AZD 1080
- Product Name
- AZD 1080
- CAS No.
- 612487-72-6
- Chemical Name
- AZD 1080
- Synonyms
- CS-809;AZD1080;AZD-1080;AZD 1080;AZD1080 ，S7145;AZD 1080;AZD-1080;AZD 1080 USP/EP/BP;AZD1080, 10 mM in DMSO;AZD1080 AZD-1080 GSK-3 Inhibitor;2-Hydroxy-3-(5-(morpholinomethyl)pyridin-2-yl)-1H-indole-5-carbonitrile
- CBNumber
- CB72666593
- Molecular Formula
- C19H18N4O2
- Formula Weight
- 334.37
- MOL File
- 612487-72-6.mol
AZD 1080 Property
- Boiling point:
- 594.0±50.0 °C(Predicted)
- Density
- 1.40±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- insoluble in H2O; insoluble in EtOH; ≥16.7 mg/mL in DMSO
- form
- solid
- pka
- 8.32±0.50(Predicted)
- color
- Light yellow to orange
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML3776
- Product name
- AZD1080
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $194.75
- Updated
- 2025/07/31
- Product number
- SML3776
- Product name
- AZD1080
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $824
- Updated
- 2025/07/31
- Product number
- 16676
- Product name
- AZD 1080
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $29
- Updated
- 2024/03/01
- Product number
- 16676
- Product name
- AZD 1080
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $102
- Updated
- 2024/03/01
- Product number
- 16676
- Product name
- AZD 1080
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $145
- Updated
- 2024/03/01
AZD 1080 Chemical Properties,Usage,Production
Description
The two isoforms of glycogen synthase kinase 3, GSK3α and GSK3β, constitutively phosphorylate and inactivate glycogen synthase, preventing glycogen synthesis. They also phosphorylate proteins that are relevant to Alzheimer’s disease and osteogenesis. AZD 1080 is a potent, brain permeable inhibitor of GSK3α and GSK3β (Kis = 6.9 and 31 nM, respectively). It shows >14-
Uses
AZD1080 is a selective, orally active, brain permeable glycogen synthase kinase-3 (GSK3) inhibitor (1,2). AZD1080 has shown to rescue synaptic plasticity deficits in rodent brain and exhibit peripheral target engagement in humans.
Definition
ChEBI: AZD1080 is a member of the class of hydroxyindoles that is 1H-indole substituted by hydroxy, 5-(morpholin-4-ylmethyl)pyridin-2-yl, and cyano groups at positions 2, 3 and 5, respectively. It is a potent, brain permeable inhibitor of human GSK3alpha and GSK3beta with Ki of 6.9 nM and 31 nM, respectively. The drug was being developed by AstraZeneca for the treatment of Alzheimer's disease (clinical trial now discontinued). It has a role as an EC 2.7.11.26 (tau-protein kinase) inhibitor, a tau aggregation inhibitor, an antineoplastic agent and an apoptosis inducer. It is a member of morpholines, a member of pyridines, a member of hydroxyindoles, a nitrile and a tertiary amino compound.
Synthesis
612488-09-2
557-21-1
612487-72-6
The reaction was carried out in a 10 mL Schlenk tube with 5-bromo-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indol-2-ol (1.00 g, 2.57 mmol), zinc powder (25.5 mg, 0.386 mmol), and bis(dibenzylideneacetone)palladium(0) (37 mg, 0.064 mmol). First, the reaction was added to the Schlenk tube along with a magnetic stirring bar, followed by sealing with a rubber septum, evacuating and displacing twice with nitrogen. Next, degassed dimethylformamide (7 mL) was added via syringe, followed by tri-tert-butylphosphine (65 μL, 20% w/v toluene solution, 0.064 mmol). The reaction mixture was heated to 50 °C with stirring and held for 4 min before zinc cyanide (169 mg, 1.42 mmol) was added under nitrogen protection. The reaction was continued with stirring at 50 °C for 3 h. HPLC analysis showed complete conversion of the reaction. After completion of the reaction, the mixture was cooled to room temperature and filtered through a sintered glass filter. To the filtrate, 3-mercaptopropyl functionalized silica (0.3 g) was added and the mixture was stirred at 40 °C overnight and filtered again. The filtrate was heated to 60 °C and tetrasodium acetate-sodium ethylenediaminetetraacetic acid (25 mL, 0.30 M aqueous solution) was added over 5 min to produce a bright yellow precipitate. The mixture was cooled to room temperature and filtered, the precipitate was washed with water (10 mL) and dried under vacuum at 40 °C to afford the target product 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indole-5-carbonitrile (0.63 g, 73% yield). The product characterization data was consistent with Example 5.
in vivo
The pharmacokinetic analysis in blood after oral administration revealed that AZD1080 has a good oral bioavailability in rats (15-24%) with a half-life of 7.1 h, making AZD1080 attractive for further in vivo testing. The subchronic (3 days) oral treatment with AZD1080 at 4 or 15 μmol/kg significantly blocked the MK-801-induced memory deficit (AZD1080 vs. MK-801, p<0.05 at 4 μmol/kg and p<0.01 at 15 μmol/kg) in mice, raising the hypothesis that longer treatment may be required to prime the synapses to function effectively[1].
target
GSK-3α
IC 50
GSK-3α: 8.2 (pKi); GSK-3β: 7.5 (pKi); cdk5: 6.4 (pKi); cdk2: 5.9 (pKi); cdk1: 5.7 (pKi)
References
[1] georgievska b1, sandin j, doherty j, mörtberg a, neelissen j, andersson a, gruber s, nilsson y, schött p, arvidsson pi, hellberg s, osswald g, berg s, fälting j, bhat rv. azd1080, a novel gsk3 inhibitor, rescues synaptic plasticity deficits in rodent brain and exhibits peripheral target engagement in humans. j neurochem. 2013 may;125(3):446-56.
AZD 1080 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from AZD 1080 manufacturers
- Product
- AZD 1080 612487-72-6
- Price
- US $2.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2018-12-24