1,9-Pyrazoloanthrone

1,9-Pyrazoloanthrone
Names
	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
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
EC Number	204-955-6;
IUPHAR/BPS	5273;
PubChem CID	8515;
UNII	1TW30Y2766 ;
CompTox Dashboard (EPA)	DTXSID2040525 ;
	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	220.231 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)
Solubility in water	insoluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. PMC 6729938. 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): 13681–13686. Bibcode:2001PNAS...9813681B. doi:10.1073/pnas.251194298. PMC 61101. PMID 11717429.
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. PMC 6729938. 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): 13681–13686. Bibcode:2001PNAS...9813681B. doi:10.1073/pnas.251194298. PMC 61101. PMID 11717429.

[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.