691534
4-Nitroindole-3-carboxaldehyde
97%
Synonym(s):
3-Formyl-4-nitroindole
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About This Item
Empirical Formula (Hill Notation):
C9H6N2O3
CAS Number:
Molecular Weight:
190.16
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
Form:
solid
InChI
1S/C9H6N2O3/c12-5-6-4-10-7-2-1-3-8(9(6)7)11(13)14/h1-5,10H
SMILES string
[O-][N+](=O)c1cccc2[nH]cc(C=O)c12
InChI key
CGXVTWQTGQAMMX-UHFFFAOYSA-N
assay
97%
form
solid
mp
189-193 °C
functional group
aldehyde, nitro
Application
- reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators
- reactant in synthesis of structural analogs of thaxtomin
- reactant in preparation of chromophores related to gold fluorescent protein
- reactant in preparation of brassinin and gramine derivatives
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Yamada, F.; et al.
Heterocycles, 36, 2783-2783 (1993)
Molesworth, P., P.; et al.
Australian Journal of Chemistry, 63, 813-813 (2010)
Tetrahedron, 46, 6085-6085 (1990)
Prueger, Birgit; Bach, Thorsten.
Synthesis, 7, 1103-1103 (2007)
Eduard Dolusić et al.
Journal of medicinal chemistry, 54(15), 5320-5334 (2011-07-06)
Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active area of research in drug development. Recently, our group has shown that tryptophan 2,3-dioxygenase
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