349593
6-Fluoroindole
98%
Synonym(s):
NSC 520436
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About This Item
Empirical Formula (Hill Notation):
C8H6FN
CAS Number:
Molecular Weight:
135.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
112192
Assay:
98%
InChI
1S/C8H6FN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H
SMILES string
Fc1ccc2cc[nH]c2c1
InChI key
YYFFEPUCAKVRJX-UHFFFAOYSA-N
assay
98%
Quality Level
mp
72-76 °C (lit.)
functional group
fluoro
General description
6-Fluoroindole is a halogen substituted indole. Experimental ionization potential of 6-fluoroindole has been evaluated. Preparation of 6-fluoroindole via nitration of indoline has been reported.
Application
6-Fluoroindole may be used as reactant in the preparation of:
- tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- antibacterial agents
- antifungal agents
- Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the management of hyperglycemia in diabetes
- potent selective serotonin reuptake inhibitors
- inhibitors of HIV-1 attachment
signalword
Warning
hcodes
Hazard Classifications
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, Gloves
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Chun-Hsu Yao et al.
Journal of medicinal chemistry, 54(1), 166-178 (2010-12-07)
A novel series of N-linked β-D-xylosides were synthesized and evaluated for inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) in a cell-based assay. Of these, the 4-chloro-3-(4-cyclopropylbenzyl)-1-(β-D-xylopyranosyl)-1H-indole 19m was found to be the most potent inhibitor, with an EC(50) value
Journal of Medicinal Chemistry, 36, 2242-2242 (1993)
H Dalton King et al.
Journal of medicinal chemistry, 53(21), 7564-7572 (2010-10-19)
A series of conformationally restricted homotryptamines has been synthesized and shown to be potent inhibitors of hSERT. Conformational restriction of the homotryptamine side chain was attained by the insertion of a cyclopentyl ring, with the indole ring and the terminal
J L Malleron et al.
Journal of medicinal chemistry, 36(9), 1194-1202 (1993-04-30)
A series of new indole derivatives (2-28) has been prepared in the search for novel 5-HT uptake inhibitors. These compounds were obtained by the condensation of N-(chloroalkyl) naphthalenesultam derivatives with the appropriate amine in presence of a base, at reflux
S Jimmy Budiardjo et al.
ACS synthetic biology, 5(12), 1475-1484 (2016-07-09)
Chemical biology has long sought to build protein switches for use in molecular diagnostics, imaging, and synthetic biology. The overarching challenge for any type of engineered protein switch is the ability to respond in a selective and predictable manner that
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