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525022

Sigma-Aldrich

4-Aminoindole

97%

Synonym(s):

(Indol-4-yl)amine, 4-Indolamine

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About This Item

Empirical Formula (Hill Notation):
C8H8N2
CAS Number:
5192-23-4
Molecular Weight:
132.16
Beilstein/REAXYS Number:
114919
MDL number:
MFCD01076559
UNSPSC Code:
12352100
PubChem Substance ID:
24874461
NACRES:
NA.22

assay

97%

mp

106-109 °C (lit.)

SMILES string

Nc1cccc2[nH]ccc12

InChI

1S/C8H8N2/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,9H2

InChI key

LUNUNJFSHKSXGQ-UHFFFAOYSA-N

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General description

4-Aminoindole is an indole derivative. Its cytokinin activity has been assessed by tobacco pith callus bioassay. 4-Aminoindole can be prepared by reacting 2,6-dinitrotoluene and N,N-dimethylformamide dimethylacetal in anhydrous DMF.

Application

4-Aminoindole may be used to synthesize:
  • macrolactam tumour promoter indolactam V
  • tricyclic structure of 2-substituted-pyrrolo[2,3-h]quinolin-4-one
  • 4-azidoindole
Reactant for preparation of:
  • Inhibitors of bacterial thymidylate synthase
  • Mimetics of non-alkaloid toxin lignan anticancer and antiviral agent Podophyllotoxin (PPT)
  • Inhibitors of Gli1-mediated transcription in the Hedgehog pathway
  • Protein kinase C θ (PKCθ) inhibitors
  • Indolic non-peptidic HIV protease inhibitors
  • Transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonists
  • Cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors
  • 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1) inhibitors
  • Short chain 4-substituted indoles as potent αvβ3 antagonist
  • Ligands of serotonin transporter and 5-HT1A receptors

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Cytokinin activity of azaindene, azanaphthalene, naphthalene, and indole derivatives.
Torigoe Y, et al.
Phytochemistry, 11(5), 1623-1630 (1972)
Synthestic approaches to the teleocidin-related tumour promoters: a total synthesis of (?)-indolactam V.
de Laszlo SE, et al.
Journal of the Chemical Society. Chemical Communications, 4, 344-346 (1986)
An efficient synthesis of azidoindoles and azidotryptophans.
Melhado LL and Leonard NJ.
The Journal of Organic Chemistry, 48(25), 5130-5133 (1983)
Maria Grazia Ferlin et al.
Journal of medicinal chemistry, 48(9), 3417-3427 (2005-04-29)
In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26

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