59023-32-4

Basic information

• Product Name: 4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE
• Synonyms: 4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE;4-AMINO-1,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE
• CAS NO: 59023-32-4
• Molecular Formula: C₆H₁₀N₄O
• Molecular Weight: 154.17
• Mol File: 59023-32-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 296.6±40.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• PKA: 15.32±0.50(Predicted)
• CAS DataBase Reference: 4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE(59023-32-4)
• EPA Substance Registry System: 4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE(59023-32-4)

Safety Data

• Hazardous Substances Data: 59023-32-4(Hazardous Substances Data)

Upstream product

• 78208-58-9 1,3-dimethyl-4-nitropyrazole-5-carboxamide 
• 5744-56-9 1,3-dimethylpyrazol-5-carboxylic acid 
• 3920-37-4 1,3-dimethyl-4-nitro-1H-pyrazole-5-carboxylic acid 
• 37141-71-2 1,3-dimethyl-4-nitro-1H-pyrazole-5-carbonyl chloride 

Downstream Products

• 104393-35-3 1,3-Dimethyl-5-(4-trifluoromethyl-phenyl)-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-33-1 5-(2,4-Dimethoxy-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-34-2 4-(1,3-dimethyl-7-oxopyrazolo<4,3-d>pyrimidin-5-yl)benzenesulfonic acid 
• 104393-49-9 2,5-Dimethyl-4-(4-methyl-benzoylamino)-2H-pyrazole-3-carboxylic acid amide 
• 104393-48-8 4-(4-Chloro-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-52-4 4-(3,5-Dimethoxy-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-32-0 5-(3,4-Dimethoxy-phenyl)-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-51-3 4-(3,4-Dichloro-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-50-2 4-(2-Methoxy-benzoylamino)-2,5-dimethyl-2H-pyrazole-3-carboxylic acid amide 
• 104393-31-9 1,3-dimethyl-5-phenylpyrazolo<4,3-d>pyrimidin-7-one 
• 104393-46-6 2,5-Dimethyl-4-phenylacetylamino-2H-pyrazole-3-carboxylic acid amide 
• 111770-15-1 CI 943 
• 104393-24-0 1,3-Dimethyl-5-p-tolyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 
• 104393-21-7 5-Benzyl-1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one 

Relevant articles and documents

A hit to lead discovery of novel N-methylated imidazolo-, pyrrolo-, and pyrazolo-pyrimidines as potent and selective mTOR inhibitors

A series of N-7-methyl-imidazolopyrimidine inhibitors of the mTOR kinase have been designed and prepared, based on the hypothesis that the N-7-methyl substituent on imidazolopyrimidine would impart selectivity for mTOR over the related PI3Kα and δ kinases. The corresponding N-Me substituted pyrrolo[3,2-d]pyrimidines and pyrazolo[4,3-d]pyrimidines also show potent mTOR inhibition with selectivity toward both PI3α and δ kinases. The most potent compound synthesized is pyrazolo[4,3-d]pyrimidine 21c. Compound 21c shows a Ki of 2 nM against mTOR inhibition, remarkable selectivity (>2900×) over PI3 kinases, and excellent potency in cell-based assays.

Sildenafil (Viagra(TM)), a potent and selective inhibitor of type 5 CGMP phosphodiesterase with utility for the treatment of male erectile dysfunction

5-(2'-Alkoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-ones, and in particular our preferred compound, sildenafil (VIAGRA(TM)), discovered through a rational drug design programme, are potent and selective inhibitors of the type 5 cGMP phosphodiesterase from both rabbit platelets and human corpus cavernosum. Sildenafil is currently in the clinic for the oral treatment of male erectile dysfunction.

Synthesis and Structure-Activity Relationships of Pyrazolopyrimidin-7-ones as Adenosine Receptor Antagonists

A series of 21 1,3-dialkylpyrazolopyrimidin-7-ones substituted in the 5-position with various phenyl substituents has been synthesized and found to have affinity for the adenosine A1 receptor.The potency pattern due to substituents of the phenyl ring was found to parallel that found in a previously reported 1,3-dialkyl-8-phenylxanthine series.A quantitative structure-activity relationship was developed between these two series that correctly predicted the potencies of six additional 5-substituted pyrazolopyrimidines that were synthesized during the course of the analysis.With use of the correlation as a guide, one additional 5-phenylpyrazolopyrimidine containing a 4amino>sulfonyl substituent to improve aqueous solubility was prepared.On the basis of the high correlation between adenosine binding affinities of analogously substituted xanthines and pyrazolopyrimidines and the close superposition of the heterocyclic rings and substituents that is apparent from molecular models of these two series (Figure 2), it is hypothesized they fit the receptor in an analogous fashion.