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271-63-6,MFCD00005606
Catalog No.:AA0034B1

271-63-6 | 7-Azaindole

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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA0034B1
Chemical Name:
7-Azaindole
CAS Number:
271-63-6
Molecular Formula:
C7H6N2
Molecular Weight:
118.1359
MDL Number:
MFCD00005606
SMILES:
c1cnc2c(c1)cc[nH]2
Properties
Properties
 
BP:
273.8°C at 760 mmHg  
Form:
Solid  
MP:
105-107 °C(lit.)  
Refractive Index:
1.5500 (estimate)  
Storage:
Keep in dry area;Room Temperature;  

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

Literature

Title: The acid-catalysed synthesis of 7-azaindoles from 3-alkynyl-2-aminopyridines and their antimicrobial activity.

Journal: Organic & biomolecular chemistry 20140114

Title: Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction.

Journal: Organic & biomolecular chemistry 20121128

Title: Theoretical study on water-mediated excited-state multiple proton transfer in 7-azaindole: significance of hydrogen bond rearrangement.

Journal: The journal of physical chemistry. A 20121101

Title: Excited state tautomerization of 7-azaindole in a 1:1 complex with δ-valerolactam: a comparative study with the homodimer.

Journal: The journal of physical chemistry. A 20121011

Title: How to modify 7-azaindole to form cytotoxic Pt(II) complexes: highly in vitro anticancer effective cisplatin derivatives involving halogeno-substituted 7-azaindole.

Journal: Journal of inorganic biochemistry 20121001

Title: 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.

Journal: Acta crystallographica. Section E, Structure reports online 20121001

Title: Theoretical study of the excited-state double proton transfer in the (3-methyl-7-azaindole)-(7-azaindole) heterodimer.

Journal: Journal of computational chemistry 20120730

Title: Design, synthesis, and evaluation of 3,5-disubstituted 7-azaindoles as Trk inhibitors with anticancer and antiangiogenic activities.

Journal: Journal of medicinal chemistry 20120614

Title: Novel pyrazole derivatives as anticancer and radiosensitizing agents.

Journal: Arzneimittel-Forschung 20120301

Title: Synthesis and antibacterial activity against ralstonia solanacearum for novel hydrazone derivatives containing a pyridine moiety.

Journal: Chemistry Central journal 20120101

Title: Solvent effects in the excited-state tautomerization of 7-azaindole: a theoretical study.

Journal: The journal of physical chemistry. B 20111222

Title: Discovery and optimization of indoles and 7-azaindoles as Rho kinase (ROCK) inhibitors (part-I).

Journal: Bioorganic & medicinal chemistry letters 20111201

Title: Theoretical studies for excited-state tautomerization in the 7-azaindole-(CH3OH)n (n = 1 and 2) complexes in the gas phase.

Journal: The journal of physical chemistry. A 20111201

Title: Discovery and optimization of indole and 7-azaindoles as Rho kinase (ROCK) inhibitors (part-II).

Journal: Bioorganic & medicinal chemistry letters 20111201

Title: Direct functionalization of (un)protected tetrahydroisoquinoline and isochroman under iron and copper catalysis: two metals, two mechanisms.

Journal: The Journal of organic chemistry 20111104

Title: Structure of 7-azaindole···2-fluoropyridine dimer in a supersonic jet: competition between N-H···N and N-H···F interactions.

Journal: The journal of physical chemistry. A 20110922

Title: Structure-based design and optimization of potent renin inhibitors on 5- or 7-azaindole-scaffolds.

Journal: Bioorganic & medicinal chemistry letters 20110915

Title: Excited state electron transfer precedes proton transfer following irradiation of the hydrogen-bonded single water complex of 7-azaindole with UV light.

Journal: The Journal of chemical physics 20110828

Title: From insertion of rhodium acetate paddlewheels into functionalized 7-azaindole hydrogen-bonded dimers to infinite architectures.

Journal: Dalton transactions (Cambridge, England : 2003) 20110728

Title: Selectivity of kinase inhibitor fragments.

Journal: Journal of medicinal chemistry 20110728

Title: 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.

Journal: Physical chemistry chemical physics : PCCP 20110621

Title: Synthesis and characterisation of group nine transition metal complexes containing new mesityl and naphthyl based azaindole scorpionate ligands.

Journal: Dalton transactions (Cambridge, England : 2003) 20110614

Title: Anomalously slow proton transport of a water molecule.

Journal: The journal of physical chemistry. B 20110519

Title: 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.

Journal: Steroids 20110501

Title: Tuning protein autoinhibition by domain destabilization.

Journal: Nature structural & molecular biology 20110501

Title: Scaffold-hopping strategy: synthesis and biological evaluation of 5,6-fused bicyclic heteroaromatics to identify orally bioavailable anticancer agents.

Journal: Journal of medicinal chemistry 20110428

Title: Intermolecular vibrational modes and orientational dynamics of cooperative hydrogen-bonding dimer of 7-azaindole in solution.

Journal: The Journal of chemical physics 20110428

Title: Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists.

Journal: Bioorganic & medicinal chemistry letters 20110415

Title: Photon induced isomerization in the first excited state of the 7-azaindole-(H2O)3 cluster.

Journal: Physical chemistry chemical physics : PCCP 20110407

Title: Inhibition of light-induced tautomerization of 7-azaindole by phenol: indications of proton-coupled electron/energy transfer quenching.

Journal: The journal of physical chemistry. A 20110317

Title: Targeting BRAFV600E with PLX4720 displays potent antimigratory and anti-invasive activity in preclinical models of human thyroid cancer.

Journal: The oncologist 20110301

Title: Strong agostic-type interactions in ruthenium benzylidene complexes containing 7-azaindole based scorpionate ligands.

Journal: Dalton transactions (Cambridge, England : 2003) 20110128

Title: Azaindoles as potent CRTH2 receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 20110115

Title: Excited-state double proton transfer of 7-azaindole dimers in a low-temperature organic glass.

Journal: Photochemistry and photobiology 20110101

Title: Discovery of new azaindole-based PI3Kα inhibitors: apoptotic and antiangiogenic effect on cancer cells.

Journal: Bioorganic & medicinal chemistry letters 20101215

Title: Synthesis of new pyrrolo[2,3-d]pyrimidine derivatives as antibacterial and antifungal agents.

Journal: European journal of medicinal chemistry 20101101

Title: 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.

Journal: The journal of physical chemistry. A 20101028

Title: Recent experimental advances on excited-state intramolecular proton coupled electron transfer reaction.

Journal: Accounts of chemical research 20101019

Title: Palladium-catalyzed amination of unprotected halo-7-azaindoles.

Journal: Organic letters 20101015

Title: Luminescence and reactivity of 7-azaindole derivatives and complexes.

Journal: Chemical Society reviews 20100801

Title: Excited state charge transfer coupled double proton transfer reaction of 7-azaindole derivatives in methanol: a theoretical study.

Journal: The journal of physical chemistry. A 20100729

Title: Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626.

Journal: Bioorganic & medicinal chemistry 20100715

Title: New insights into homopiperazine-based 5-HT1A/5-HT7R ligands: synthesis and biological evaluation.

Journal: Journal of enzyme inhibition and medicinal chemistry 20100601

Title: Activation energy of the two-proton phototautomerism in 7-azaindole dimer and its medium-dependence.

Journal: The journal of physical chemistry. A 20100513

Title: New 7-azaindole palladium and platinum complexes: crystal structures and theoretical calculations. In vitro anticancer activity of the platinum compounds.

Journal: Dalton transactions (Cambridge, England : 2003) 20100407

Title: 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.

Journal: The journal of physical chemistry. A 20100318

Title: Infrared spectroscopy of jet-cooled tautomeric dimer of 7-azaindole: a model system for the ground-state double proton transfer reaction.

Journal: The journal of physical chemistry. A 20100311

Title: 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: Journal of medicinal chemistry 20100311

Title: Proton phototransfers in doubly hydrogen bonded dimers: the photophysics of 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indole dimers.

Journal: The journal of physical chemistry. A 20100121

Title: A novel chemotype of kinase inhibitors: Discovery of 3,4-ring fused 7-azaindoles and deazapurines as potent JAK2 inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20100101

Title: 3D-QSAR and molecular docking studies on derivatives of MK-0457, GSK1070916 and SNS-314 as inhibitors against Aurora B kinase.

Journal: International journal of molecular sciences 20100101

Title: Phosphatidylserine increases IKBKAP levels in familial dysautonomia cells.

Journal: PloS one 20100101

Title: Marine pyrrolocarbazoles and analogues: synthesis and kinase inhibition.

Journal: Marine drugs 20091201

Title: 2-(3,4,5-Trimethoxy-phen-yl)-1H-pyrrolo[2,3-b]pyridine.

Journal: Acta crystallographica. Section E, Structure reports online 20091201

Title: Evolving a polymerase for hydrophobic base analogues.

Journal: Journal of the American Chemical Society 20091021

Title: Impact of donor-acceptor geometry and metal chelation on photophysical properties and applications of triarylboranes.

Journal: Accounts of chemical research 20091020

Title: Fluorescent analogues of quinoline reveal amine ligand loss from cis and trans platinum(II) complexes in cancer cells.

Journal: Journal of inorganic biochemistry 20090801

Title: Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships.

Journal: Journal of medicinal chemistry 20090723

Title: Synthesis and cytotoxic activity of 5,6-heteroaromatically annulated pyridine-2,4-diamines.

Journal: Bioorganic & medicinal chemistry 20090701

Title: Charge transfer interaction of intermolecular hydrogen bonds in 7-azaindole(MeOH)n (n = 1, 2) with IR-dip spectroscopy and natural bond orbital analysis.

Journal: The journal of physical chemistry. A 20090625

Title: Spectroscopic study on the structural isomers of 7-azaindole(ethanol)(n) (n=1-3) and multiple-proton transfer reactions in the gas phase.

Journal: The Journal of chemical physics 20090614

Title: A new family of metallaboratrane complexes based on 7-azaindole: B-H activation mediated by carbon monoxide.

Journal: Chemical communications (Cambridge, England) 20090514

Title: 4-Phenyl-7-azaindoles as potent and selective IKK2 inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20090501

Title: Beyond 7-azaindole: conjugation effects on intermolecular double hydrogen-atom transfer reactions.

Journal: The journal of physical chemistry. A 20090430

Title: Theoretical evidence of barrier-free proton transfer in 7-azaindole-water cluster anions.

Journal: The Journal of chemical physics 20090428

Title: Structural insights for design of potent spleen tyrosine kinase inhibitors from crystallographic analysis of three inhibitor complexes.

Journal: Chemical biology & drug design 20090401

Title: 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.

Journal: The journal of physical chemistry. A 20090326

Title: Site-selective azaindole arylation at the azine and azole rings via N-oxide activation.

Journal: Organic letters 20090319

Title: 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.

Journal: Dalton transactions (Cambridge, England : 2003) 20090314

Title: Mode-selective vibrational redistribution after spectrally selective N-H stretching mode excitation in intermolecular hydrogen bonds.

Journal: The Journal of chemical physics 20090121

Title: Cobalt-catalyzed N-arylation of nitrogen nucleophiles in water.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20090101

Title: 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.

Journal: Dalton transactions (Cambridge, England : 2003) 20081228

Title: Synthesis of a 7-azaindole by chichibabin cyclization: reversible base-mediated dimerization of 3-picolines.

Journal: The Journal of organic chemistry 20081219

Title: Design and synthesis of potent and selective azaindole-based Rho kinase (ROCK) inhibitors.

Journal: ChemMedChem 20081201

Title: Cyano analogues of 7-azaindole: probing excited-state charge-coupled proton transfer reactions in protic solvents.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20081024

Title: Ab initio QM/MM molecular dynamics study on the excited-state hydrogen transfer of 7-azaindole in water solution.

Journal: The journal of physical chemistry. A 20081009

Title: Highly functionalized 7-azaindoles as selective PPAR gamma modulators.

Journal: Bioorganic & medicinal chemistry letters 20080901

Title: Knowledge-based design of 7-azaindoles as selective B-Raf inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20080815

Title: Distribution and favorable binding sites of pyrroloquinoline and its analogues in a lipid bilayer studied by molecular dynamics simulations.

Journal: Biophysical chemistry 20080801

Title: Electronically excited states of water clusters of 7-azaindole: structures, relative energies, and electronic nature of the excited states.

Journal: The Journal of chemical physics 20080607

Title: Rotationally resolved electronic spectroscopy of water clusters of 7-azaindole.

Journal: The Journal of chemical physics 20080607

Title: Identification of 4-(4-aminopiperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidines as selective inhibitors of protein kinase B through fragment elaboration.

Journal: Journal of medicinal chemistry 20080410

Title: Excited-state double proton transfer in model base pairs: the stepwise reaction on the heterodimer of 7-azaindole analogues.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20080201

Title: 7-Azaindole derivatives as potential partial nicotinic agonists.

Journal: Bioorganic & medicinal chemistry letters 20080101

Title: Novel 1-(azacyclyl)-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines as 5-HT6 agonists and antagonists.

Journal: Bioorganic & medicinal chemistry 20070915

Title: Synthesis and biological activities of isogranulatimide analogues.

Journal: Bioorganic & medicinal chemistry 20070901

Title: Laser induced fluorescence spectroscopy of a mixed dimer between 2-pyridone and 7-azaindole.

Journal: The journal of physical chemistry. A 20070816

Title: Unraveling the structure of hydrogen bond stretching mode infrared absorption bands: an anharmonic density functional theory study on 7-azaindole dimers.

Journal: The Journal of chemical physics 20070807

Title: 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.

Journal: The journal of physical chemistry. A 20070531

Title: Rapid evolution of 6-phenylpurine inhibitors of protein kinase B through structure-based design.

Journal: Journal of medicinal chemistry 20070517

Title: Synthesis and biological evaluation of 7-azaindole derivatives, synthetic cytokinin analogues.

Journal: Bioorganic & medicinal chemistry letters 20070401

Title: Bis-imide granulatimide analogues as potent Checkpoint 1 kinase inhibitors.

Journal: European journal of pharmacology 20070112

Title: Synthesis and cross-coupling reactions of 7-azaindoles via a new donor-acceptor cyclopropane.

Journal: Organic letters 20060817

Title: Excited state proton transfer in 3-methyl-7-azaindole dimer. Symmetry control.

Journal: The journal of physical chemistry. A 20060727

Title: Density functional calculations on the structure, vibrational frequencies and normal modes of 7-Azaindole.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060701

Title: 3-(4-Piperidinyl)indoles and 3-(4-piperidinyl)pyrrolo-[2,3-b]pyridines as ligands for the ORL-1 receptor.

Journal: Bioorganic & medicinal chemistry letters 20060701

Title: A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid.

Journal: The Journal of organic chemistry 20060512

Title: 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]-.

Journal: Inorganic chemistry 20060220

Title: Charge-transfer pipi* excited state in the 7-azaindole dimer. A hybrid configuration interactions singles/time-dependent density functional theory description.

Journal: The journal of physical chemistry. A 20060126

Title: Novel antitumor and radioprotective sulfonamides containing pyrrolo [2,3-d]pyrimidines.

Journal: Arzneimittel-Forschung 20060101

Title: Determination of the excited-state structure of 7-azaindole-water cluster using a Franck-Condon analysis.

Journal: The Journal of chemical physics 20051208

Title: Excited-state double proton transfer of 7-azaindole in water nanopools.

Journal: The journal of physical chemistry. B 20051103

Title: Synthesis and cytotoxicities of 7-aza rebeccamycin analogues bearing various substituents on the sugar moiety, on the imide nitrogen and on the carbazole framework.

Journal: European journal of medicinal chemistry 20051001

Title: The molecular symmetry and electronic spectroscopy of 7-azaindole dimer: its proton-transfer channels.

Journal: The Journal of chemical physics 20050915

Title: High resolution electronic spectra of 7-azaindole and its Ar atom van der Waals complex.

Journal: The Journal of chemical physics 20050901

Title: Excited-state double-proton transfer in the 7-azaindole dimer in the gas phase. 3. Reaction mechanism studied by picosecond time-resolved REMPI spectroscopy.

Journal: The journal of physical chemistry. A 20050623

Title: Study of 7-azaindole in its first four singlet states.

Journal: The Journal of chemical physics 20050622

Title: Potent, orally active corticotropin-releasing factor receptor-1 antagonists containing a tricyclic pyrrolopyridine or pyrazolopyridine core.

Journal: Journal of medicinal chemistry 20050616

Title: Proton transfer of excited 7-azaindole in reverse-micellar methanol nanopools: even faster than in bulk methanol.

Journal: The journal of physical chemistry. B 20050428

Title: 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.

Journal: The journal of physical chemistry. A 20050331

Title: 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.

Journal: The journal of physical chemistry. A 20050331

Title: Cu(I) and Zn(II) complexes of 7-azaindole-containing scorpionates: structures, luminescence and fluxionality.

Journal: Dalton transactions (Cambridge, England : 2003) 20050207

Title: 7-Azaindolyl- and 2,2'-dipyridylamino-functionalized molecular stars with sixfold symmetry: self-assembly, luminescence, and coordination compounds.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20050121

Title: Isotopic induction of the excited-state single-proton transfer in 7-azaindole dimer.

Journal: Physical chemistry chemical physics : PCCP 20050107

Title: Ionization-induced proton transfer in model DNA base pairs: a theoretical study of the radical ions of the 7-azaindole dimer.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20041210

Title: Synthesis and evaluation of fluorine-substituted 1H-pyrrolo[2,3-b]pyridine derivatives for dopamine D4 receptor imaging.

Journal: Bioorganic & medicinal chemistry 20041101

Title: Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis.

Journal: Journal of medicinal chemistry 20040603

Title: Preparation of 4-azaindole and 7-azaindole dimers with a bisalkoxyalkyl spacer in order to preferentially target melatonin MT1 receptors over melatonin MT2 receptors.

Journal: European journal of medicinal chemistry 20040601

Title: Three-coordinate organoboron compounds BAr2R (Ar = mesityl, R = 7-azaindolyl- or 2,2'-dipyridylamino-functionalized aryl or thienyl) for electroluminescent devices and supramolecular assembly.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20040220

Title: 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: Journal of medicinal chemistry 20030925

Title: Efficient biosynthetic incorporation of tryptophan and indole analogs in an integral membrane protein.

Journal: Protein science : a publication of the Protein Society 20030901

Title: Blue luminescent rigid molecular rods bearing N-7-azaindolyl and 2,2'-dipyridylamino and their Zn(II) and Ag(I) complexes.

Journal: Inorganic chemistry 20030421

Title: Syntheses and antiproliferative activities of rebeccamycin analogues bearing two 7-azaindole moieties.

Journal: Bioorganic & medicinal chemistry 20030306

Title: Syntheses and antiproliferative activities of 7-azarebeccamycin analogues bearing one 7-azaindole moiety.

Journal: Journal of medicinal chemistry 20030213

Title: Rebeccamycin analogues as anti-cancer agents.

Journal: European journal of medicinal chemistry 20030201

Title: 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.

Journal: The Journal of organic chemistry 20030124

Title: Isomerism of bis(7-azaindolyl)methane.

Journal: Organic letters 20021114

Title: Synthesis and fluorescence study of 7-azaindole in DNA oligonucleotides replacing a purine base.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20021001

Title: Synthesis of analogs of L-valacyclovir and determination of their substrate activity for the oligopeptide transporter in Caco-2 cells.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20020701

Title: Low temperature luminescence behaviours of 7-azatryptophan, 5-hydroxytryptophan and their chromophoric moieties.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20020701

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Tags:271-63-6 Molecular Formula|271-63-6 MDL|271-63-6 SMILES|271-63-6 7-Azaindole