1,9-Pyrazoloanthrone
| 1,9-Pyrazoloanthrone | |
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2H-Dibenzo[cd,g]indazol-6-one |
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Other names
Anthra[1,9-cd]pyrazol-6(2H)-one; Pyrazolanthrone; Pyrazoleanthrone; SP 600125; C.I. 70300; NSC 75890 |
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| Identifiers | |
| CAS number | 129-56-6 |
| PubChem | 8515 |
| ChemSpider | 8201  |
| DrugBank | DB01782 |
| ChEMBL | CHEMBL7064 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C14H8N2O |
| Molar mass | 220.23 g mol−1 |
| Appearance | yellow |
| Density | 1.463cm3 |
| Melting point |
281-282°C |
| Boiling point |
489.3°C @760mmHg |
| Solubility in water | insoluble |
| Hazards | |
| Flash point | 246.8°C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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]
[edit] 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.
[edit] References
- ^ Okuno S, Saito A, Hayashi T, Chan PH (2004). "The c-Jun N-terminal protein kinase signaling pathway mediates Bax activation and subsequent neuronal apoptosis through interaction with Bim after transient focal cerebral ischemia". J. Neurosci. 24 (36): 7879–87. doi:10.1523/JNEUROSCI.1745-04.2004. PMID 15356200. http://www.jneurosci.org/cgi/content/abstract/24/36/7879.
- ^ Showalter HD, Johnson JL, Werbel LM, Leopold WR, Jackson RC, Elslager EF (1984). "5-[(Aminoalkyl)amino]-substituted anthra[1,9-cd]pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation". J. Med. Chem. 27 (3): 253–5. doi:10.1021/jm00369a002. PMID 6699870.
