1,9-Pyrazoloanthrone Chemical Properties

Melting point:

281~282℃

Boiling point:

361.16°C (rough estimate)

Density 

1.1702 (rough estimate)

refractive index 

1.5910 (estimate)

storage temp. 

2-8°C

solubility 

H₂O: insoluble

form 

Yellowish orange solid

pka

11.75±0.20(Predicted)

color 

yellow

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months

InChIKey

ACPOUJIDANTYHO-UHFFFAOYSA-N

CAS DataBase Reference

129-56-6(CAS DataBase Reference)

EPA Substance Registry System

Anthra[1,9-cd]pyrazol-6(2H)-one (129-56-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

CB4585000

TSCA 

Yes

HS Code 

29339900

Toxicity

LD50 ivn-mus: 178 mg/kg CSLNX* NX#00640

MSDS

• Language:English Provider:SigmaAldrich

1,9-Pyrazoloanthrone Usage And Synthesis

Description

SP-600125 (129-56-6) is a selective inhibitor of c-Jun N-terminal kinase (JNK). Reversibly inhibits JNK1,2 and 3 (IC50‘s range from 40-90 nM). >300-fold selectivity for JNK as compared to related MAP kinases. Anti-inflammatory activity. SP-600125 inhibits expression of presenilin-1 and Notch signaling in mouse brain. Cell permeable and active in vivo.

Uses

C2C12 myoblasts were treated with SP600125 to test the stimulation of myogenesis.¹¹ It was used to treat HepG2 cells to test the effects on oxysterol-induced necrosis.¹²

Uses

A broad-spectrum serine/threonine kinase inhibitor of JNK with an IC50 range from 40 to 90 nM.

Uses

SP 600125 is a Jun N-terminal kinase (JNK) inhibitor.

Definition

ChEBI: A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.

General Description

A potent, cell-permeable, selective, and reversible inhibitor of c-Jun N-terminal kinase (JNK) (IC₅₀ = 40 nM for JNK-1 and JNK-2 and 90 nM for JNK-3). The inhibition is competitive with respect to ATP. Exhibits over 300-fold greater selectivity for JNK as compared to ERK1 and p38-2 MAP kinases. Inhibits the phosphorylation of c-Jun and blocks the expression of IL-2, IFN-γ, TNF-α, and COX-2 in cells. Blocks IL-1-induced accumulation of phospho-Jun and induction of c-Jun transcription.

Biological Activity

Selective inhibitor of c-Jun N-terminal kinase (JNK). Competitively and reversibly inhibits JNK1, 2 and 3 (IC 50 = 40-90 nM) with negligible activity at ERK2, p38 β and a range of enzymes (IC 50 > 10 μ M). Active in vivo . Shown to have reduced selectivity over other protein kinases under certain conditions. Protects renal tubular epithelial cells against ischemia/reperfusion-induced apoptosis. Also available as part of the MAPK Inhibitor Tocriset™ .

Biochem/physiol Actions

SP600125 is an anthrapyrazolone inhibitor of JNK that competes with ATP to inhibit the phosphorylation of c-Jun. It prevents the activation of inflammatory genes such as COX-2, IL-2 IFN-γ and TNF-α.8,9 It prevents the activation of JNK after brain ischemia and may be effective in treatment of ischemic stroke.10

Safety Profile

Poison by intravenous route.When heated to decomposition it emits toxic fumes ofNOx.

Synthesis

1,9-Pyrazolanthrone is prepared by diazotization of 1-aminoanthraquinone, reaction of the diazonium salt with sodium hydrogen sulfite, and cyclization of the resulting hydrazinosulfonic acid .

storage

-20°C (desiccate)

References

1)Bennett et al. (2001), SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase; Proc. Natl. Acad. Sci. USA., 98 13681 2) Rahman et al. (2012), Intraperitoneal injection of JNK-specific inhibitor SP600125 inhibits the expression of presenilin-1 and Notch signaling in mouse brain without induction of apoptosis; Brain Res., 1448 117

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