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About This Item
Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
Molecular Weight:
147.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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[1].
- Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators[2]
- Reactant for preparation of indolylindazoles and indolylpyrazolopyridines as interleukin-2 inducible T cell kinase inhibitors[3]
- Reactant for preparation of benzoylpiperazinyl-indolyl ethane dione derivatives as HIV-1 inhibitors[4]
- Reactant for preparation of bis(indolyl)alkanehydroxamic acids as histone deacetylase inhibitors[5]
- Reactant for preparation of β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2[6]
Biochem/physiol Actions
7-Methoxyindole inhibits tobacco cell growth that can be partially reversed by indole and tryptophan[7].
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
>235.4 °F - closed cup
Flash Point(C)
> 113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Trujillo, J., I.; et al.
Bioorganic & Medicinal Chemistry Letters, 19, 2365-2365 (2009)
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
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
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
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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