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Merck

I5109

Sigma-Aldrich

Indole-2-carboxylic acid

98%

Sinónimos:

2-Carboxyindole, 2-Indolylformic acid, NSC 16598

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About This Item

Fórmula empírica (notación de Hill):
C9H7NO2
Número de CAS:
Peso molecular:
161.16
Beilstein/REAXYS Number:
124132
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

202-206 °C (lit.)

SMILES string

OC(=O)c1cc2ccccc2[nH]1

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

Gene Information

human ... SRD5A1(6715)
rat ... Grin2a(24409)

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Application

  • Reactant for total synthesis of (±)-dibromophakellin and analogs
  • Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine
  • Reactant for stereoselective preparation of renieramycin G analogs
  • Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization
  • Reactant for Pd-catalyzed cyclization
  • Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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R Di Fabio et al.
Journal of medicinal chemistry, 42(18), 3486-3493 (1999-09-10)
A series of analogues of the indole-2-carboxylate GV150526, currently in clinical trials as a potential neuroprotective agent for the control of the cerebral damage after stroke onset, was designed based on previous studies dealing with the electronic features of the
Gopinadhan N Anilkumar et al.
Bioorganic & medicinal chemistry letters, 21(18), 5336-5341 (2011-08-16)
SAR development of indole-based palm site inhibitors of HCV NS5B polymerase exemplified by initial indole lead 1 (NS5B IC(50)=0.9 μM, replicon EC(50)>100 μM) is described. Structure-based drug design led to the incorporation of novel heterocyclic moieties at the indole C3-position
Hideyuki Shiozawa et al.
Journal of the American Chemical Society, 124(15), 3914-3919 (2002-04-11)
Glycopeptide antibiotics of the vancomycin group bind to bacterial cell wall analogue precursors, and typically also form dimers. We have studied the interplay between these two sets of noncovalent bonds formed at separate interfaces. Indole-2-carboxylic acid (L) forms a set
R Rama Suresh et al.
The Journal of organic chemistry, 77(16), 6959-6969 (2012-07-26)
Two methodologies, one involving Ar-I reactivity and the other through C-H functionalization, for the formation of indolo[2,3-c]pyrane-1-ones via the corresponding allenes, are presented. A highly efficient approach to indolo[2,3-c]pyrane-1-one derivatives through the Pd-catalyzed regioselective annulation of allenes with 3-iodo-1-alkylindole-2-carboxylic acids
C Kuehm-Caubere et al.
Journal of medicinal chemistry, 40(8), 1201-1210 (1997-04-11)
Series of indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives were synthesized and evaluated in order to determine the necessary structural requirements for a high inhibition of human LDL copper-induced peroxidation. Various modulations were systematically performed on the indole and cycloalkeno[1,2-b]indole nuclei as well

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