1,9-Pyrazoloanthrone

changed changed 477206828 1,9-Pyrazoloanthrone.png 200px Dibenzo[cd,g]indazol-6(2H)-one Anthra[1,9-cd]pyrazol-6(2H)-one; Pyrazolanthrone; Pyrazoleanthrone; SP 600125; C.I. 70300; NSC 75890 5273 correct chemspider 8201 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) ACPOUJIDANTYHO-UHFFFAOYAB correct EBI 7064 changed EBI 90695 204-955-6 correct chemspider 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) correct chemspider ACPOUJIDANTYHO-UHFFFAOYSA-N correct CAS 129-56-6 correct FDA 1TW30Y2766 8515 correct drugbank DB01782 O=c2c1ccccc1c4n[nH]c3cccc2c34 14 8 2 1 yellow 1.463 g cm−3 281 to 282 insoluble 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).Okuno S, Saito A, Hayashi T, Chan PH 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 2004 15356200 10.1523/JNEUROSCI.1745-04.2004 6729938 free 10.1073/pnas.251194298 SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase Proceedings of the National Academy of Sciences 98 24 13681–13686 2001 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. 2001PNAS...9813681B 61101 11717429 free Derivatives of 1,9-pyrazoloanthrone have a variety of biological activities. For example, 5-(aminoalkyl)amino derivatives have been investigated as anticancer agents.Showalter HD, Johnson JL, Werbel LM, Leopold WR, Jackson RC, Elslager EF 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 1984 6699870 10.1021/jm00369a002 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 Category:Aromatic ketones Category:Nitrogen heterocycles Category:Heterocyclic compounds with 4 rings Category:Tetracyclic compounds