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1477-50-5,MFCD00005611
Catalog No.:AA001F1B

1477-50-5 | Indole-2-carboxylic acid

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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001F1B
Chemical Name:
Indole-2-carboxylic acid
CAS Number:
1477-50-5
Molecular Formula:
C9H7NO2
Molecular Weight:
161.1574
MDL Number:
MFCD00005611
SMILES:
OC(=O)c1cc2c([nH]1)cccc2
NSC Number:
16598
Properties
Properties
 
BP:
419.6°C at 760 mmHg  
Form:
Solid  
MP:
202-206 °C(lit.);  
Refractive Index:
1.5050 (estimate)  
Solubility:
Soluble in clear yellow solution 5% in ethanol, dimethyl sulfoxide and methanol.  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
193  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
2.3  

Literature

Title: Palladium-catalyzed annulation of allenes with indole-2-carboxylic acid derivatives: synthesis of indolo[2,3-c]pyrane-1-ones via Ar-I reactivity or C-H functionalization.

Journal: The Journal of organic chemistry 20120817

Title: Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids.

Journal: The Journal of organic chemistry 20120803

Title: Photophysics of indole-2-carboxylic acid in an aqueous environment studied by fluorescence spectroscopy in combination with ab initio calculations.

Journal: Physical chemistry chemical physics : PCCP 20120214

Title: CSAR benchmark exercise of 2010: combined evaluation across all submitted scoring functions.

Journal: Journal of chemical information and modeling 20110926

Title: I. Novel HCV NS5B polymerase inhibitors: discovery of indole 2-carboxylic acids with C3-heterocycles.

Journal: Bioorganic & medicinal chemistry letters 20110915

Title: Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma.

Journal: Bioorganic & medicinal chemistry letters 20110715

Title: Bis(2,2'-bipyridine-κN,N')bis-(1H-indole-2-carboxyl-ato-κO,O')cadmium-2,2'-bipyridine-water (1/0.5/2).

Journal: Acta crystallographica. Section E, Structure reports online 20110701

Title: Kynurenine metabolites and migraine: experimental studies and therapeutic perspectives.

Journal: Current neuropharmacology 20110601

Title: Preparation of hippurate-zinc layered hydroxide nanohybrid and its synergistic effect with tamoxifen on HepG2 cell lines.

Journal: International journal of nanomedicine 20110101

Title: The discovery and structure-activity relationships of indole-based inhibitors of glutamate carboxypeptidase II.

Journal: Bioorganic & medicinal chemistry letters 20101215

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Tunable Pd-catalyzed cyclization of indole-2-carboxylic acid allenamides: carboamination vs microwave-assisted hydroamination.

Journal: The Journal of organic chemistry 20101015

Title: Regioselective oxidation of indole- and quinolinecarboxylic acids by cytochrome P450 CYP199A2.

Journal: Applied microbiology and biotechnology 20100201

Title: Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process.

Journal: Chemical communications (Cambridge, England) 20091228

Title: Catalytic direct acetoxylation of indoles.

Journal: The Journal of organic chemistry 20090918

Title: Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.

Journal: Bioorganic & medicinal chemistry 20090715

Title: Functional expression of Francisella tularensis FabH and FabI, potential antibacterial targets.

Journal: Protein expression and purification 20090501

Title: Vibrational spectroscopic studies of indolecarboxylic acids and their metal complexes part VIII. 5-methoxyindole-2-carboxylic acid and its Zn(II) complex.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20090301

Title: Aqua-bis(2,2'-bipyridine-κN,N')(1H-indole-2-carboxyl-ato-κO)nickel(II) 1H-indole-2-carboxyl-ate dihydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20090101

Title: The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20080601

Title: Effect of dimerization on vibrational spectra of eumelanin precursors.

Journal: Photochemistry and photobiology 20080101

Title: Species-specific, P450- and sulfotransferase-mediated novel ring contraction of a naphthyridine-N-oxide compound in cynomolgus monkey.

Journal: Chemical research in toxicology 20071101

Title: SmI(2)-promoted radical addition reactions with N-(2-Indolylacyl)oxazolidinones: synthesis of bisindole compounds.

Journal: The Journal of organic chemistry 20070525

Title: Selective Modulators of PPAR-gamma Activity: Molecular Aspects Related to Obesity and Side-Effects.

Journal: PPAR research 20070101

Title: In vitro scavenging activity for reactive oxygen species by N-substituted indole-2-carboxylic acid esters.

Journal: Luminescence : the journal of biological and chemical luminescence 20070101

Title: Characterization of a human coagulation factor Xa-binding site on Viperidae snake venom phospholipases A2 by affinity binding studies and molecular bioinformatics.

Journal: BMC structural biology 20070101

Title: Spectral and thermal studies of divalent transition metal with indole-2-carboxylic acid and 4-substituted hydrazinethiocarbamide.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060901

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Spectral and thermal studies of divalent transition metal complexes with indole-2-carboxylic acid and 4-substituted hydrazinethiocarbamide.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060201

Title: Tricyclic quinoxalinediones, aza-kynurenic acids, and indole-2-carboxylic acids as in vivo active NMDA-glycine antagonists.

Journal: Current topics in medicinal chemistry 20060101

Title: Cyclization of free radicals at the C-7 position of ethyl indole-2-carboxylate derivatives: an entry to a new class of Duocarmycin Analogues.

Journal: Molecules (Basel, Switzerland) 20051231

Title: Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARgamma partial agonists.

Journal: Bioorganic & medicinal chemistry letters 20051115

Title: Synthesis and SAR of 2-carboxylic acid indoles as inhibitors of plasminogen activator inhibitor-1.

Journal: Bioorganic & medicinal chemistry letters 20050801

Title: Probing the subpockets of factor Xa reveals two binding modes for inhibitors based on a 2-carboxyindole scaffold: a study combining structure-activity relationship and X-ray crystallography.

Journal: Journal of medicinal chemistry 20050714

Title: New synthetic method for indole-2-carboxylate and its application to the total synthesis of duocarmycin SA.

Journal: Organic letters 20040819

Title: Factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of neutral P1 substituents.

Journal: Bioorganic & medicinal chemistry letters 20040816

Title: Novel factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of P4 substituents in combination with a neutral P1 ligand.

Journal: Bioorganic & medicinal chemistry letters 20040816

Title: Discovery and SAR of indole-2-carboxylic acid benzylidene-hydrazides as a new series of potent apoptosis inducers using a cell-based HTS assay.

Journal: Bioorganic & medicinal chemistry 20040701

Title: Pacemaker activity in hydra is modulated by glycine receptor ligands.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20040601

Title: Non-peptidic small-molecule inhibitors of the single-chain hepatitis C virus NS3 protease/NS4A cofactor complex discovered by structure-based NMR screening.

Journal: Journal of medicinal chemistry 20040506

Title: Variations of acidic functions at position 2 and substituents at positions 4, 5 and 6 of the indole moiety and their effect on NMDA-glycine site affinity.

Journal: European journal of medicinal chemistry 20031001

Title: Key substrate recognition residues in the active site of a plant cytochrome P450, CYP73A1. Homology guided site-directed mutagenesis.

Journal: European journal of biochemistry 20030901

Title: Tricyclic indole-2-carboxylic acids: highly in vivo active and selective antagonists for the glycine binding site of the NMDA receptor.

Journal: Journal of medicinal chemistry 20030227

Title: In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives.

Journal: General physiology and biophysics 20020601

Title: Cooperative binding interactions of glycopeptide antibiotics.

Journal: Journal of the American Chemical Society 20020417

Title: Physicochemical study of the solid forms of a new drug.

Journal: Journal of pharmaceutical sciences 20011201

Title: Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists.

Journal: Farmaco (Societa chimica italiana : 1989) 20011001

Title: Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors.

Journal: European journal of medicinal chemistry 20010901

Title: Synthesis of tricyclic indole-2-carboxylic [correction of caboxylic] acids as potent NMDA-glycine antagonists.

Journal: The Journal of organic chemistry 20010518

Title: Heterocyclic substituted anthralin derivatives as inhibitors of keratinocyte growth and inducers of differentiation.

Journal: Bioorganic & medicinal chemistry letters 20010108

Title: 2-Indolecarboxylic acid.

Title: J E Huettner, et al. Indole-2-carboxylic Acid: A Competitive Antagonist of Potentiation by Glycine at the NMDA Receptor. Science. 1989 Mar 24;243(4898):1611-3.

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