5203-80-5

Usage

Structure

Acetate ester of 1-acetyl-1H-indazol-3-ol, a derivative of the heterocyclic indazole structure

Potential function

Inhibitor of histone deacetylase

Enzyme target

Histone deacetylase, an enzyme involved in the regulation of gene expression and cell growth

Potential application

Anti-cancer properties, as histone deacetylase inhibitors have shown promise in the treatment of various cancers

Other potential applications

Pharmacological activities and potential applications in drug development and research

Upstream product

• 5203-85-0 1,2-Diacetyl-1,2-dihydro-3H-indazol-3-one 
• 108-24-7 acetic anhydride 
• 7384-18-1 1-Acetyl-1,2-dihydro-3H-indazol-3-one 
• 102787-68-8 1,2-Dihydro-1,2-dipropionyl-3H-indazol-3-one 
• 7364-25-2 3-indazolinone 
• 102787-71-3 1-Acetyl-1,2-dihydro-2-propionyl-3H-indazol-3-one 
• 7384-19-2 2-Acetyl-1,2-dihydro-3H-indazol-3-one 
• 5326-27-2 2-hydrazino-benzoic acid 
• 102787-73-5 1-Acetyl-2-butyryl-1,2-dihydro-indazol-3-one 
• 102787-54-2 o-(N-butanoylhydrazino)benzoic acid 
• 102787-53-1 o-(N-propanoylhydrazino)benzoic acid 
• 99071-82-6 1,2-Dihydro-2-propionyl-3H-indazol-3-one 
• 102787-49-5 1-(3-Hydroxy-indazol-2-yl)-ethanone 
• 26537-65-5 3-(o-Carboxyphenyl)sydnone 

Relevant academic research and scientific papers

Kinetically deduced existence of C=O·····C close contacts. Pericyclic rearrangement of 1,2-diacetyl-1,2-dihydro-3H-indazol-3-one

First-order kinetics of the title rearrangement to 3-acetoxy-1-acetylindazole (2a), complete exchange of O-acyl groups in cross-experiments, insensitivity to change in reaction medium, lack of electronic substituent effects and activation parameters are considered as evidence in favour of a pericyclic mechanism through C=O·····C close contacts.

REVERSE MUMM REARRANGEMENTS. I. THERMOLYSIS OF 3-ACETOXY-1-FORMYLINDAZOLE

2-Acetyl-3-indazolone (15), 1,2-diacetyl-3-indazolone (16) and 3-acetoxy-1-acetylindazole (3) are intermediates of the title thermolysis which leads to 1-acetyl-3-indazolone (4). The rearrangement of 16 to 3 is a reverse Mumm rearrangement which has not yet been observed. The same pattern applies to the acetylation of the 3-indazolone (2). Acylotropic equilibria have been observed between 2-acetyl-1-methyl-3-indazolone (24) and 3-acetoxy-1-methylindazole (26).

NEW CONVENIENT METHODS FOR THE SYNTHESIS OF 1,2-DIHYDRO-3H-INDAZOL-3-ONE AND ITS 1-ACYL DERIVATIVES

The acid hydrolysis of the readily obtainable 3-(o-carboxyphenyl)sydnones (6a-d) afforded 3-indazolones (3a-d) in yields over 90 percent. By transacylation between 1-acyl-3-acyloxyindazoles (11a-d) and 3-indazolones (3a, c), the corresponding 1-acyl-3-indazolones 10a-d resulted in pure state and yields also over 90 percent.

Acyl Derivatives of Indazolin-3-one

1- and 2-Ethanoyl-, propanoyl-, butanoyl- and benzoylindazolin-3-ones have been prepared and the 2-isomers have been shown to exist in two tautomeric forms.Sulphonylation and further acylation of these compounds are described and some rearrangements in the series are discussed.