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Home > Indoles and Oxindole > 271-63-6
271-63-6 | 7-Azaindole
CAS No: 271-63-6 Catalog No: AG0034DT MDL No:MFCD00005606
Product Description
Catalog Number:
AG0034DT
Chemical Name:
7-Azaindole
CAS Number:
271-63-6
Molecular Formula:
C7H6N2
Molecular Weight:
118.1359
MDL Number:
MFCD00005606
IUPAC Name:
1H-pyrrolo[2,3-b]pyridine
InChI:
InChI=1S/C7H6N2/c1-2-6-3-5-9-7(6)8-4-1/h1-5H,(H,8,9)
InChI Key:
MVXVYAKCVDQRLW-UHFFFAOYSA-N
SMILES:
c1cnc2c(c1)cc[nH]2
EC Number:
205-981-0
UNII:
QX4465NR9T
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:
1
Isotope Atom Count:
0
Molecular Weight:
118.139g/mol
Monoisotopic Mass:
118.053g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
28.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8
Literature
| Title | Journal |
|---|---|
| The acid-catalysed synthesis of 7-azaindoles from 3-alkynyl-2-aminopyridines and their antimicrobial activity. | Organic & biomolecular chemistry 20140114 |
| Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction. | Organic & biomolecular chemistry 20121128 |
| Theoretical study on water-mediated excited-state multiple proton transfer in 7-azaindole: significance of hydrogen bond rearrangement. | The journal of physical chemistry. A 20121101 |
| Excited state tautomerization of 7-azaindole in a 1:1 complex with δ-valerolactam: a comparative study with the homodimer. | The journal of physical chemistry. A 20121011 |
| How to modify 7-azaindole to form cytotoxic Pt(II) complexes: highly in vitro anticancer effective cisplatin derivatives involving halogeno-substituted 7-azaindole. | Journal of inorganic biochemistry 20121001 |
| N-[(3RS,4SR)-1-Benzyl-4-methyl-piperi-din-3-yl]-1-(4-methylphenyl-sulfonyl)-5-nitro-1H-pyrrolo-[2,3-b]pyridin-4-amine. | Acta crystallographica. Section E, Structure reports online 20121001 |
| Theoretical study of the excited-state double proton transfer in the (3-methyl-7-azaindole)-(7-azaindole) heterodimer. | Journal of computational chemistry 20120730 |
| Design, synthesis, and evaluation of 3,5-disubstituted 7-azaindoles as Trk inhibitors with anticancer and antiangiogenic activities. | Journal of medicinal chemistry 20120614 |
| Novel pyrazole derivatives as anticancer and radiosensitizing agents. | Arzneimittel-Forschung 20120301 |
| Synthesis and antibacterial activity against ralstonia solanacearum for novel hydrazone derivatives containing a pyridine moiety. | Chemistry Central journal 20120101 |
| Solvent effects in the excited-state tautomerization of 7-azaindole: a theoretical study. | The journal of physical chemistry. B 20111222 |
| Discovery and optimization of indoles and 7-azaindoles as Rho kinase (ROCK) inhibitors (part-I). | Bioorganic & medicinal chemistry letters 20111201 |
| Theoretical studies for excited-state tautomerization in the 7-azaindole-(CH3OH)n (n = 1 and 2) complexes in the gas phase. | The journal of physical chemistry. A 20111201 |
| Discovery and optimization of indole and 7-azaindoles as Rho kinase (ROCK) inhibitors (part-II). | Bioorganic & medicinal chemistry letters 20111201 |
| Direct functionalization of (un)protected tetrahydroisoquinoline and isochroman under iron and copper catalysis: two metals, two mechanisms. | The Journal of organic chemistry 20111104 |
| Structure of 7-azaindole···2-fluoropyridine dimer in a supersonic jet: competition between N-H···N and N-H···F interactions. | The journal of physical chemistry. A 20110922 |
| Structure-based design and optimization of potent renin inhibitors on 5- or 7-azaindole-scaffolds. | Bioorganic & medicinal chemistry letters 20110915 |
| Excited state electron transfer precedes proton transfer following irradiation of the hydrogen-bonded single water complex of 7-azaindole with UV light. | The Journal of chemical physics 20110828 |
| From insertion of rhodium acetate paddlewheels into functionalized 7-azaindole hydrogen-bonded dimers to infinite architectures. | Dalton transactions (Cambridge, England : 2003) 20110728 |
| Selectivity of kinase inhibitor fragments. | Journal of medicinal chemistry 20110728 |
| A theoretical study on excited state double proton transfer reaction of a 7-azaindole dimer: an ab initio potential energy surface and its empirical valence bond model. | Physical chemistry chemical physics : PCCP 20110621 |
| Synthesis and characterisation of group nine transition metal complexes containing new mesityl and naphthyl based azaindole scorpionate ligands. | Dalton transactions (Cambridge, England : 2003) 20110614 |
| Anomalously slow proton transport of a water molecule. | The journal of physical chemistry. B 20110519 |
| The reaction of azoles with 17-chloro-16-formylandrosta-5,16-dien-3β-yl-acetate: synthesis and structural elucidation of novel 16-azolylmethylene-17-oxoandrostanes. | Steroids 20110501 |
| Tuning protein autoinhibition by domain destabilization. | Nature structural & molecular biology 20110501 |
| Scaffold-hopping strategy: synthesis and biological evaluation of 5,6-fused bicyclic heteroaromatics to identify orally bioavailable anticancer agents. | Journal of medicinal chemistry 20110428 |
| Intermolecular vibrational modes and orientational dynamics of cooperative hydrogen-bonding dimer of 7-azaindole in solution. | The Journal of chemical physics 20110428 |
| Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists. | Bioorganic & medicinal chemistry letters 20110415 |
| Photon induced isomerization in the first excited state of the 7-azaindole-(H2O)3 cluster. | Physical chemistry chemical physics : PCCP 20110407 |
| Inhibition of light-induced tautomerization of 7-azaindole by phenol: indications of proton-coupled electron/energy transfer quenching. | The journal of physical chemistry. A 20110317 |
| Targeting BRAFV600E with PLX4720 displays potent antimigratory and anti-invasive activity in preclinical models of human thyroid cancer. | The oncologist 20110301 |
| Strong agostic-type interactions in ruthenium benzylidene complexes containing 7-azaindole based scorpionate ligands. | Dalton transactions (Cambridge, England : 2003) 20110128 |
| Azaindoles as potent CRTH2 receptor antagonists. | Bioorganic & medicinal chemistry letters 20110115 |
| Excited-state double proton transfer of 7-azaindole dimers in a low-temperature organic glass. | Photochemistry and photobiology 20110101 |
| Discovery of new azaindole-based PI3Kα inhibitors: apoptotic and antiangiogenic effect on cancer cells. | Bioorganic & medicinal chemistry letters 20101215 |
| Synthesis of new pyrrolo[2,3-d]pyrimidine derivatives as antibacterial and antifungal agents. | European journal of medicinal chemistry 20101101 |
| Excited-state triple-proton transfer in 7-azaindole(H(2)O)(2) and reaction path studied by electronic spectroscopy in the gas phase and quantum chemical calculations. | The journal of physical chemistry. A 20101028 |
| Recent experimental advances on excited-state intramolecular proton coupled electron transfer reaction. | Accounts of chemical research 20101019 |
| Palladium-catalyzed amination of unprotected halo-7-azaindoles. | Organic letters 20101015 |
| Luminescence and reactivity of 7-azaindole derivatives and complexes. | Chemical Society reviews 20100801 |
| Excited state charge transfer coupled double proton transfer reaction of 7-azaindole derivatives in methanol: a theoretical study. | The journal of physical chemistry. A 20100729 |
| Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626. | Bioorganic & medicinal chemistry 20100715 |
| New insights into homopiperazine-based 5-HT1A/5-HT7R ligands: synthesis and biological evaluation. | Journal of enzyme inhibition and medicinal chemistry 20100601 |
| Activation energy of the two-proton phototautomerism in 7-azaindole dimer and its medium-dependence. | The journal of physical chemistry. A 20100513 |
| New 7-azaindole palladium and platinum complexes: crystal structures and theoretical calculations. In vitro anticancer activity of the platinum compounds. | Dalton transactions (Cambridge, England : 2003) 20100407 |
| Theoretical studies for the rates and kinetic isotope effects of the excited-state double proton transfer in the 1:1 7-azaindole:H2O complex using variational transition state theory including multidimensional tunneling. | The journal of physical chemistry. A 20100318 |
| Infrared spectroscopy of jet-cooled tautomeric dimer of 7-azaindole: a model system for the ground-state double proton transfer reaction. | The journal of physical chemistry. A 20100311 |
| Discovery of 4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamides as selective, orally active inhibitors of protein kinase B (Akt). | Journal of medicinal chemistry 20100311 |
| Proton phototransfers in doubly hydrogen bonded dimers: the photophysics of 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indole dimers. | The journal of physical chemistry. A 20100121 |
| A novel chemotype of kinase inhibitors: Discovery of 3,4-ring fused 7-azaindoles and deazapurines as potent JAK2 inhibitors. | Bioorganic & medicinal chemistry letters 20100101 |
| 3D-QSAR and molecular docking studies on derivatives of MK-0457, GSK1070916 and SNS-314 as inhibitors against Aurora B kinase. | International journal of molecular sciences 20100101 |
| Phosphatidylserine increases IKBKAP levels in familial dysautonomia cells. | PloS one 20100101 |
| Marine pyrrolocarbazoles and analogues: synthesis and kinase inhibition. | Marine drugs 20091201 |
| 2-(3,4,5-Trimethoxy-phen-yl)-1H-pyrrolo[2,3-b]pyridine. | Acta crystallographica. Section E, Structure reports online 20091201 |
| Evolving a polymerase for hydrophobic base analogues. | Journal of the American Chemical Society 20091021 |
| Impact of donor-acceptor geometry and metal chelation on photophysical properties and applications of triarylboranes. | Accounts of chemical research 20091020 |
| Fluorescent analogues of quinoline reveal amine ligand loss from cis and trans platinum(II) complexes in cancer cells. | Journal of inorganic biochemistry 20090801 |
| Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships. | Journal of medicinal chemistry 20090723 |
| Synthesis and cytotoxic activity of 5,6-heteroaromatically annulated pyridine-2,4-diamines. | Bioorganic & medicinal chemistry 20090701 |
| Charge transfer interaction of intermolecular hydrogen bonds in 7-azaindole(MeOH)n (n = 1, 2) with IR-dip spectroscopy and natural bond orbital analysis. | The journal of physical chemistry. A 20090625 |
| Spectroscopic study on the structural isomers of 7-azaindole(ethanol)(n) (n=1-3) and multiple-proton transfer reactions in the gas phase. | The Journal of chemical physics 20090614 |
| A new family of metallaboratrane complexes based on 7-azaindole: B-H activation mediated by carbon monoxide. | Chemical communications (Cambridge, England) 20090514 |
| 4-Phenyl-7-azaindoles as potent and selective IKK2 inhibitors. | Bioorganic & medicinal chemistry letters 20090501 |
| Beyond 7-azaindole: conjugation effects on intermolecular double hydrogen-atom transfer reactions. | The journal of physical chemistry. A 20090430 |
| Theoretical evidence of barrier-free proton transfer in 7-azaindole-water cluster anions. | The Journal of chemical physics 20090428 |
| Structural insights for design of potent spleen tyrosine kinase inhibitors from crystallographic analysis of three inhibitor complexes. | Chemical biology & drug design 20090401 |
| Probe of the NH bond strength in 1L(a) and 1L(b) states of 7-azaindole with IR-dip spectroscopy: insights into the electronic-state dependence of the multiple proton/hydrogen transfers in hydrogen-bonded clusters. | The journal of physical chemistry. A 20090326 |
| Site-selective azaindole arylation at the azine and azole rings via N-oxide activation. | Organic letters 20090319 |
| Cu(I) and Ag(I) complexes of 7-azaindolyl and 2,2'-dipyridylamino substituted 1,3,5-triazine and benzene: the central core impact on structure, solution dynamics and fluorescence of the complexes. | Dalton transactions (Cambridge, England : 2003) 20090314 |
| Mode-selective vibrational redistribution after spectrally selective N-H stretching mode excitation in intermolecular hydrogen bonds. | The Journal of chemical physics 20090121 |
| Cobalt-catalyzed N-arylation of nitrogen nucleophiles in water. | Chemistry (Weinheim an der Bergstrasse, Germany) 20090101 |
| Impact of the linker groups in bis(7-azaindol-1-yl) chelate ligands on structures and stability of Pt(N,N-L)R(2) complexes. | Dalton transactions (Cambridge, England : 2003) 20081228 |
| Synthesis of a 7-azaindole by chichibabin cyclization: reversible base-mediated dimerization of 3-picolines. | The Journal of organic chemistry 20081219 |
| Design and synthesis of potent and selective azaindole-based Rho kinase (ROCK) inhibitors. | ChemMedChem 20081201 |
| Cyano analogues of 7-azaindole: probing excited-state charge-coupled proton transfer reactions in protic solvents. | Chemphyschem : a European journal of chemical physics and physical chemistry 20081024 |
| Ab initio QM/MM molecular dynamics study on the excited-state hydrogen transfer of 7-azaindole in water solution. | The journal of physical chemistry. A 20081009 |
| Highly functionalized 7-azaindoles as selective PPAR gamma modulators. | Bioorganic & medicinal chemistry letters 20080901 |
| Knowledge-based design of 7-azaindoles as selective B-Raf inhibitors. | Bioorganic & medicinal chemistry letters 20080815 |
| Distribution and favorable binding sites of pyrroloquinoline and its analogues in a lipid bilayer studied by molecular dynamics simulations. | Biophysical chemistry 20080801 |
| Electronically excited states of water clusters of 7-azaindole: structures, relative energies, and electronic nature of the excited states. | The Journal of chemical physics 20080607 |
| Rotationally resolved electronic spectroscopy of water clusters of 7-azaindole. | The Journal of chemical physics 20080607 |
| Identification of 4-(4-aminopiperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidines as selective inhibitors of protein kinase B through fragment elaboration. | Journal of medicinal chemistry 20080410 |
| Excited-state double proton transfer in model base pairs: the stepwise reaction on the heterodimer of 7-azaindole analogues. | Chemphyschem : a European journal of chemical physics and physical chemistry 20080201 |
| 7-Azaindole derivatives as potential partial nicotinic agonists. | Bioorganic & medicinal chemistry letters 20080101 |
| Novel 1-(azacyclyl)-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines as 5-HT6 agonists and antagonists. | Bioorganic & medicinal chemistry 20070915 |
| Synthesis and biological activities of isogranulatimide analogues. | Bioorganic & medicinal chemistry 20070901 |
| Laser induced fluorescence spectroscopy of a mixed dimer between 2-pyridone and 7-azaindole. | The journal of physical chemistry. A 20070816 |
| Unraveling the structure of hydrogen bond stretching mode infrared absorption bands: an anharmonic density functional theory study on 7-azaindole dimers. | The Journal of chemical physics 20070807 |
| Cooperative triple-proton/hydrogen atom relay in 7-azaindole(CH3OH)2 in the gas phase: remarkable change in the reaction mechanism from vibrational-mode specific to statistical fashion with increasing internal energy. | The journal of physical chemistry. A 20070531 |
| Rapid evolution of 6-phenylpurine inhibitors of protein kinase B through structure-based design. | Journal of medicinal chemistry 20070517 |
| Synthesis and biological evaluation of 7-azaindole derivatives, synthetic cytokinin analogues. | Bioorganic & medicinal chemistry letters 20070401 |
| Bis-imide granulatimide analogues as potent Checkpoint 1 kinase inhibitors. | European journal of pharmacology 20070112 |
| Synthesis and cross-coupling reactions of 7-azaindoles via a new donor-acceptor cyclopropane. | Organic letters 20060817 |
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| Density functional calculations on the structure, vibrational frequencies and normal modes of 7-Azaindole. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060701 |
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| A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid. | The Journal of organic chemistry 20060512 |
| Synthesis and reactivity of N-heterocycle-B(C6F5)3 complexes. 4. Competition between pyridine- and pyrrole-type substrates toward B(C6F5)3: structure and dynamics of 7-B(C6F5)3-7-azaindole and [7-Azaindolium]+[HOB(C6F5)3]-. | Inorganic chemistry 20060220 |
| Charge-transfer pipi* excited state in the 7-azaindole dimer. A hybrid configuration interactions singles/time-dependent density functional theory description. | The journal of physical chemistry. A 20060126 |
| Novel antitumor and radioprotective sulfonamides containing pyrrolo [2,3-d]pyrimidines. | Arzneimittel-Forschung 20060101 |
| Determination of the excited-state structure of 7-azaindole-water cluster using a Franck-Condon analysis. | The Journal of chemical physics 20051208 |
| Excited-state double proton transfer of 7-azaindole in water nanopools. | The journal of physical chemistry. B 20051103 |
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| The molecular symmetry and electronic spectroscopy of 7-azaindole dimer: its proton-transfer channels. | The Journal of chemical physics 20050915 |
| High resolution electronic spectra of 7-azaindole and its Ar atom van der Waals complex. | The Journal of chemical physics 20050901 |
| Excited-state double-proton transfer in the 7-azaindole dimer in the gas phase. 3. Reaction mechanism studied by picosecond time-resolved REMPI spectroscopy. | The journal of physical chemistry. A 20050623 |
| Study of 7-azaindole in its first four singlet states. | The Journal of chemical physics 20050622 |
| Potent, orally active corticotropin-releasing factor receptor-1 antagonists containing a tricyclic pyrrolopyridine or pyrazolopyridine core. | Journal of medicinal chemistry 20050616 |
| Proton transfer of excited 7-azaindole in reverse-micellar methanol nanopools: even faster than in bulk methanol. | The journal of physical chemistry. B 20050428 |
| Excited-state double-proton transfer in the 7-azaindole dimer in the gas phase. 1. Evidence of complete localization in the lowest excited electronic state of asymmetric isotopomers. | The journal of physical chemistry. A 20050331 |
| Excited-state double-proton transfer in the 7-azaindole dimer in the gas phase. 2. Cooperative nature of double-proton transfer revealed by H/D kinetic isotopic effects. | The journal of physical chemistry. A 20050331 |
| Cu(I) and Zn(II) complexes of 7-azaindole-containing scorpionates: structures, luminescence and fluxionality. | Dalton transactions (Cambridge, England : 2003) 20050207 |
| 7-Azaindolyl- and 2,2'-dipyridylamino-functionalized molecular stars with sixfold symmetry: self-assembly, luminescence, and coordination compounds. | Chemistry (Weinheim an der Bergstrasse, Germany) 20050121 |
| Isotopic induction of the excited-state single-proton transfer in 7-azaindole dimer. | Physical chemistry chemical physics : PCCP 20050107 |
| Ionization-induced proton transfer in model DNA base pairs: a theoretical study of the radical ions of the 7-azaindole dimer. | Chemphyschem : a European journal of chemical physics and physical chemistry 20041210 |
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| Preparation of 4-azaindole and 7-azaindole dimers with a bisalkoxyalkyl spacer in order to preferentially target melatonin MT1 receptors over melatonin MT2 receptors. | European journal of medicinal chemistry 20040601 |
| Three-coordinate organoboron compounds BAr2R (Ar = mesityl, R = 7-azaindolyl- or 2,2'-dipyridylamino-functionalized aryl or thienyl) for electroluminescent devices and supramolecular assembly. | Chemistry (Weinheim an der Bergstrasse, Germany) 20040220 |
| Discovery of 4-benzoyl-1-[(4-methoxy-1H- pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2- (R)-methylpiperazine (BMS-378806): a novel HIV-1 attachment inhibitor that interferes with CD4-gp120 interactions. | Journal of medicinal chemistry 20030925 |
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| Syntheses and antiproliferative activities of 7-azarebeccamycin analogues bearing one 7-azaindole moiety. | Journal of medicinal chemistry 20030213 |
| Rebeccamycin analogues as anti-cancer agents. | European journal of medicinal chemistry 20030201 |
| Carbodiimide-mediated preparation of the tricyclic pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine ring system and its application to the synthesis of the potent antitumoral marine alkaloid variolin B and analog. | The Journal of organic chemistry 20030124 |
| Isomerism of bis(7-azaindolyl)methane. | Organic letters 20021114 |
| Synthesis and fluorescence study of 7-azaindole in DNA oligonucleotides replacing a purine base. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20021001 |
| Synthesis of analogs of L-valacyclovir and determination of their substrate activity for the oligopeptide transporter in Caco-2 cells. | European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20020701 |
| Low temperature luminescence behaviours of 7-azatryptophan, 5-hydroxytryptophan and their chromophoric moieties. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20020701 |
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