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1477-50-5 | 1H-Indole-2-carboxylic acid
CAS No: 1477-50-5 Catalog No: AG001F43 MDL No:MFCD00005611
Product Description
Catalog Number:
AG001F43
Chemical Name:
1H-Indole-2-carboxylic acid
CAS Number:
1477-50-5
Molecular Formula:
C9H7NO2
Molecular Weight:
161.1574
MDL Number:
MFCD00005611
IUPAC Name:
1H-indole-2-carboxylic acid
InChI:
InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)
InChI Key:
HCUARRIEZVDMPT-UHFFFAOYSA-N
SMILES:
OC(=O)c1cc2c([nH]1)cccc2
EC Number:
216-030-4
NSC Number:
16598
Properties
Complexity:
193
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
161.048g/mol
Formal Charge:
0
Heavy Atom Count:
12
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
161.16g/mol
Monoisotopic Mass:
161.048g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
53.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.3
Literature
| Title | Journal |
|---|---|
| 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. | The Journal of organic chemistry 20120817 |
| Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids. | The Journal of organic chemistry 20120803 |
| Photophysics of indole-2-carboxylic acid in an aqueous environment studied by fluorescence spectroscopy in combination with ab initio calculations. | Physical chemistry chemical physics : PCCP 20120214 |
| CSAR benchmark exercise of 2010: combined evaluation across all submitted scoring functions. | Journal of chemical information and modeling 20110926 |
| I. Novel HCV NS5B polymerase inhibitors: discovery of indole 2-carboxylic acids with C3-heterocycles. | Bioorganic & medicinal chemistry letters 20110915 |
| Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma. | Bioorganic & medicinal chemistry letters 20110715 |
| Bis(2,2'-bipyridine-κN,N')bis-(1H-indole-2-carboxyl-ato-κO,O')cadmium-2,2'-bipyridine-water (1/0.5/2). | Acta crystallographica. Section E, Structure reports online 20110701 |
| Kynurenine metabolites and migraine: experimental studies and therapeutic perspectives. | Current neuropharmacology 20110601 |
| Preparation of hippurate-zinc layered hydroxide nanohybrid and its synergistic effect with tamoxifen on HepG2 cell lines. | International journal of nanomedicine 20110101 |
| The discovery and structure-activity relationships of indole-based inhibitors of glutamate carboxypeptidase II. | Bioorganic & medicinal chemistry letters 20101215 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Tunable Pd-catalyzed cyclization of indole-2-carboxylic acid allenamides: carboamination vs microwave-assisted hydroamination. | The Journal of organic chemistry 20101015 |
| Regioselective oxidation of indole- and quinolinecarboxylic acids by cytochrome P450 CYP199A2. | Applied microbiology and biotechnology 20100201 |
| Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process. | Chemical communications (Cambridge, England) 20091228 |
| Catalytic direct acetoxylation of indoles. | The Journal of organic chemistry 20090918 |
| Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies. | Bioorganic & medicinal chemistry 20090715 |
| Functional expression of Francisella tularensis FabH and FabI, potential antibacterial targets. | Protein expression and purification 20090501 |
| Vibrational spectroscopic studies of indolecarboxylic acids and their metal complexes part VIII. 5-methoxyindole-2-carboxylic acid and its Zn(II) complex. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20090301 |
| Aqua-bis(2,2'-bipyridine-κN,N')(1H-indole-2-carboxyl-ato-κO)nickel(II) 1H-indole-2-carboxyl-ate dihydrate. | Acta crystallographica. Section E, Structure reports online 20090101 |
| The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors. | Bioorganic & medicinal chemistry letters 20080601 |
| Effect of dimerization on vibrational spectra of eumelanin precursors. | Photochemistry and photobiology 20080101 |
| Species-specific, P450- and sulfotransferase-mediated novel ring contraction of a naphthyridine-N-oxide compound in cynomolgus monkey. | Chemical research in toxicology 20071101 |
| SmI(2)-promoted radical addition reactions with N-(2-Indolylacyl)oxazolidinones: synthesis of bisindole compounds. | The Journal of organic chemistry 20070525 |
| Selective Modulators of PPAR-gamma Activity: Molecular Aspects Related to Obesity and Side-Effects. | PPAR research 20070101 |
| In vitro scavenging activity for reactive oxygen species by N-substituted indole-2-carboxylic acid esters. | Luminescence : the journal of biological and chemical luminescence 20070101 |
| Characterization of a human coagulation factor Xa-binding site on Viperidae snake venom phospholipases A2 by affinity binding studies and molecular bioinformatics. | BMC structural biology 20070101 |
| Spectral and thermal studies of divalent transition metal with indole-2-carboxylic acid and 4-substituted hydrazinethiocarbamide. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060901 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Spectral and thermal studies of divalent transition metal complexes with indole-2-carboxylic acid and 4-substituted hydrazinethiocarbamide. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060201 |
| Tricyclic quinoxalinediones, aza-kynurenic acids, and indole-2-carboxylic acids as in vivo active NMDA-glycine antagonists. | Current topics in medicinal chemistry 20060101 |
| Cyclization of free radicals at the C-7 position of ethyl indole-2-carboxylate derivatives: an entry to a new class of Duocarmycin Analogues. | Molecules (Basel, Switzerland) 20051231 |
| Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARgamma partial agonists. | Bioorganic & medicinal chemistry letters 20051115 |
| Synthesis and SAR of 2-carboxylic acid indoles as inhibitors of plasminogen activator inhibitor-1. | Bioorganic & medicinal chemistry letters 20050801 |
| 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 of medicinal chemistry 20050714 |
| New synthetic method for indole-2-carboxylate and its application to the total synthesis of duocarmycin SA. | Organic letters 20040819 |
| Factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of neutral P1 substituents. | Bioorganic & medicinal chemistry letters 20040816 |
| Novel factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of P4 substituents in combination with a neutral P1 ligand. | Bioorganic & medicinal chemistry letters 20040816 |
| Discovery and SAR of indole-2-carboxylic acid benzylidene-hydrazides as a new series of potent apoptosis inducers using a cell-based HTS assay. | Bioorganic & medicinal chemistry 20040701 |
| Pacemaker activity in hydra is modulated by glycine receptor ligands. | Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20040601 |
| Non-peptidic small-molecule inhibitors of the single-chain hepatitis C virus NS3 protease/NS4A cofactor complex discovered by structure-based NMR screening. | Journal of medicinal chemistry 20040506 |
| 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. | European journal of medicinal chemistry 20031001 |
| Key substrate recognition residues in the active site of a plant cytochrome P450, CYP73A1. Homology guided site-directed mutagenesis. | European journal of biochemistry 20030901 |
| Tricyclic indole-2-carboxylic acids: highly in vivo active and selective antagonists for the glycine binding site of the NMDA receptor. | Journal of medicinal chemistry 20030227 |
| In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives. | General physiology and biophysics 20020601 |
| Cooperative binding interactions of glycopeptide antibiotics. | Journal of the American Chemical Society 20020417 |
| Physicochemical study of the solid forms of a new drug. | Journal of pharmaceutical sciences 20011201 |
| Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists. | Farmaco (Societa chimica italiana : 1989) 20011001 |
| Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors. | European journal of medicinal chemistry 20010901 |
| Synthesis of tricyclic indole-2-carboxylic [correction of caboxylic] acids as potent NMDA-glycine antagonists. | The Journal of organic chemistry 20010518 |
| Heterocyclic substituted anthralin derivatives as inhibitors of keratinocyte growth and inducers of differentiation. | Bioorganic & medicinal chemistry letters 20010108 |
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