1-AZAKENPAULLONE

ChemicalBook > CAS DataBase List > 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;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-
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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1-AZAKENPAULLONE Suppliers

Canada 1 China 62 India 1 Italy 1 Russia 1 Switzerland 1 United Kingdom 1 United States 17 Global 85

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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

9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one

676596-65-9

C15H10BrN3O

All Inhibitors

Inhibitors

Protein Kinase Inhibitors and Activators