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Home > Imidazoles > 274-76-0
274-76-0 | Imidazo[1,2-a]pyridine
CAS No: 274-76-0 Catalog No: AG003QZG MDL No:MFCD00005553
Product Description
Catalog Number:
AG003QZG
Chemical Name:
Imidazo[1,2-a]pyridine
CAS Number:
274-76-0
Molecular Formula:
C7H6N2
Molecular Weight:
118.1359
MDL Number:
MFCD00005553
IUPAC Name:
imidazo[1,2-a]pyridine
InChI:
InChI=1S/C7H6N2/c1-2-5-9-6-4-8-7(9)3-1/h1-6H
InChI Key:
UTCSSFWDNNEEBH-UHFFFAOYSA-N
SMILES:
c1ccc2n(c1)ccn2
UNII:
G18ZBV2HXA
Properties
Complexity:
103
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
118.053g/mol
Formal Charge:
0
Heavy Atom Count:
9
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
118.139g/mol
Monoisotopic Mass:
118.053g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
17.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8
Literature
| Title | Journal |
|---|---|
| Synthesis and structure activity relationship of imidazo[1,2-a]pyridine-8-carboxamides as a novel antimycobacterial lead series. | Bioorganic & medicinal chemistry letters 20130901 |
| Design and biological evaluation of imidazo[1,2-a]pyridines as novel and potent ASK1 inhibitors. | Bioorganic & medicinal chemistry letters 20121215 |
| Novel codrugs with GABAergic activity for dopamine delivery in the brain. | International journal of pharmaceutics 20121101 |
| 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 of medicinal chemistry 20121025 |
| Four-component cascade heteroannulation of heterocyclic ketene aminals: synthesis of functionalized tetrahydroimidazo[1,2-a]pyridine derivatives. | The Journal of organic chemistry 20121019 |
| Pd(0)-catalyzed decarboxylative coupling and tandem C-H arylation/decarboxylation for the synthesis of heteroaromatic biaryls. | The Journal of organic chemistry 20121019 |
| Imidazo[1,2-a]pyridines susceptible to excited state intramolecular proton transfer: one-pot synthesis via an Ortoleva-King reaction. | The Journal of organic chemistry 20120706 |
| 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. | European journal of medicinal chemistry 20120601 |
| 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. | Organic letters 20120406 |
| 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. | Bioorganic & medicinal chemistry 20120401 |
| SAR-study on a new class of imidazo[1,2-a]pyridine-based inhibitors of 5-lipoxygenase. | Bioorganic & medicinal chemistry letters 20120301 |
| 2-(8-Bromo-imidazo[1,2-a]pyridin-2-yl)-N'-[(E)-4-diethyl-amino-2-hy-droxy-benzyl-idene]acetohydrazide dihydrate. | Acta crystallographica. Section E, Structure reports online 20120301 |
| Molecular characterization of EP6--a novel imidazo[1,2-a]pyridine based direct 5-lipoxygenase inhibitor. | Biochemical pharmacology 20120115 |
| 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. | The Journal of organic chemistry 20110916 |
| Novel imidazo[1,2-a]pyridine based inhibitors of the IGF-1 receptor tyrosine kinase: optimization of the aniline. | Bioorganic & medicinal chemistry letters 20110815 |
| Discovery of novel imidazo[1,2-a]pyridines as inhibitors of the insulin-like growth factor-1 receptor tyrosine kinase. | Bioorganic & medicinal chemistry letters 20110815 |
| 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. | The journal of physical chemistry. B 20110714 |
| Ethyl 8-amino-6-bromoimidazo[1,2-a]pyridine-2-carb-oxy-late. | Acta crystallographica. Section E, Structure reports online 20110601 |
| A practical two-step synthesis of imidazo[1,2-a]pyridines from N-(prop-2-yn-1-yl)pyridin-2-amines. | Chemical communications (Cambridge, England) 20110507 |
| A base promoted cyclization of N-propargylaminopyridines. Synthesis of imidazo[1,2-a]pyridine derivatives. | Organic letters 20110506 |
| Design, synthesis and in vitro antimicrobial evaluation of novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs. | European journal of medicinal chemistry 20110501 |
| 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 of computational chemistry 20110430 |
| Design and synthesis of imidazopyridine analogues as inhibitors of phosphoinositide 3-kinase signaling and angiogenesis. | Journal of medicinal chemistry 20110414 |
| 2-Methyl-6-(trifluoro-meth-yl)imidazo[1,2-a]pyridine-3-carbonitrile. | Acta crystallographica. Section E, Structure reports online 20110301 |
| Pharmacologic Treatment with GABA(B) Receptor Agonist of Methamphetamine-Induced Cognitive Impairment in Mice. | Current neuropharmacology 20110301 |
| Copper(I)-mediated preparation of new pyrano[3',4':4,5]imidazo[1,2-a]pyridin-1-one compounds under mild palladium-free conditions. | Organic & biomolecular chemistry 20110221 |
| Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors. | Bioorganic & medicinal chemistry letters 20110101 |
| A novel synthetic smoothened antagonist transiently inhibits pancreatic adenocarcinoma xenografts in a mouse model. | PloS one 20110101 |
| 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. | European journal of medicinal chemistry 20101201 |
| Ethyl 8-(4-nitro-phen-yl)imidazo[1,2-a]pyridine-7-carboxyl-ate. | Acta crystallographica. Section E, Structure reports online 20101201 |
| Pharmacophore modeling and 3D-QSAR analysis of phosphoinositide 3-kinase p110alpha inhibitors. | Journal of molecular modeling 20100901 |
| Intra-periaqueductal grey microinjections of an imidazo[1,2-b]pyridazine derivative, DM2, affects rostral ventromedial medulla cell activity and shows antinociceptive effect. | Neuropharmacology 20100301 |
| Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives. | European journal of medicinal chemistry 20100201 |
| Efficient one-pot synthetic protocols for iminosugar-bearing imidazo[1,2-a]pyridines from carbohydrates. | Carbohydrate research 20100126 |
| 3-(3-Aryloxyaryl)imidazo[1,2-a]pyridine sulfones as liver X receptor agonists. | Bioorganic & medicinal chemistry letters 20100115 |
| Novel one-pot three component reaction for the synthesis of [2-(alkylsulfanyl)imidazo[1,2-a]pyridin-3-yl](aryl)methanone. | Journal of combinatorial chemistry 20100101 |
| 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. | Dalton transactions (Cambridge, England : 2003) 20091221 |
| Structure-activity relationship study of EphB3 receptor tyrosine kinase inhibitors. | Bioorganic & medicinal chemistry letters 20091101 |
| 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. | European journal of medicinal chemistry 20090901 |
| [5-(2-Fur-yl)-6-nitro-1,2,3,5,6,7-hexa-hydro-imidazo[1,2-a]pyridin-8-yl](phen-yl)methanone. | Acta crystallographica. Section E, Structure reports online 20090901 |
| Discovery of imidazo[1,2-a]pyridines as potent MCH1R antagonists. | Bioorganic & medicinal chemistry letters 20090815 |
| Orally active C-6 heteroaryl- and heterocyclyl-substituted imidazo[1,2-a]pyridine acid pump antagonists (APAs). | Bioorganic & medicinal chemistry letters 20090701 |
| 1-(2-Methyl-imidazo[1,2-a]pyridin-3-yl)-3,3-bis-(methyl-sulfan-yl)prop-2-enone monohydrate. | Acta crystallographica. Section E, Structure reports online 20090701 |
| IRAK-4 inhibitors for inflammation. | Current topics in medicinal chemistry 20090501 |
| Phosphonocarboxylates inhibit the second geranylgeranyl addition by Rab geranylgeranyl transferase. | The Journal of biological chemistry 20090313 |
| DNA gyrase (GyrB)/topoisomerase IV (ParE) inhibitors: synthesis and antibacterial activity. | Bioorganic & medicinal chemistry letters 20090201 |
| Discovery and optimization of imidazo[1,2-a]pyridine inhibitors of insulin-like growth factor-1 receptor (IGF-1R). | Bioorganic & medicinal chemistry letters 20090201 |
| Synthesis and anticandidal activity of some imidazopyridine derivatives. | Journal of enzyme inhibition and medicinal chemistry 20081201 |
| Novel imidazo[1,2-a]naphthyridinic systems (part 1): synthesis, antiproliferative and DNA-intercalating activities. | European journal of medicinal chemistry 20081101 |
| Synthesis and antituberculosis activity of new hydrazide derivatives. | Archiv der Pharmazie 20081101 |
| Chemical-genetic profiling of imidazo[1,2-a]pyridines and -pyrimidines reveals target pathways conserved between yeast and human cells. | PLoS genetics 20081101 |
| IRAK-4 inhibitors. Part III: a series of imidazo[1,2-a]pyridines. | Bioorganic & medicinal chemistry letters 20080615 |
| IRAK-4 inhibitors. Part II: a structure-based assessment of imidazo[1,2-a]pyridine binding. | Bioorganic & medicinal chemistry letters 20080601 |
| N-(2-Phenyl-imidazo[1,2-a]pyridin-3-yl)acetamide. | Acta crystallographica. Section E, Structure reports online 20080501 |
| 2-Phenyl-imidazo[1,2-a]pyridine-3-carbaldehyde. | Acta crystallographica. Section E, Structure reports online 20080501 |
| Imidazo[1,2-a]pyridine derivatives as inhibitors of TNF-alpha expression in T cells. | Bioorganic & medicinal chemistry 20080201 |
| Switching of polymorph-dependent ESIPT luminescence of an imidazo[1,2-a]pyridine derivative. | Angewandte Chemie (International ed. in English) 20080101 |
| Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110alpha inhibitors. | Bioorganic & medicinal chemistry 20070901 |
| Recent progress in the pharmacology of imidazo[1,2-a]pyridines. | Mini reviews in medicinal chemistry 20070901 |
| Synthesis and SAR studies of potent imidazopyridine anticoccidial agents. | Bioorganic & medicinal chemistry letters 20070701 |
| Synthesis and biological evaluation of imidazo[1,2-a]pyridine derivatives as novel PI3 kinase p110alpha inhibitors. | Bioorganic & medicinal chemistry 20070101 |
| Efficient solid-phase synthesis of a library of imidazo[1,2-a]pyridine-8-carboxamides. | Journal of combinatorial chemistry 20070101 |
| 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 of combinatorial chemistry 20070101 |
| A novel series of imidazo[1,2-a]pyridine derivatives as HIF-1alpha prolyl hydroxylase inhibitors. | Bioorganic & medicinal chemistry letters 20061101 |
| Synthesis and evaluation of two 18F-labeled imidazo[1,2-a]pyridine analogues as potential agents for imaging beta-amyloid in Alzheimer's disease. | Bioorganic & medicinal chemistry letters 20060601 |
| 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. | Bioorganic & medicinal chemistry letters 20060315 |
| The cellular phenotype of AZ703, a novel selective imidazo[1,2-a]pyridine cyclin-dependent kinase inhibitor. | Molecular cancer therapeutics 20060301 |
| 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. | Cancer research 20060101 |
| 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. | The Journal of organic chemistry 20050819 |
| Fused heterocycles: synthesis of some new imidazo[1,2-a]- pyridine derivatives. | Molecules (Basel, Switzerland) 20040930 |
| Identification of photoproducts from imazosulfuron by HPLC. | Biomedical chromatography : BMC 20040901 |
| 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. | European journal of medicinal chemistry 20040801 |
| Phenylpiperazinylmethylheterocycle derivatives: synthesis and dopamine receptor binding profiles. | Archiv der Pharmazie 20040701 |
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| Imidazo[1,2-b]pyridazines: a potent and selective class of cyclin-dependent kinase inhibitors. | Bioorganic & medicinal chemistry letters 20040503 |
| Design and synthesis of acyclic nucleoside analogs with chlorinated imidazo[1,2-a]pyridine bases. | Nucleosides, nucleotides & nucleic acids 20031001 |
| Imidazo[1,2-a]pyridines: a potent and selective class of cyclin-dependent kinase inhibitors identified through structure-based hybridisation. | Bioorganic & medicinal chemistry letters 20030915 |
| Solid-phase synthesis of imidazo[1,2-a]pyridine using sodium benzenesulfinate as a traceless linker. | Organic letters 20021031 |
| Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues. | Farmaco (Societa chimica italiana : 1989) 20021001 |
| Influence of 2-substituent on the activity of imidazo[1,2-a] pyridine derivatives against human cytomegalovirus. | Bioorganic & medicinal chemistry 20020401 |
| 3-Benzamido, ureido and thioureidoimidazo[1,2-a]pyridine derivatives as potential antiviral agents. | Chemical & pharmaceutical bulletin 20011201 |
| Heterocyclization of functionalized vinylic derivatives of imidazo. | The Journal of organic chemistry 20011005 |
| Solution structure of 2-(pyrido[1,2-e]purin-4-yl)amino-ethanol intercalated in the DNA duplex d(CGATCG)2. | Biochemistry 20010731 |
| Synthesis of imidazo[1,2-a]pyridine derivatives as antiviral agents. | Arzneimittel-Forschung 20010101 |
| 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. | Acta poloniae pharmaceutica 20010101 |
| Synthesis of acyclo-C-nucleosides in the imidazo[1,2-a]pyridine and pyrimidine series as antiviral agents. | Journal of medicinal chemistry 19960705 |
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