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Key Documents

222410

Sigma-Aldrich

5-Methylindole

99%

Synonyme(s) :

NSC 522562

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About This Item

Formule empirique (notation de Hill):
C9H9N
Numéro CAS:
Poids moléculaire :
131.17
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Pureté

99%

Forme

solid

Pf

60-62 °C (lit.)

Chaîne SMILES 

Cc1ccc2[nH]ccc2c1

InChI

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

Clé InChI

YPKBCLZFIYBSHK-UHFFFAOYSA-N

Description générale

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

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

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
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
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.
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
Dorleta Gonzalez et al.
Bioorganic & medicinal chemistry, 26(9), 2551-2560 (2018-04-17)
Following the premises of the multitarget-directed ligands approach for the drug R&D against neurodegenerative diseases, where Alzheimer's disease (AD) outstands, we have synthesized and evaluated analogues of the gramine derivative ITH12657 (1-benzyl-5-methyl-3-(piperidin-1-ylmethyl-1H-indole, 2), which had shown important neuroprotective properties, such

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