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113980

Sigma-Aldrich

7-Methoxyindole

97%

Synonym(s):

NSC 100739

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About This Item

Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
3189-22-8
Molecular Weight:
147.17
EC Number:
221-690-1
MDL number:
MFCD00047203
UNSPSC Code:
12352100
PubChem Substance ID:
24847155

assay

97%

refractive index

n20/D 1.612 (lit.)

bp

108-110 °C/0.3 mmHg (lit.)

density

1.126 g/mL at 25 °C (lit.)

SMILES string

COc1cccc2cc[nH]c12

InChI

1S/C9H9NO/c1-11-8-4-2-3-7-5-6-10-9(7)8/h2-6,10H,1H3

InChI key

FSOPPXYMWZOKRM-UHFFFAOYSA-N

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Application

7-Methoxyindole is used to study the effects of methoxy and amino substitution on the indole ring.
  • Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Reactant for preparation of indolylindazoles and indolylpyrazolopyridines as interleukin-2 inducible T cell kinase inhibitors
  • Reactant for preparation of benzoylpiperazinyl-indolyl ethane dione derivatives as HIV-1 inhibitors
  • Reactant for preparation of bis(indolyl)alkanehydroxamic acids as histone deacetylase inhibitors
  • Reactant for preparation of β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2

Biochem/physiol Actions

7-Methoxyindole inhibits tobacco cell growth that can be partially reversed by indole and tryptophan.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Matthias Herdemann et al.
Bioorganic & medicinal chemistry letters, 20(23), 6998-7003 (2010-10-23)
A series of novel compound libraries inhibiting interleukin-2 inducible T cell kinase (ITK) were designed, synthesized and evaluated. In the first design cycle two library scaffolds were identified showing low micromolar inhibition of ITK. Further iterative design cycles including crystal
Giuseppe Giannini et al.
Bioorganic & medicinal chemistry letters, 19(10), 2840-2843 (2009-04-11)
In order to gather further knowledge about the structural requirements on histone deacetylase inhibitors (HDACi), starting from the schematic model of the common pharmacophore that characterizes this class of molecules (surface recognition CAP group-connection unit-linker region-Zinc Binding Group), we designed
D W Miles et al.
Proceedings of the National Academy of Sciences of the United States of America, 70(12), 3754-3758 (1973-12-01)
The magnetic circular dichroism of benzene and indole derivatives was measured down to 190 nM. The following pairs of molecules have magnetic circular dichroisms of the opposite sign in the B(2u) absorption region: aniline and benzonitrile, indene and indoline, indole
Trujillo, J., I.; et al.
Bioorganic & Medicinal Chemistry Letters, 19, 2365-2365 (2009)
J M Widholm
Plant physiology, 67(6), 1101-1104 (1981-06-01)
Twenty-three indole analogs were used to inhibit the growth of carrot and tobacco suspension cultures. The addition of tryptophan or indole partially reversed the inhibition of both cell lines only for 4-fluoroindole, 5-fluoroindole, and 6-fluoroindole. Inhibition of tobacco cell growth
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