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 (JSmol)	Interactive image;
ChEBI	CHEBI:90695 ;
ChEMBL	ChEMBL7064 ;
ChemSpider	8201 ;
DrugBank	DB01782 ;
ECHA InfoCard	100.004.506
IUPHAR/BPS	5273;
PubChem CID	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 O=c2c1ccccc1c4n[nH]c3cccc2c34;
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 inhibitor 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

↑ 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.
↑ 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. PMC 61101.
↑ 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.

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[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. PMC 61101.

[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.