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Key Documents

N17602

Sigma-Aldrich

5-Nitroindole

98%

Synonym(s):

NSC 520594

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About This Item

Empirical Formula (Hill Notation):
C8H6N2O2
CAS Number:
Molecular Weight:
162.15
Beilstein:
383777
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

powder

mp

140-142 °C (lit.)

SMILES string

[O-][N+](=O)c1ccc2[nH]ccc2c1

InChI

1S/C8H6N2O2/c11-10(12)7-1-2-8-6(5-7)3-4-9-8/h1-5,9H

InChI key

OZFPSOBLQZPIAV-UHFFFAOYSA-N

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Application

Reactant for preparation of:
  • Pharmaceutically active 2-oxo-1-pyrrolidine analogues
  • Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Protein Kinase Inhibitors and antiproliferative agents
  • Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)
  • Antifungal agents
  • Cannabinoid receptor type 1 (CB1) antagonists
  • Potential anticancer agents
  • Potential antivascular agents
  • Selective Anti-leukemic agents
  • Anti human immunodeficiency virus subtype 1 (HIV-1) agents

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Wengen Ouyang et al.
Journal of chemical theory and computation, 16(1), 666-676 (2019-12-10)
The importance of many-body dispersion effects in layered materials subjected to high external loads is evaluated. State-of-the-art many-body dispersion density functional theory calculations performed for graphite, hexagonal boron nitride, and their heterostructures were used to fit the parameters of a
P M Vallone et al.
Nucleic acids research, 27(17), 3589-3596 (1999-08-14)
Effects of the universal base 5-nitroindole on the thermodynamic stability of DNA hairpins having a 6 bp stem and four base loops were investigated by optical absorbance and differential scanning calorimetry techniques. Melting studies were conducted in buffer containing 115
H Challa et al.
Organic letters, 1(10), 1639-1641 (2000-06-03)
[formula: see text] The syntheses of PNA oligomers containing potential ambiguous nucleobase analogues, namely 3-nitropyrrole and 5-nitroindole, have been accomplished. Hybridization properties of these PNAs with complementary oligodeoxynucleotides were evaluated by thermal denaturation experiments. Both novel residues exhibited little variation
José Gallego et al.
Nucleic acids research, 35(9), 2904-2912 (2007-04-18)
Universal bases hybridize with all other natural DNA or RNA bases, and have applications in PCR and sequencing. We have analysed by nuclear magnetic resonance spectroscopy the structure and dynamics of three DNA oligonucleotides containing the universal base analogues 5-nitroindole
C L Smith et al.
Nucleosides & nucleotides, 17(1-3), 555-564 (1998-08-26)
The 5'-triphosphate of 5-nitroindole-2'-deoxyriboside has been shown to be a good substrate for terminal deoxynucleotidyl transferase (TdT). An antibody has been prepared for the detection of 5-nitroindole and has been used for the detection of 5-nitroindole tailed DNA both in

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