1,9-Pyrazoloanthrone is a chemical compound that is a derivative of anthrone

Anthrone

Anthrone is a tricyclic aromatic ketone. It is used for a popular cellulose assay and in the colorometric determination of carbohydrates....

. It is used in biochemical studies as an inhbitor

Enzyme inhibitor

An enzyme inhibitor is a molecule that binds to enzymes and decreases their activity. Since blocking an enzyme's activity can kill a pathogen or correct a metabolic imbalance, many drugs are enzyme inhibitors. They are also used as herbicides and pesticides...

 of c-Jun N-terminal kinases

C-Jun N-terminal kinases

c-Jun N-terminal kinases , were originally identified as kinases that bind and phosphorylate c-Jun on Ser-63 and Ser-73 within its transcriptional activation domain. They belong to the mitogen-activated protein kinase family, and are responsive to stress stimuli, such as cytokines, ultraviolet...

 (JNKs).

Derivatives of 1,9-pyrazoloanthrone have a variety of biological activities. For example, 5-(aminoalkyl)amino derivatives have been investigated as anticancer agents.

Synthesis

1,9-Pyrazoloanthrone can be synthesized by the condensation

Condensation reaction

A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride,...

 of 2-chloroanthraquinone with anhydrous

Anhydrous

As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another...

 hydrazine

Hydrazine

Hydrazine is an inorganic compound with the formula N2H4. It is a colourless flammable liquid with an ammonia-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually...

 in pyridine

Pyridine

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...

 at 100 °C. Purification is achieved via conversion to the N-acetyl derivative which is crystallized from acetic acid

Acetic acid

Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

, followed by hydrolysis of the acetyl group with ammonium hydroxide

Ammonium hydroxide

Ammonia solution, also known as ammonium hydroxide, ammonia water, ammonical liquor, ammonia liquor, aqua ammonia, aqueous ammonia, or simply ammonia, is a solution of ammonia in water. It can be denoted by the symbols NH3...

 in methanol

Methanol

Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

.