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Anthra(1,9-cd)pyrazol-6(2H)-one

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Anthra(1,9-cd)pyrazol-6(2H)-one

1,9-Pyrazoloanthrone
Identifiers
CAS number 129-56-6 N
PubChem 8515
ChemSpider 8201 YesY
DrugBank DB01782
Jmol-3D images Image 2
Properties
Molecular formula C14H8N2O
Molar mass 220.23 g mol−1
Appearance yellow
Density 1.463 g cm−3
Melting point

281-282 °C, 554-555 K, 538-540 °F

Boiling point

489 °C, 762 K, 912 °F

Solubility in water insoluble
Hazards
Flash point 246.8 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,9-Pyrazoloanthrone is a chemical compound that is a derivative of anthrone. It is used in biochemical studies as an inhbitor of c-Jun N-terminal kinases (JNKs).[1]

Derivatives of 1,9-pyrazoloanthrone have a variety of biological activities. For example, 5-(aminoalkyl)amino derivatives have been investigated as anticancer agents.[2]

Synthesis

1,9-Pyrazoloanthrone can be synthesized by the condensation of 2-chloroanthraquinone with anhydrous hydrazine in pyridine at 100 °C. Purification is achieved via conversion to the N-acetyl derivative which is crystallized from acetic acid, followed by hydrolysis of the acetyl group with ammonium hydroxide in methanol.

References

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