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A93607

Sigma-Aldrich

4-Azabenzimidazole

99%

Synonym(s):

1H-Imidazo[4,5-b]pyridine

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About This Item

Empirical Formula (Hill Notation):
C6H5N3
CAS Number:
273-21-2
Molecular Weight:
119.12
EC Number:
205-987-3
MDL number:
MFCD00005579
UNSPSC Code:
12352100
eCl@ss:
32151902
PubChem Substance ID:
24891438
NACRES:
NA.22

Assay

99%

form

powder

mp

148-151 °C (lit.)

SMILES string

c1cnc2nc[nH]c2c1

InChI

1S/C6H5N3/c1-2-5-6(7-3-1)9-4-8-5/h1-4H,(H,7,8,9)

InChI key

GAMYYCRTACQSBR-UHFFFAOYSA-N

Related Categories

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Vassilios Bavetsias et al.
Bioorganic & medicinal chemistry letters, 17(23), 6567-6571 (2007-10-16)
A hit generation and exploration approach led to the discovery of 31 (2-(4-(6-chloro-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide), a potent, novel inhibitor of Aurora-A, Aurora-B and Aurora-C kinases with IC(50) values of 0.042, 0.198 and 0.227microM, respectively. Compound 31 inhibits cell proliferation and has good
Dorte Renneberg et al.
Journal of the American Chemical Society, 125(19), 5707-5716 (2003-05-08)
The DNA binding properties of fused heterocycles imidazo[4,5-b]pyridine (Ip) and hydroxybenzimidazole (Hz) paired with pyrrole (Py) in eight-ring hairpin polyamides are reported. The recognition profile of Ip/Py and Hz/Py pairs were compared to the five-membered ring pairs Im/Py and Hp/Py
Ping Lan et al.
European journal of medicinal chemistry, 46(1), 77-94 (2010-11-26)
3D-QSAR and docking studies were performed on sixty imidazo[4,5-b]pyridine derivatives as Aurora A kinase inhibitors. The CoMFA and CoMSIA models using forthy-eight molecules in the training set, gave r(cv)(2) values of 0.774 and 0.800, r(2) values of 0.975 and 0.977
Andrea Cappelli et al.
Journal of medicinal chemistry, 49(22), 6451-6464 (2006-10-27)
The 4-phenylquinoline fragment of novel AT(1) receptor antagonists 4 based on imidazo[4,5-b]pyridine moiety was replaced by 4-phenylisoquinolinone (compounds 5) or 1-phenylindene (compounds 6) scaffolds to investigate the structure-activity relationships. Binding studies showed that most of the synthesized compounds display high
M J Wanner et al.
Nucleosides, nucleotides & nucleic acids, 23(8-9), 1313-1320 (2004-12-02)
Nitration of substituted (1-deaza)purines using a mixture of tetrabutylammonium nitrate (TBAN) and trifluoracetic acid anhydride (TFAA) was applied to prepare nitrosubstituted (1-deaza)purines at low temperature. The nitro group influences the system twofold: 1) it activates other substituents towards nucleophilic aromatic
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