine. Acta crystallographica. Section E, Structure reports online 20100101
The genus Gelsemium: An update. Pharmacognosy reviews 20100101
Discovery of azetidinyl ketolides for the treatment of susceptible and multidrug resistant community-acquired respiratory tract infections. Journal of medicinal chemistry 20091210
1-(2,4-Dinitro-phen-yl)-3,3-dinitro-azetidine. Acta crystallographica. Section E, Structure reports online 20091201
Silver(I)-catalyzed dual activation of propargylic alcohol and aziridine/azetidine: triggering ring-opening and endo-selective ring-closing in a cascade. The Journal of organic chemistry 20091120
Further evidence for 2-alkyl-2-carboxyazetidines as gamma-turn inducers. The Journal of organic chemistry 20091106
Structure based design of novel irreversible FAAH inhibitors. Bioorganic & medicinal chemistry letters 20091015
Striking reactivity of a stable, zwitterionic silylene towards substituted diazomethanes, azides, and isocyanides. Chemistry (Weinheim an der Bergstrasse, Germany) 20090824
Preparation of heteroaryloxetanes and heteroarylazetidines by use of a Minisci reaction. The Journal of organic chemistry 20090821
Synthesis of tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate. Organic letters 20090820
Fatty acid amide hydrolase inhibitors. Surprising selectivity of chiral azetidine ureas. Bioorganic & medicinal chemistry letters 20090801
Chemistry and pharmacology of nicotinic ligands based on 6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol (AMOP-H-OH) for possible use in depression. ChemMedChem 20090801
A practical method for targeted library design balancing lead-like properties with diversity. ChemMedChem 20090501
One-carbon ring expansion of azetidines via ammonium ylide [1,2]-shifts: a simple route to substituted pyrrolidines. The Journal of organic chemistry 20090403
Diastereoselective synthesis of bicyclic gamma-lactams via ring expansion of monocyclic beta-lactams. The Journal of organic chemistry 20090220
Functionalised azetidines as ligands: pyridyl-complemented coordination. Dalton transactions (Cambridge, England : 2003) 20090121
Functionalised azetidines as ligands: species derived by selective alkylation at substituent-nitrogen. Dalton transactions (Cambridge, England : 2003) 20090121
Synergistic apoptosis induction in leukemic cells by the phosphatase inhibitor salubrinal and proteasome inhibitors. PloS one 20090101
Regioselectivity control in the metal-catalyzed functionalization of gamma-allenols, part 2: Theoretical study. Chemistry (Weinheim an der Bergstrasse, Germany) 20090101
Synthesis of chiral organocatalysts derived from aziridines: application in asymmetric aldol reaction. The Journal of organic chemistry 20081205
Regio- and stereoselective ring opening of enantiomerically enriched 2-aryl oxetanes and 2-aryl azetidines with aryl borates. The Journal of organic chemistry 20081121
Cycloreversion of azetidines via oxidative electron transfer. steady-state and time-resolved studies. Organic letters 20081120
New chemistry of olefin complexes of platinum(II) unravelled by basic conditions: synthesis and properties of elusive cationic species. Dalton transactions (Cambridge, England : 2003) 20081021
Hsf1 is required for the nuclear translocation of p53 tumor suppressor. Neoplasia (New York, N.Y.) 20081001
Azetidine, pyrrolidine and hexamethyleneimine at 170 K. Acta crystallographica. Section C, Crystal structure communications 20081001
Activation of the unfolded protein response is required for defenses against bacterial pore-forming toxin in vivo. PLoS pathogens 20081001
Preparation of aryloxetanes and arylazetidines by use of an alkyl-aryl suzuki coupling. Organic letters 20080807
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. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20080801
Biodiversity of sphingoid bases ('sphingosines') and related amino alcohols. Journal of lipid research 20080801
Novel antibacterial azetidine lincosamides. Bioorganic & medicinal chemistry letters 20080415
N-alkyl-4-piperidinyl-2,3-diarylpyrrole derivatives with heterocyclic substitutions as potent and broad spectrum anticoccidial agents. Bioorganic & medicinal chemistry letters 20080315
Azetidine-derived amino acids versus proline derivatives. alternative trends in reverse turn induction. The Journal of organic chemistry 20080307
Theoretical studies on four-membered ring compounds with NF2, ONO2, N3, and NO2 groups. Journal of computational chemistry 20080301
Synthesis of New Quinolone Antibiotics Utilizing Azetidine Derivatives Obtained from 1-Azabicyclo[1.1.0]butane. Chemical & pharmaceutical bulletin 20080301
Role of biotransformation studies in minimizing metabolism-related liabilities in drug discovery. The AAPS journal 20080301
Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases. Journal of medicinal chemistry 20080227
RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines. Bioorganic & medicinal chemistry 20080115
Evaluation of enantiopure N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol for catalytic asymmetric addition of organozinc reagents to aldehydes. The Journal of organic chemistry 20080104
Pyrvinium targets the unfolded protein response to hypoglycemia and its anti-tumor activity is enhanced by combination therapy. PloS one 20080101
Direct organocatalytic synthesis of enantiopure succinimides from beta-lactam aldehydes through ring expansion promoted by azolium salt precatalysts. Chemical communications (Cambridge, England) 20071207
Convenient synthesis of trans-beta-amino carboxylic esters with an azetidine skeleton via rearrangement of beta,gamma-aziridino alpha-amino esters. Organic letters 20071011
A distal methyl substituent attenuates mitochondrial protein synthesis inhibition in oxazolidinone antibacterials. Bioorganic & medicinal chemistry letters 20070915
Synthesis of penaresidin derivatives and its biological activity. Bioorganic & medicinal chemistry 20070715
Electron-transfer induced repair of 6-4 photoproducts in DNA: a computational study. The journal of physical chemistry. A 20070329
N-nitrosation of amines by NO2 and NO: a theoretical study. The journal of physical chemistry. A 20070322
Synthesis and antibacterial activities of new quinolone derivatives utilizing 1-azabicyclo[1.1.0]butane. Bioorganic & medicinal chemistry letters 20070215
Intramolecular hydroamination/cyclisation of aminoallenes mediated by a neutral zirconocene catalyst: a computational mechanistic study. Chemistry (Weinheim an der Bergstrasse, Germany) 20070101
Azetidine-based inhibitors of dipeptidyl peptidase IV (DPP IV). Current topics in medicinal chemistry 20070101
NS-187 (INNO-406), a Bcr-Abl/Lyn dual tyrosine kinase inhibitor. Analytical chemistry insights 20070101
Synthesis and reactivity of azapalladacyclobutanes. Journal of the American Chemical Society 20061206
Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers. The Journal of organic chemistry 20061124
Reaction of azetidines with chloroformates. Organic letters 20061123
Cortisol can be pro- or anti-apoptotic in sea bream cells: potential role of HSP70 induction for cytoprotection. Molecular and cellular endocrinology 20061019
The profound effect of fluorine substitution on the reactivity and regioselectivity of nucleophilic substitution reactions of strained heterocycles. A study of aziridine and its derivatives. The Journal of organic chemistry 20061013
A practical and facile synthesis of azetidine derivatives for oral carbapenem, L-084. Chemical & pharmaceutical bulletin 20061001
Species differences in metabolism and pharmacokinetics of a sphingosine-1-phosphate receptor agonist in rats and dogs: formation of a unique glutathione adduct in the rat. Drug metabolism and disposition: the biological fate of chemicals 20060801
Structures of (S)-(-)-4-oxo-2-azetidinecarboxylic acid and 3-azetidinecarboxylic acid from powder synchrotron diffraction data. Acta crystallographica. Section B, Structural science 20060801
N,N'-carbonyldiimidazole-mediated cyclization of amino alcohols to substituted azetidines and other N-heterocycles. The Journal of organic chemistry 20060526
Electroreductive intramolecular coupling of aromatic imino esters: is four-membered cyclization much more favorable than six-membered cyclization? Organic letters 20060330
Ring transformation of 2-(haloalkyl)azetidines into 3,4-disubstituted pyrrolidines and piperidines. Organic letters 20060316
A study of anti-inflammatory activity of some novel alpha-amino naphthalene and beta-amino naphthalene derivatives. Archiv der Pharmazie 20060301
Mitsunobu dehydration of N-Boc neomycin B. Organic & biomolecular chemistry 20060107
Synthesis and structure of novel conformationally constrained 1',2'-azetidine-fused bicyclic pyrimidine nucleosides: their incorporation into oligo-DNAs and thermal stability of the heteroduplexes. The Journal of organic chemistry 20060106
Silylmethyl-substituted aziridine and azetidine as masked 1,3- and 1,4-dipoles for formal [3 + 2] and [4 + 2] cycloaddition reactions. Journal of the American Chemical Society 20051130
Ultrafast intramolecular charge transfer and internal conversion with tetrafluoro-aminobenzonitriles. Chemphyschem : a European journal of chemical physics and physical chemistry 20051111
Azetidinic amino acids: stereocontrolled synthesis and pharmacological characterization as ligands for glutamate receptors and transporters. Organic & biomolecular chemistry 20051107
New fluorinated pyrrolidine and azetidine amides as dipeptidyl peptidase IV inhibitors. Bioorganic & medicinal chemistry letters 20051101
Practical asymmetric preparation of azetidine-2-carboxylic acid. The Journal of organic chemistry 20051028
Comparing hypothetical structures generated in the third Cambridge blind test of crystal structure prediction. Acta crystallographica. Section B, Structural science 20051001
Differentiation of Leishmania donovani in host-free system: analysis of signal perception and response. Molecular and biochemical parasitology 20050501
Carbohydrate sulfonyl chlorides for simple, convenient access to glycoconjugates. Organic letters 20050317
An intramolecular 1,3-dipolar cycloaddition reaction towards the synthesis of chiral azetidine nucleoside analogues: the D-gluco case. Nucleosides, nucleotides & nucleic acids 20050101
Azetidine-induced accumulation of class I small heat shock proteins in the soluble fraction provides thermotolerance in soybean seedlings. Plant & cell physiology 20041201
Anionic NaCl-type frameworks of [Mn(II)(HCOO)(3)(-)], templated by alkylammonium, exhibit weak ferromagnetism. Dalton transactions (Cambridge, England : 2003) 20040807
Characterization of multiple members of the HSP70 family in platyfish culture cells: molecular evolution of stress protein HSP70 in vertebrates. Gene 20040721
Secondary electrospray ionization-ion mobility spectrometry for explosive vapor detection. Analytical chemistry 20040515
Synthesis of potent and highly selective nonguanidine azetidinone inhibitors of human tryptase. Bioorganic & medicinal chemistry letters 20040503
Synthesis and anti-HCMV activity of 1-acyl-beta-lactams and 1-acylazetidines derived from phenylalanine. Bioorganic & medicinal chemistry letters 20040503
Abnormal aza-Baylis-Hillman reaction of N-tosylated imines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one. Organic letters 20031127
Thermodynamic conformational analysis and structural stability of the nicotinic analgesic ABT-594. Journal of computer-aided molecular design 20031101
Asymmetric cyclization via memory of chirality: a concise access to cyclic amino acids with a quaternary stereocenter. Journal of the American Chemical Society 20031029
Cyclic amine sulfonamides as linkers in the design and synthesis of novel human beta(3) adrenergic receptor agonists. Bioorganic & medicinal chemistry letters 20030707
Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid. Organic letters 20030612
Conformationally restricted chiral peptide nucleic acids derived from azetidines. Nucleosides, nucleotides & nucleic acids 20030101
Structure-activity relationships of 1-alkyl-5-(3,4-dichlorophenyl)- 5-[2-[(3-substituted)-1-azetidinyl]ethyl]-2-piperidones. 1. Selective antagonists of the neurokinin-2 receptor. Journal of medicinal chemistry 20021121
Synthesis and structure-activity relationships of aminoalkylazetidines as ORL1 receptor ligands. Bioorganic & medicinal chemistry letters 20021104
Requirement of the p38 mitogen-activated protein kinase signalling pathway for the induction of the 78 kDa glucose-regulated protein/immunoglobulin heavy-chain binding protein by azetidine stress: activating transcription factor 6 as a target for stress-induced phosphorylation. The Biochemical journal 20020915
Synthesis and structure of an azatrisilacyclobutane and its precursor, a novel lithium enamide having a tricyclic (LiNSiO)2 skeleton. Angewandte Chemie (International ed. in English) 20020715
Stereoselective synthesis of functionalized gamma-amino esters: azetidinium salts and epoxy esters. Organic letters 20020418
Glucose deprivation induces heme oxygenase-1 gene expression by a pathway independent of the unfolded protein response. The Journal of biological chemistry 20020118
Differential accumulation of U14 snoRNA and hsc70 mRNA in Chinese hamster cells after exposure to various stress conditions. Cell stress & chaperones 20020101
[125/123I] 5-Iodo-3-pyridyl ethers. syntheses and binding to neuronal nicotinic acetylcholine receptors. Nuclear medicine and biology 20011101
Contribution of heat shock proteins to cell protection from complement-mediated lysis. International immunology 20010801
Secretion monitor, SecM, undergoes self-translation arrest in the cytosol. Molecular cell 20010101
Recombinant cell lines for stress reporter assays. Cell biology and toxicology 20010101
Induction of the DNA-binding and transcriptional activities of heat shock factor 1 is uncoupled in Xenopus oocytes. Biochimica et biophysica acta 19980312
Properties