1,9-Pyrazoloanthrone

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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 Edit this at Wikidata
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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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

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