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A95502

Sigma-Aldrich

7-Azaindole

98%

Synonym(s):

1H-Pyrrolo(2,3-b)pyridine

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About This Item

Empirical Formula (Hill Notation):
C7H6N2
CAS Number:
271-63-6
Molecular Weight:
118.14
EC Number:
205-981-0
MDL number:
MFCD00005606
UNSPSC Code:
12352100
PubChem Substance ID:
24891472
NACRES:
NA.22

Assay

98%

form

solid

mp

105-107 °C (lit.)

SMILES string

c1cnc2[nH]ccc2c1

InChI

1S/C7H6N2/c1-2-6-3-5-9-7(6)8-4-1/h1-5H,(H,8,9)

InChI key

MVXVYAKCVDQRLW-UHFFFAOYSA-N

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Related Categories

Application

A heterocyclic molecule that can be utilized as a pharmaceutical building block
Starting material in a recent synthesis of azaserotonin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Pei-Wen Wu et al.
Journal of the American Chemical Society, 128(45), 14426-14427 (2006-11-09)
We report the synthesis of 3-(2-aminoethyl)-5-ol-1H-pyrrolo[2,3-b]pyridine (7-azaserotonin), which may potentially serve as an agonist or antagonist of serotonin receptors. In alcohols, the solvent (e.g., ethanol) catalyzed proton-transfer reaction takes place for 7-azaserotonin in the excited state, resulting in dual emission.
John J Caldwell et al.
Journal of medicinal chemistry, 51(7), 2147-2157 (2008-03-19)
Fragment-based screening identified 7-azaindole as a protein kinase B inhibitor scaffold. Fragment elaboration using iterative crystallography of inhibitor-PKA-PKB chimera complexes efficiently guided improvements in the potency and selectivity of the compounds, resulting in the identification of nanomolar 6-(piperidin-1-yl)purine, 4-(piperidin-1-yl)-7-azaindole, and
Alastair Donald et al.
Journal of medicinal chemistry, 50(10), 2289-2292 (2007-04-25)
6-phenylpurines were identified as novel, ATP-competitive inhibitors of protein kinase B (PKB/Akt) from a fragment-based screen and were rapidly progressed to potent compounds using iterative protein-ligand crystallography with a PKA-PKB chimeric protein. An elaborated lead compound showed cell growth inhibition
Xin Wang et al.
The Journal of organic chemistry, 71(10), 4021-4023 (2006-05-06)
A practical synthesis of a key pharmaceutical intermediate, 2-[(1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino]-5-fluoronicotinic acid (1), is described. To introduce the aminomethyl moiety of 2 via a palladium-catalyzed cyanation/reduction sequence, a regioselective chlorination of 7-azaindole via the N-oxide was developed. A highly selective monodechlorination of
Bruno Aleksander Martek et al.
Drug testing and analysis, 11(4), 617-625 (2019-02-08)
The high frequency of the synthetic cannabinoid receptor agonists (SCRAs) emergence renders this group of new psychoactive compounds particularly demanding in terms of detection, identification, and responding. Without the available reference material, one of the specific problems is differentiation and
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