ChemicalBook > CAS DataBase List > 1-AZAKENPAULLONE

1-AZAKENPAULLONE

Product Name
1-AZAKENPAULLONE
CAS No.
676596-65-9
Chemical Name
1-AZAKENPAULLONE
Synonyms
azakenpaullone;1-AZAKENPAULLONE;1-Azakenpaullone (1-Akp);1-AZAKENPAULLONE USP/EP/BP;InSolution? 1-Azakenpaullone;1-Azakenpaullone - CAS 676596-65-9 - Calbiochem;InSolution 1-Azakenpaullone - CAS 676596-65-9 - Calbiochem;9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one;Pyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one, 9-broMo-7,12-dihydro-;1-Azakenpaullone 9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one
CBNumber
CB6803762
Molecular Formula
C15H10BrN3O
Formula Weight
328.16
MOL File
676596-65-9.mol
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1-AZAKENPAULLONE Property

Melting point:
>290°C (dec.)
Boiling point:
648.8±50.0 °C(Predicted)
Density 
1.655±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: >10mg/mL
pka
13.36±0.20(Predicted)
form 
Tan solid
color 
gray-brown
InChI
InChI=1S/C15H10BrN3O/c16-8-3-4-11-9(6-8)10-7-13(20)18-12-2-1-5-17-15(12)14(10)19-11/h1-6,19H,7H2,(H,18,20)
InChIKey
NTSBZVCEIVPKBJ-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(Br)C=C2)C2CC(=O)NC3=CC=CN=C3C1=2
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Safety

WGK Germany 
2
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
191501
Product name
InSolution 1-Azakenpaullone - CAS 676596-65-9 - Calbiochem
Purity
A Kenpaullone analog that acts as a potent and ATP-competitive inhibitor of GSK-3&beta.
Packaging
500μg
Price
$96.4
Updated
2023/01/07
Sigma-Aldrich
Product number
191500
Product name
1-Azakenpaullone
Packaging
1mg
Price
$155
Updated
2022/05/15
Cayman Chemical
Product number
16733
Product name
1-Azakenpaullone
Purity
≥98%
Packaging
1mg
Price
$92
Updated
2024/03/01
Cayman Chemical
Product number
16733
Product name
1-Azakenpaullone
Purity
≥98%
Packaging
5mg
Price
$295
Updated
2024/03/01
Sigma-Aldrich
Product number
A3734
Product name
1-Azakenpaullone
Purity
≥97% (HPLC)
Packaging
1mg
Price
$142
Updated
2024/03/01
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1-AZAKENPAULLONE Chemical Properties,Usage,Production

Chemical Properties

Tan Solid

Uses

A selective inhibitor of glycogen synthase kinase-3β.

Definition

ChEBI: 1-azakenpaullone is an organic heterotetracyclic compound that is 7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indole substituted at positions 6 and 9 by oxo and bromo groups respectively. It has a role as an EC 2.7.11.26 (tau-protein kinase) inhibitor and a Wnt signalling activator. It is an organic heterotetracyclic compound, an organonitrogen heterocyclic compound, a lactam and an organobromine compound.

General Description

A Kenpaullone (>Cat. No. 422000) analog that acts as a potent and ATP-competitive inhibitor of GSK-3β (IC50 = 18 nM). Displays over 100-fold greater selectivity over Cdk1/cyclin B and Cdk5/p25 (IC50 = 2.0 μM and 4.2 μM, respectively). The solid form of this compound (Cat. No. 191500) is also available.

Biological Activity

1-azakenpaullone is a selective and cell-permeable inhibitor of glycogen synthase kinase-3β (gsk-3β) with ic50 value of 18nm [1, 2].1-azakenpaullone is a kenpaullone derivative with a modified heterocyclic basic structure. it shows potent inhibitory activity against gsk-3β over cdk1/cyclin b and cdk5/p25. the ic50 values for cdk1/cyclin b, cdk5/p25 and gsk-3β are 2μm, 4.2μm and 18nm, respectively. as an inhibitor of gsk-3β, 1-azakenpaullone is developed as potential antidiabetic drug. 1-azakenpaullone is found to protect rat insulinoma cell line ins-1e cells from glucolipotoxicity and stimulate cell proliferation. besides that, 1-azakenpaullone promotes the replication of beta cells in isolated rat islets at concentration of 1μm. in addition, 1-azakenpaullone is reported to have effect in changing cardiac myocyte morphology. it increases cell area primarily through the elongation of the cells [1, 2 and 3].

Biochem/physiol Actions

Cell permeable: yes

Enzyme inhibitor

This cell-permeable protein kinase inhibitor (FW = 328.17 g/mol; CAS 676596-65-9: Solubility: 66 mg/mL DMSO; <1 mg/mL H2O), also named 9-bromo-7,12-dihydro-pyrido[3,2’:2,3]azepino[4,5-b]indol-6(5H)-one, selectively and potently targets glycogen synthase kinase 3β, or GSK3β (IC50 = 18 nM) with 100x less inhibitory action against cyclin-dependent kinases (CDKs). 1-Azakenpaullone has become a gold standard for GSK3 inhibition.

target

GSK-3β

storage

+4°C

References

[1] kunick c, lauenroth k, leost m, et al. 1-azakenpaullone is a selective inhibitor of glycogen synthase kinase-3β. bioorganic & medicinal chemistry letters, 2004, 14(2): 413-416.
[2] mussmann r, geese m, harder f, et al. inhibition of gsk3 promotes replication and survival of pancreatic beta cells. journal of biological chemistry, 2007, 282(16): 12030-12037.
[3] markou t, cullingford t e, giraldo a, et al. glycogen synthase kinases 3α and 3β in cardiac myocytes: regulation and consequences of their inhibition. cellular signalling, 2008, 20(1): 206-218.

1-AZAKENPAULLONE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 1-AZAKENPAULLONE manufacturers

Career Henan Chemical Co
Product
1-AZAKENPAULLONE 676596-65-9
Price
US $1.00/KG
Min. Order
1KG
Purity
95--99%
Supply Ability
1ton
Release date
2020-01-03

676596-65-9, 1-AZAKENPAULLONERelated Search:

MANZAMINE A AR-A014418 SB216763 Ethacrynic acid 4-BENZYL-2-METHYL-1,2,4-THIADIAZOLIDINE-3,5-DIONE SB 415286 KAHWEOL SEDANOLIDE S-[N-(3-PHENYLPROPYL)(THIOCARBAMOYL)]-L-CYSTEINE CAFESTOL 2-THIO(3-IODOBENZYL)-5-(1-PYRIDYL)-[1,3,4]-OXADIAZOLE Laurocapram 1-AZAKENPAULLONE, >95%

  • 1-AZAKENPAULLONE
  • 9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one
  • Pyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one, 9-broMo-7,12-dihydro-
  • InSolution? 1-Azakenpaullone
  • 1-Azakenpaullone 9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one
  • InSolution 1-Azakenpaullone - CAS 676596-65-9 - Calbiochem
  • 1-Azakenpaullone - CAS 676596-65-9 - Calbiochem
  • azakenpaullone
  • 1-AZAKENPAULLONE USP/EP/BP
  • 1-Azakenpaullone (1-Akp)
  • Glycogen synthase kinase-3,1 Azakenpaullone,GSK-3,1-Azakenpaullone,1Azakenpaullone,Glycogen synthase kinase 3,Inhibitor,inhibit,1-Akp
  • 676596-65-9
  • C15H10BrN3O
  • All Inhibitors
  • Inhibitors
  • Protein Kinase Inhibitors and Activators