87412-84-8

Basic information

• Product Name: 4-amino-3-methyl-1-phenylpyrazolo<3,4-d>pyrimidine
• Synonyms: 4-amino-3-methyl-1-phenylpyrazolo<3,4-d>pyrimidine
• CAS NO: 87412-84-8
• Molecular Weight: 225.253
• Mol File: 87412-84-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-amino-3-methyl-1-phenylpyrazolo<3,4-d>pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-3-methyl-1-phenylpyrazolo<3,4-d>pyrimidine(87412-84-8)
• EPA Substance Registry System: 4-amino-3-methyl-1-phenylpyrazolo<3,4-d>pyrimidine(87412-84-8)

Safety Data

• Hazardous Substances Data: 87412-84-8(Hazardous Substances Data)

Upstream product

• 77287-34-4 formamide 
• 5346-56-5 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile 
• 5417-82-3 (1-ethoxyethylidene)malononitrile 
• 100-63-0 phenylhydrazine 
• 14247-06-4 ethyl N-(4-cyano-3-methyl-1-phenyl-1H-pyrazol-5-yl)formimidate 
• 1187-11-7 acetylmalonodinitrile 
• 5515-16-2 2-(methoxyethylidene)propanedinitrile 

Downstream Products

• 52217-39-7 1-phenyl-3-methylpyrazolo<3,4-d>pyrimidine 
• 87412-87-1 3-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 87412-80-4 1-phenyl-3-methyl-4-(m-anisyl)pyrazolo<3,4-d>pyrimidine 
• 87412-81-5 1-phenyl-3-methyl-4-(o-anisyl)pyrazolo<3,4-d>pyrimidine 
• 87412-95-1 5-(3-methyl-1-phenyl-4-pyrazolyl)-3-phenyl-1,2,4-oxadiazole 
• 87412-91-7 1-phenyl-3-methyl-4-(pentyloxy)-1H-pyrazolo<3,4-d>pyrimidine 
• 1454788-99-8 6-cyano-7-imino-3,5-dimethyl-N¹-phenyl-1, 7-dihydropyrazolo[3', 4':4, 5]pyrimido[1, 6-a]pyrimidine 
• 1454789-03-7 ethyl 3,5-dimethyl-7-imino-N¹-phenyl-1,7-dihydropyrazolo[3',4':4,5]pyrimido[1,6-a]pyrimidine-6-carboxylate 
• 1454789-04-8 ethyl 5-ethyl-7-imino-3-methyl-N¹-phenyl-1,7-dihydropyrazolo[3',4':4,5]pyrimido[1,6-a]pyrimidine-6-carboxylate 
• 1454788-98-7 6-cyano-7-imino-3-methyl-N¹-phenyl-1,7-dihydropyrazolo[3',4':4,5]pyrimido[1,6-a]pyrimidine 
• 1448550-32-0 C₂₆H₂₅N₇O₂ 
• 1448550-33-1 C₂₄H₂₃N₇O₂ 
• 1448550-30-8 C₂₇H₂₈N₆O 
• 1448550-29-5 C₂₅H₂₆N₆O 

Relevant articles and documents

1,3-disubstituted-4-aminopyrazolo [3, 4-d] pyrimidines, a new class of potent inhibitors for phospholipase D

Phospholipase D enzymes cleave lipid substrates to produce phosphatidic acid, an important precursor for many essential cellular molecules. Phospholipase D is a target to modulate cancer-cell invasiveness. This study reports synthesis of a new class of phospholipase D inhibitors based on 1,3-disubstituted-4-amino-pyrazolopyrimidine core structure. These molecules were synthesized and used to perform initial screening for the inhibition of purified bacterial phospholipase D, which is highly homologous to the human PLD1. Initially tested with the bacterial phospholipase D enzyme, then confirmed with the recombinant human PLD1 and PLD2 enzymes, the molecules presented here exhibited inhibition of phospholipase D activity (IC50) in the low-nanomolar to low-micromolar range with both monomeric substrate diC4PC and phospholipid vesicles and micelles. The data strongly indicate that these inhibitory molecules directly block enzyme/vesicle substrate binding. Preliminary activity studies using recombinant human phospholipase Ds in in vivo cell assays measuring both transphosphatidylation and head-group cleavage indicate inhibition in the mid- to low-nanomolar range for these potent inhibitory novel molecules in a physiological environment. This study reports synthesis of a new class of PLD inhibitors based on 1,3-disubstituted-4-amino-pyrazolopyrimidine core structure. These molecules exhibited inhibition of human recombinant PLD activity (IC 50) in the low-nanomolar to low-micromolar range with monomeric substrate diC4PC and phospholipid vesicles and micelles. Preliminary activity studies using recombinant human PLDs in in vivo cell assays measuring both transphosphatidylation and head-group cleavage indicates inhibition in the mid- to low-nanomolar range for these potent inhibitory novel molecules in a physiological environment.

Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives

3-Substituted-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines 2a-c were synthesized by treating 5-aminopyrazole- 4-carbonitriles 1a-c with formamide. The reactivity of compounds 1a-c towards some cyclic anhydrides was studied. The condensation of 5-aminopyrazole-4-carbonitrile 1b with triethylorthoformate gives imidate 7b, which reacts with a series of primary amines and leads to pyrazolo[3,4-d]pyrimidine-4-amines 9 and 10. The reaction of imidate 7b with ammonia and hydroxylamine afforded pyrazolopyrimidine 2b and pyrazolo[3,4-d]pyrimidin-5-(4H) -ol 11, respectively. The synthesized compounds were completely characterized by 1H NMR, 13C NMR, IR, and HRMS. The antibacterial activity of some new synthesized compounds was evaluated and appeared to be signiflcant. Tubitak.

Synthesis and antifungal activity of pyrazolo[3,4-d]pyrimidin-4(5H)-thiones

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