5394-42-3

Usage

Chemical structure

heterocyclic compound with a pyrazolo[3,4-d]pyrimidin-4-one core structure

Application

medicinal chemistry and drug development
Potential therapeutic activities
Specific context and application may influence properties and uses
Varied properties and uses depending on specific application

Upstream product

• 554-12-1 propanoic acid methyl ester 
• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 115-80-0 Triethyl orthopropionate 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 

Downstream Products

• 1081266-51-4 N-propyl-6-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1383659-10-6 N-isopropyl-6-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1383659-11-7 N-butyl-6-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1383659-12-8 N-furfuryl-6-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1081242-97-8 6-ethyl-4-(morpholin-4-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 1383659-13-9 6-ethyl-N,1-diphenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 205753-31-7 4-Chloro-6-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Synthesis of novel 2-alkyl-4-substituted-amino-pyrazolo[3,4-d]pyrimidines as new leads for anti-bacterial and anti-cancer activity

Treatment of 6-alkyl-1-phenyl-4-chloro-(1H)-pyrazolo[3,4-d]pyrimidines, with different amines afforded a series of compounds whose identity and purity were confirmed by spectral and analytical means. The compounds were tested for antibacterial activity against four organisms viz. Staphylococcus aureus (Gram positive), S. epidermidis (Gram positive), Bacillus subtilis (Gram positive), Escherichia coli (Gram negative) using amoxicillin as standard control. Compounds 4d, 6b, 6c have shown best antibacterial activity in the series. The antiproliferative activity was tested against human skin cancer cell line G361. The compounds 3d, 4d, 5b, 5d, 5e, 6c, 7a were found to be the best of the series and showed the activity at micromolar concentration.

Montmorillonite K10 as an efficient and reusable catalyst for the synthesis of substituted pyrazolo[3,4-d]pyrimidin-4-ones under solvent-free conditions

A green and efficient method for the synthesis of pyrazolo[3,4-d]pyrimidin- 4-ones through heterocyclization reaction of 5-amino-1-phenyl-1H-pyrazole-4- carboxamides with orthoesters using Montmorillonite K10, as an effective and reusable catalyst, under solventfree conditions is described. The present methodology offers several advantages, such as a simple procedure with an easy work-up, short reaction times, high yields and the absence of any volatile and hazardous organic solvents. Furthermore, the products could be separated simply from the catalyst and the catalyst could be recycled and reused with only slight reduction in its catalytic activity.

Synthesis of pyrazolo[3,4-d]pyrimidin-4-ones catalyzed by Bronsted-acidic ionic liquids as highly efficient and reusable catalysts

A convenient and efficient method for the synthesis of pyrazolo[3,4-d] pyrimidin-4-ones via heterocyclization reaction of 5-amino-1H-pyrazole-4- carboxamides with triethyl orthoesters using two Br?nsted-acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [MIM +(CH2)4SO3H][HSO4 -] or N-(4-sulfonic acid)butyl triethylammonium hydrogen sulfate [Et3N+(CH2)4SO3H] [HSO4-], as efficient homogeneous catalysts under solvent-free conditions is described.

STUDIES ON PYRAZOLOPYRIMIDINE DERIVATIVES. XVIII. FACILE PREPARATION OF 1H-PYRAZOLOPYRIMIDIN-4(5H)-ONES

Reaction of 5-amino-1-phenyl-1H-pyrazole-4-carboxamide (4) with the esters (3a-h) in the presence of sodium ethoxide in ethanol gave 1-phenyl-1H-pyrazolopyrimidin-4(5H)-one (1a) and its 6-substituted derivatives (1b-h).Similar treatment of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (5) with 3a-h gave the 1-methyl-1H-pyrazolopyrimidin-4(5H)-ones (2a-h).