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222410

Sigma-Aldrich

5-Methylindole

99%

Synonym(s):

NSC 522562

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About This Item

Empirical Formula (Hill Notation):
C9H9N
CAS Number:
Molecular Weight:
131.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

solid

mp

60-62 °C (lit.)

SMILES string

Cc1ccc2[nH]ccc2c1

InChI

1S/C9H9N/c1-7-2-3-9-8(6-7)4-5-10-9/h2-6,10H,1H3

InChI key

YPKBCLZFIYBSHK-UHFFFAOYSA-N

General description

The binding of 5-methylindole (inducer) to the Escherichia coli trp repressor has been studied. The mass analyzed threshold ionization spectra of jetcooled 5-methylindole (5MI) has also been studied.

Application

Reactant for preparation of:
  • Pharmaceutically active 2-oxo-1-pyrrolidine analogues
  • Potential anticancer immunomodulators
  • Preparation of antifungal agents
  • Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes
  • IL2-inducible T-cell kinase (ITK) inhibitors
  • Checkpoint 1 kinase inhibitors
  • CRTh2 antagonists
  • Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment
  • Agonists of the histamine H4 receptor
  • Monoamine reuptake inhibitors

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Jung Lee Lin et al.
The Journal of chemical physics, 120(11), 5057-5063 (2004-07-23)
The vibrationally resolved mass analyzed threshold ionization spectra of jetcooled 5-methylindole (5MI) and 3-methylindole (3MI) have been recorded by ionizing via various vibronic levels of each species. The adiabatic ionization energies (IEs) of 5MI and 3MI are determined to be
Changjiang Dong et al.
Science (New York, N.Y.), 309(5744), 2216-2219 (2005-10-01)
Chlorinated natural products include vancomycin and cryptophycin A. Their biosynthesis involves regioselective chlorination by flavin-dependent halogenases. We report the structural characterization of tryptophan 7-halogenase (PrnA), which regioselectively chlorinates tryptophan. Tryptophan and flavin adenine dinucleotide (FAD) are separated by a 10
P Babitzke et al.
The Journal of biological chemistry, 270(21), 12452-12456 (1995-05-26)
A filter binding assay was used to determine the structural features of L-tryptophan required for activation of TRAP, the trp RNA-binding attenuation protein of Bacillus subtilis. We examined the ability of L-tryptophan and 26 of its analogs to activate TRAP.
K L Westmacott et al.
Biosensors & bioelectronics, 150, 111837-111837 (2019-11-19)
This is the first report on the fabrication, characterisation and application of an electrochemical (bio)sensor system for the simultaneous measurement of skatole and androstenone. A biosensor for androstenone was fabricated using a Meldola's Blue modified SPCE (MB-SPCE) by depositing NADH
F Peter Guengerich et al.
Journal of medicinal chemistry, 47(12), 3236-3241 (2004-05-28)
Indigoids, a class of bis-indoles, represent a promising protein kinase inhibitor scaffold. Oxidation of indole by cytochrome P450 (P450) has been shown to generate species (indoxyl, isatin) that couple to yield indigo and indirubin. Escherichia coli-expressed human P450 2A6 mutants

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