1,9-Pyrazoloanthrone

1,9-Pyrazoloanthrone

Names
IUPAC name 2H-Dibenzo[cd,g]indazol-6-one
Other names Anthra[1,9-cd]pyrazol-6(2H)-one; Pyrazolanthrone; Pyrazoleanthrone; SP 600125; C.I. 70300; NSC 75890
Identifiers
CAS Number	129-56-6
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:90695
ChEMBL	ChEMBL7064
ChemSpider	8201
DrugBank	DB01782
ECHA InfoCard	100.004.506
IUPHAR/BPS	5273
PubChem	8515
InChI InChI=1S/C14H8N2O/c17-14-9-5-2-1-4-8(9)13-12-10(14)6-3-7-11(12)15-16-13/h1-7H,(H,15,16) Key: ACPOUJIDANTYHO-UHFFFAOYSA-N InChI=1/C14H8N2O/c17-14-9-5-2-1-4-8(9)13-12-10(14)6-3-7-11(12)15-16-13/h1-7H,(H,15,16) Key: ACPOUJIDANTYHO-UHFFFAOYAB
SMILES C1=CC=C2C(=C1)C3=NNC4=CC=CC(=C43)C2=O O=C4c1cccc2c1c(nn2)c3ccccc34
Properties
Chemical formula	C14H8N2O
Molar mass	220.23 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)
Solubility in water	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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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][2]

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.

References

1. 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.
2. Bennett, B. L.; Sasaki, D. T.; Murray, B. W.; O'Leary, E. C.; Sakata, S. T.; Xu, W.; Leisten, J. C.; Motiwala, A.; Pierce, S.; Satoh, Y.; Bhagwat, S. S.; Manning, A. M.; Anderson, D. W. (2001). "SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase". Proceedings of the National Academy of Sciences. 98 (24): 13681. Bibcode:2001PNAS...9813681B. doi:10.1073/pnas.251194298.
3. 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.