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694681

Sigma-Aldrich

7-Azaindole-3-carboxaldehyde

97%

Synonym(s):

1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

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About This Item

Empirical Formula (Hill Notation):
C8H6N2O
CAS Number:
4649-09-6
Molecular Weight:
146.15
MDL number:
MFCD03407363
UNSPSC Code:
12352100
PubChem Substance ID:
329761677
NACRES:
NA.22

assay

97%

form

solid

mp

216-220 °C

SMILES string

O=Cc1c[nH]c2ncccc12

InChI

1S/C8H6N2O/c11-5-6-4-10-8-7(6)2-1-3-9-8/h1-5H,(H,9,10)

InChI key

KAIWRKYDYWYFIT-UHFFFAOYSA-N

Application

Reactant for preparation of:
  • Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Inhibitors of BACE-1 activity
  • Prostate cancer invasion and migration inhibitors
  • CDK2 kinase inhibitors
  • Cell division cycle 7 kinase inhibitors
  • Inhibitor of oncogenic B-Raf kinase with potent antimelanoma activity
  • Antidiabetic agents
  • Inhibitors of brassinin glucosyltransferase
Useful starter in 7-azaindole chemistry

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Seung-Jun Oh et al.
Bioorganic & medicinal chemistry, 12(21), 5505-5513 (2004-10-07)
Seven fluorine-substituted 1H-pyrrolo[2,3-b]pyridine derivatives were synthesized based on a lead ligand, 3-[[4-(4-iodophenyl)piperazin-1-yl]-methyl]-1H-pyrrolo[2,3-b]pyridine (L-750,667) and evaluated as potential dopamine D(4) receptor imaging agents by positron emission tomography (PET). Binding affinities of these ligands for the dopamine D(2), D(3), and D(4) receptor
Synthesis of 1-p-chlorobenzyl-7-azaindole-3- -piperidylmethanol as a potential antimalarial agent.
A J Verbiscar
Journal of medicinal chemistry, 15(2), 149-152 (1972-02-01)
Journal of the American Chemical Society, 77, 457-457 (1995)
Ming-Zhi Zhang et al.
European journal of medicinal chemistry, 92, 776-783 (2015-01-31)
Streptochlorin, first isolated as a new antibiotic in 1988 from the lipophilic extracts of the mycelium of a Streptomyces sp, is an indole natural products with a variety of biological activities. Based on the methods developed for the synthesis of

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