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274-76-0,MFCD00005553
Catalog No.:AA003QWO

274-76-0 | Imidazo[1,2-a]pyridine

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  • Technical Information
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Technical Information
Catalog Number:
AA003QWO
Chemical Name:
Imidazo[1,2-a]pyridine
CAS Number:
274-76-0
Molecular Formula:
C7H6N2
Molecular Weight:
118.1359
MDL Number:
MFCD00005553
SMILES:
c1ccc2n(c1)ccn2
Properties
Properties
 
BP:
97 - 98 °C at 3 mmHg  
Form:
Solid  
MP:
130 - 132 °C  
Refractive Index:
n20/D 1.626(lit.)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
103  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
1  
XLogP3:
1.8  

Literature

Title: Synthesis and structure activity relationship of imidazo[1,2-a]pyridine-8-carboxamides as a novel antimycobacterial lead series.

Journal: Bioorganic & medicinal chemistry letters 20130901

Title: Design and biological evaluation of imidazo[1,2-a]pyridines as novel and potent ASK1 inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20121215

Title: Novel codrugs with GABAergic activity for dopamine delivery in the brain.

Journal: International journal of pharmaceutics 20121101

Title: Discovery of 3-cyclopropylmethyl-7-(4-phenylpiperidin-1-yl)-8-trifluoromethyl[1,2,4]triazolo[4,3-a]pyridine (JNJ-42153605): a positive allosteric modulator of the metabotropic glutamate 2 receptor.

Journal: Journal of medicinal chemistry 20121025

Title: Four-component cascade heteroannulation of heterocyclic ketene aminals: synthesis of functionalized tetrahydroimidazo[1,2-a]pyridine derivatives.

Journal: The Journal of organic chemistry 20121019

Title: Pd(0)-catalyzed decarboxylative coupling and tandem C-H arylation/decarboxylation for the synthesis of heteroaromatic biaryls.

Journal: The Journal of organic chemistry 20121019

Title: Imidazo[1,2-a]pyridines susceptible to excited state intramolecular proton transfer: one-pot synthesis via an Ortoleva-King reaction.

Journal: The Journal of organic chemistry 20120706

Title: Imidazonaphthyridine systems (part 2): Functionalization of the phenyl ring linked to the pyridine pharmacophore and its replacement by a pyridinone ring produces intriguing differences in cytocidal activity.

Journal: European journal of medicinal chemistry 20120601

Title: Direct arylation of imidazo[1,2-a]pyridine at C-3 with aryl iodides, bromides, and triflates via copper(I)-catalyzed C-H bond functionalization.

Journal: Organic letters 20120406

Title: Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds.

Journal: Bioorganic & medicinal chemistry 20120401

Title: SAR-study on a new class of imidazo[1,2-a]pyridine-based inhibitors of 5-lipoxygenase.

Journal: Bioorganic & medicinal chemistry letters 20120301

Title: 2-(8-Bromo-imidazo[1,2-a]pyridin-2-yl)-N'-[(E)-4-diethyl-amino-2-hy-droxy-benzyl-idene]acetohydrazide dihydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20120301

Title: Molecular characterization of EP6--a novel imidazo[1,2-a]pyridine based direct 5-lipoxygenase inhibitor.

Journal: Biochemical pharmacology 20120115

Title: Reaction of β-lactam carbenes with 2-pyridyl isonitriles: a one-pot synthesis of 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines useful as fluorescent probes for mercury ion.

Journal: The Journal of organic chemistry 20110916

Title: Novel imidazo[1,2-a]pyridine based inhibitors of the IGF-1 receptor tyrosine kinase: optimization of the aniline.

Journal: Bioorganic & medicinal chemistry letters 20110815

Title: Discovery of novel imidazo[1,2-a]pyridines as inhibitors of the insulin-like growth factor-1 receptor tyrosine kinase.

Journal: Bioorganic & medicinal chemistry letters 20110815

Title: The vaporization enthalpies of 2- and 4-(N,N-dimethylamino)pyridine, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, imidazo[1,2-a]pyridine and 1,2,4-triazolo[1,5-a]pyrimidine by correlation-gas chromatography.

Journal: The journal of physical chemistry. B 20110714

Title: Ethyl 8-amino-6-bromoimidazo[1,2-a]pyridine-2-carb-oxy-late.

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

Title: A practical two-step synthesis of imidazo[1,2-a]pyridines from N-(prop-2-yn-1-yl)pyridin-2-amines.

Journal: Chemical communications (Cambridge, England) 20110507

Title: A base promoted cyclization of N-propargylaminopyridines. Synthesis of imidazo[1,2-a]pyridine derivatives.

Journal: Organic letters 20110506

Title: Design, synthesis and in vitro antimicrobial evaluation of novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs.

Journal: European journal of medicinal chemistry 20110501

Title: Theoretical study on phosphorescence efficiency and color tuning from orange to blue-green of Ir(III) complexes based on substituted 2-phenylimidazo[1,2-a]pyridine ligand.

Journal: Journal of computational chemistry 20110430

Title: Design and synthesis of imidazopyridine analogues as inhibitors of phosphoinositide 3-kinase signaling and angiogenesis.

Journal: Journal of medicinal chemistry 20110414

Title: 2-Methyl-6-(trifluoro-meth-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

Journal: Acta crystallographica. Section E, Structure reports online 20110301

Title: Pharmacologic Treatment with GABA(B) Receptor Agonist of Methamphetamine-Induced Cognitive Impairment in Mice.

Journal: Current neuropharmacology 20110301

Title: Copper(I)-mediated preparation of new pyrano[3',4':4,5]imidazo[1,2-a]pyridin-1-one compounds under mild palladium-free conditions.

Journal: Organic & biomolecular chemistry 20110221

Title: Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: A novel synthetic smoothened antagonist transiently inhibits pancreatic adenocarcinoma xenografts in a mouse model.

Journal: PloS one 20110101

Title: Post Groebke-Blackburn multicomponent protocol: synthesis of new polyfunctional imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine derivatives as potential antimicrobial agents.

Journal: European journal of medicinal chemistry 20101201

Title: Ethyl 8-(4-nitro-phen-yl)imidazo[1,2-a]pyridine-7-carboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20101201

Title: Pharmacophore modeling and 3D-QSAR analysis of phosphoinositide 3-kinase p110alpha inhibitors.

Journal: Journal of molecular modeling 20100901

Title: Intra-periaqueductal grey microinjections of an imidazo[1,2-b]pyridazine derivative, DM2, affects rostral ventromedial medulla cell activity and shows antinociceptive effect.

Journal: Neuropharmacology 20100301

Title: Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives.

Journal: European journal of medicinal chemistry 20100201

Title: Efficient one-pot synthetic protocols for iminosugar-bearing imidazo[1,2-a]pyridines from carbohydrates.

Journal: Carbohydrate research 20100126

Title: 3-(3-Aryloxyaryl)imidazo[1,2-a]pyridine sulfones as liver X receptor agonists.

Journal: Bioorganic & medicinal chemistry letters 20100115

Title: Novel one-pot three component reaction for the synthesis of [2-(alkylsulfanyl)imidazo[1,2-a]pyridin-3-yl](aryl)methanone.

Journal: Journal of combinatorial chemistry 20100101

Title: Palladium complexes of abnormal N-heterocyclic carbenes as precatalysts for the much preferred Cu-free and amine-free Sonogashira coupling in air in a mixed-aqueous medium.

Journal: Dalton transactions (Cambridge, England : 2003) 20091221

Title: Structure-activity relationship study of EphB3 receptor tyrosine kinase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091101

Title: Physicochemical properties and membrane interactions of anti-apoptotic derivatives 2-(4-fluorophenyl)-3-(pyridin-4-yl)imidazo[1,2-a]pyridine depending on the hydroxyalkylamino side chain length and conformation: an NMR and ESR study.

Journal: European journal of medicinal chemistry 20090901

Title: [5-(2-Fur-yl)-6-nitro-1,2,3,5,6,7-hexa-hydro-imidazo[1,2-a]pyridin-8-yl](phen-yl)methanone.

Journal: Acta crystallographica. Section E, Structure reports online 20090901

Title: Discovery of imidazo[1,2-a]pyridines as potent MCH1R antagonists.

Journal: Bioorganic & medicinal chemistry letters 20090815

Title: Orally active C-6 heteroaryl- and heterocyclyl-substituted imidazo[1,2-a]pyridine acid pump antagonists (APAs).

Journal: Bioorganic & medicinal chemistry letters 20090701

Title: 1-(2-Methyl-imidazo[1,2-a]pyridin-3-yl)-3,3-bis-(methyl-sulfan-yl)prop-2-enone monohydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20090701

Title: IRAK-4 inhibitors for inflammation.

Journal: Current topics in medicinal chemistry 20090501

Title: Phosphonocarboxylates inhibit the second geranylgeranyl addition by Rab geranylgeranyl transferase.

Journal: The Journal of biological chemistry 20090313

Title: DNA gyrase (GyrB)/topoisomerase IV (ParE) inhibitors: synthesis and antibacterial activity.

Journal: Bioorganic & medicinal chemistry letters 20090201

Title: Discovery and optimization of imidazo[1,2-a]pyridine inhibitors of insulin-like growth factor-1 receptor (IGF-1R).

Journal: Bioorganic & medicinal chemistry letters 20090201

Title: Synthesis and anticandidal activity of some imidazopyridine derivatives.

Journal: Journal of enzyme inhibition and medicinal chemistry 20081201

Title: Novel imidazo[1,2-a]naphthyridinic systems (part 1): synthesis, antiproliferative and DNA-intercalating activities.

Journal: European journal of medicinal chemistry 20081101

Title: Synthesis and antituberculosis activity of new hydrazide derivatives.

Journal: Archiv der Pharmazie 20081101

Title: Chemical-genetic profiling of imidazo[1,2-a]pyridines and -pyrimidines reveals target pathways conserved between yeast and human cells.

Journal: PLoS genetics 20081101

Title: IRAK-4 inhibitors. Part III: a series of imidazo[1,2-a]pyridines.

Journal: Bioorganic & medicinal chemistry letters 20080615

Title: IRAK-4 inhibitors. Part II: a structure-based assessment of imidazo[1,2-a]pyridine binding.

Journal: Bioorganic & medicinal chemistry letters 20080601

Title: N-(2-Phenyl-imidazo[1,2-a]pyridin-3-yl)acetamide.

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

Title: 2-Phenyl-imidazo[1,2-a]pyridine-3-carbaldehyde.

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

Title: Imidazo[1,2-a]pyridine derivatives as inhibitors of TNF-alpha expression in T cells.

Journal: Bioorganic & medicinal chemistry 20080201

Title: Switching of polymorph-dependent ESIPT luminescence of an imidazo[1,2-a]pyridine derivative.

Journal: Angewandte Chemie (International ed. in English) 20080101

Title: Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110alpha inhibitors.

Journal: Bioorganic & medicinal chemistry 20070901

Title: Recent progress in the pharmacology of imidazo[1,2-a]pyridines.

Journal: Mini reviews in medicinal chemistry 20070901

Title: Synthesis and SAR studies of potent imidazopyridine anticoccidial agents.

Journal: Bioorganic & medicinal chemistry letters 20070701

Title: Synthesis and biological evaluation of imidazo[1,2-a]pyridine derivatives as novel PI3 kinase p110alpha inhibitors.

Journal: Bioorganic & medicinal chemistry 20070101

Title: Efficient solid-phase synthesis of a library of imidazo[1,2-a]pyridine-8-carboxamides.

Journal: Journal of combinatorial chemistry 20070101

Title: Diversification of the three-component coupling of 2-aminoheterocycles, aldehydes, and isonitriles: efficient parallel synthesis of a diverse and druglike library of imidazo- and tetrahydroimidazo[1,2-a] heterocycles.

Journal: Journal of combinatorial chemistry 20070101

Title: A novel series of imidazo[1,2-a]pyridine derivatives as HIF-1alpha prolyl hydroxylase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20061101

Title: Synthesis and evaluation of two 18F-labeled imidazo[1,2-a]pyridine analogues as potential agents for imaging beta-amyloid in Alzheimer's disease.

Journal: Bioorganic & medicinal chemistry letters 20060601

Title: 8-Fluoroimidazo[1,2-a]pyridine: synthesis, physicochemical properties and evaluation as a bioisosteric replacement for imidazo[1,2-a]pyrimidine in an allosteric modulator ligand of the GABA A receptor.

Journal: Bioorganic & medicinal chemistry letters 20060315

Title: The cellular phenotype of AZ703, a novel selective imidazo[1,2-a]pyridine cyclin-dependent kinase inhibitor.

Journal: Molecular cancer therapeutics 20060301

Title: AZ703, an imidazo[1,2-a]pyridine inhibitor of cyclin-dependent kinases 1 and 2, induces E2F-1-dependent apoptosis enhanced by depletion of cyclin-dependent kinase 9.

Journal: Cancer research 20060101

Title: Synthesis of indeno-fused derivatives of quinolizinium salts, imidazo[1,2-a]pyridine, pyrido[1,2-a]indole, and 4h-quinolizin-4-one via benzannulated enyne-allenes.

Journal: The Journal of organic chemistry 20050819

Title: Fused heterocycles: synthesis of some new imidazo[1,2-a]- pyridine derivatives.

Journal: Molecules (Basel, Switzerland) 20040930

Title: Identification of photoproducts from imazosulfuron by HPLC.

Journal: Biomedical chromatography : BMC 20040901

Title: Studies on the synthesis and characterization of four trans-planaramineplatinum(II) complexes of the form trans-PtL(NH3)CL2 where L = 2-hydroxypyridine, 3-hydroxypyridine, imidazole, and imidazo(1,2-alpha)pyridine.

Journal: European journal of medicinal chemistry 20040801

Title: Phenylpiperazinylmethylheterocycle derivatives: synthesis and dopamine receptor binding profiles.

Journal: Archiv der Pharmazie 20040701

Title: Imidazo[1,2-a]pyridines. Part 2: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20040503

Title: Imidazo[1,2-b]pyridazines: a potent and selective class of cyclin-dependent kinase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20040503

Title: Design and synthesis of acyclic nucleoside analogs with chlorinated imidazo[1,2-a]pyridine bases.

Journal: Nucleosides, nucleotides & nucleic acids 20031001

Title: Imidazo[1,2-a]pyridines: a potent and selective class of cyclin-dependent kinase inhibitors identified through structure-based hybridisation.

Journal: Bioorganic & medicinal chemistry letters 20030915

Title: Solid-phase synthesis of imidazo[1,2-a]pyridine using sodium benzenesulfinate as a traceless linker.

Journal: Organic letters 20021031

Title: Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues.

Journal: Farmaco (Societa chimica italiana : 1989) 20021001

Title: Influence of 2-substituent on the activity of imidazo[1,2-a] pyridine derivatives against human cytomegalovirus.

Journal: Bioorganic & medicinal chemistry 20020401

Title: 3-Benzamido, ureido and thioureidoimidazo[1,2-a]pyridine derivatives as potential antiviral agents.

Journal: Chemical & pharmaceutical bulletin 20011201

Title: Heterocyclization of functionalized vinylic derivatives of imidazo.

Journal: The Journal of organic chemistry 20011005

Title: Solution structure of 2-(pyrido[1,2-e]purin-4-yl)amino-ethanol intercalated in the DNA duplex d(CGATCG)2.

Journal: Biochemistry 20010731

Title: Synthesis of imidazo[1,2-a]pyridine derivatives as antiviral agents.

Journal: Arzneimittel-Forschung 20010101

Title: A structure-activity relationship study of the affinity of selected imidazo[1,2-a]pyridine derivatives, congeners of zolpidem, for the omega 1-subtype of the benzodiazepine receptor.

Journal: Acta poloniae pharmaceutica 20010101

Title: Synthesis of acyclo-C-nucleosides in the imidazo[1,2-a]pyridine and pyrimidine series as antiviral agents.

Journal: Journal of medicinal chemistry 19960705

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Tags:274-76-0 Molecular Formula|274-76-0 MDL|274-76-0 SMILES|274-76-0 Imidazo[1,2-a]pyridine