1,9-Pyrazoloanthrone

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]

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.506
EC Number
  • 204-955-6
UNII
  • 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) checkY
    Key: ACPOUJIDANTYHO-UHFFFAOYSA-N checkY
  • 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
  • O=c2c1ccccc1c4n[nH]c3cccc2c34
Properties
C14H8N2O
Molar mass 220.231 g·mol−1
Appearance yellow
Density 1.463 g cm3
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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Infobox references

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. 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.
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