1,9-Pyrazoloanthrone
Chemical compound
From Wikipedia, the free encyclopedia
1,9-Pyrazoloanthrone is a chemical compound that is a derivative of anthrone. It is used in biochemical studies as an inhibitor of c-Jun N-terminal kinases (JNKs).[1][2]
| Names | |
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| Preferred IUPAC name
Dibenzo[cd,g]indazol-6(2H)-one | |
| Other names
Anthra[1,9-cd]pyrazol-6(2H)-one; Pyrazolanthrone; Pyrazoleanthrone; SP 600125; C.I. 70300; NSC 75890 | |
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| DrugBank | |
| ECHA InfoCard | 100.004.506 |
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| Properties | |
| C14H8N2O | |
| Molar mass | 220.231 g·mol−1 |
| Appearance | yellow |
| Density | 1.463 g cm−3 |
| Melting point | 281 to 282 °C (538 to 540 °F; 554 to 555 K) |
| insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Derivatives of 1,9-pyrazoloanthrone have a variety of biological activities. For example, 5-(aminoalkyl)amino derivatives have been investigated as anticancer agents.[3]
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.
