87412-87-1

Upstream product

• 87412-84-8 4-amino-3-methyl-1-phenylpyrazolo<3,4-d>pyrimidine 
• 100-66-3 methoxybenzene 
• 100-63-0 phenylhydrazine 
• 64-18-6 formic acid 
• 5346-56-5 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile 
• 122-51-0 orthoformic acid triethyl ester 
• 50427-81-1 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid amide 

Downstream Products

• 205753-30-6 4-chloro-3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 204520-34-3 (4-Methoxy-phenyl)-(3-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 

Relevant academic research and scientific papers

Synthesis of aminocyanopyrazoles via a multi-component reaction and anti-carbonic anhydrase inhibitory activity of their sulfamide derivatives against cytosolic and transmembrane isoforms

A convenient protocol for the multicomponent reaction (MCRs) between malononitrile with an orthoester and hydrazine derivatives, under acid catalyst is described. A series of aminocyanopyrazoles 4 was prepared, isolated and characterized. These pyrazoles reacted with sodium nitrite followed by secondary amine reagent and with formic acid to lead pyrazolotriazines 6 and pyrazolopyrimidinones 7. Some of the aminopyrazoles were converted to the corresponding sulfamides by reaction with sulfamoyl chloride. The aminopyrazoles incorporating phenyl and tosyl moieties were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the human (h) hCA I, II, IX and XII. Many of them showed low micromolar or submicromolar inhibition of these enzymes. The corresponding sulfamides were low nanomolar CA inhibitors.

Design and synthesis of pyrazolo[3,4-d]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma

A new series of pyrazolo[3,4-d]pyrimidines tethered with nitric oxide (NO) producing functionality was designed and synthesized. Sulforhodamine B (SRB) protein assay revealed that NO releasing moiety in the synthesized compounds significantly decreased the cell growth more than the des-NO analogues. Compounds 7C and 7G possessing N-para-substituted phenyl group, released the highest NO concentration of 4.6% and 4.7% respectively. Anti-proliferative activity of synthesized compounds on HepG2 cell line identified compounds 7h, 7p, 14a and 14b as the most cytotoxic compounds in the series of IC50?=?3, 5, 3 and 5?μM, respectively, compared to erlotinib as a reference drug (IC50?=?25?μM). Flow cytometry studies revealed that 7?h arrested the cells in G0/G1 phase of cell cycle while 7p arrested the cells in S phase. Moreover, docking study of the synthesized compounds on EGFR (PDB code: 1M17) and cytotoxicity study indicated that N-1 phenyl para substitution, pyrazole C-3 alkyl substitution and tethering the nitrate moiety through butyl group had a significant impact on the activity.

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.

Aryl Coupling Reactions of Pyrazolopyrimidin-4-yl Radicals

4-Arylpyrazolopyrimidines (4) were the subjects of a synthetic investigation in order to evaluate their biological activity.Attempts to prepare 4 from 4-aminopyrazolopyrimidines (5) via classical Gomberg-Bachmann-Hey aryl coupling conditions failed.Conversion of 5 to 4 was accomplished by diazotiazation of 5 using alkyl nitrites with an acid catalyst in aromatic solvents.Isomer distribution of the aryl-coupled products 4 was that predicted for a radical intermediate (ortho > meta ca. para); isomer structures were assigned by a detailed 1H NMR analysis.Unusual fragmentation products 17 and 18 were isolated during the course of investigations.These oxadiazoles probably arise from collapse of intermediate pyrazolopyrimidin-4-yl radicals 15.