65973-69-5

Basic information

• Product Name: 5-amino-1-(2-nitrophenyl)-1H-pyrazole-4-carbonitrile
• Synonyms: 5-amino-1-(2-nitrophenyl)-1H-pyrazole-4-carbonitrile;5-amino-1-(pyrimidin-2-yl)-1H-pyrazole-4-carbonitrile
• CAS NO: 65973-69-5
• Molecular Formula: C₁₀H₇N₅O₂
• Molecular Weight: 229.19488
• Mol File: 65973-69-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 178℃
• Boiling Point: 493.217 °C at 760 mmHg
• Flash Point: 252.089 °C
• Appearance: /
• Density: 1.51
• CAS DataBase Reference: 5-amino-1-(2-nitrophenyl)-1H-pyrazole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-1-(2-nitrophenyl)-1H-pyrazole-4-carbonitrile(65973-69-5)
• EPA Substance Registry System: 5-amino-1-(2-nitrophenyl)-1H-pyrazole-4-carbonitrile(65973-69-5)

Safety Data

• Hazardous Substances Data: 65973-69-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 20, p. 511, 1983 DOI: 10.1002/jhet.5570200304

Upstream product

• 3034-19-3 (2-nitrophenyl)hydrazine 
• 123-06-8 Ethoxymethylenemalononitrile 
• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 
• 146754-40-7 2-(2-nitrophenylhydrazino)-1,1-ethenedicarbonitrile 
• 6293-87-4 o-nitrophenylhydrazine hydrochloride 
• 88-74-4 2-nitro-aniline 

Downstream Products

• 87121-52-6 N-<4-cyano-1-((2-(1-ethoxy-1-propylidene)amino)phenyl)-1H-pyrazol-5-yl>propanimidic acid ethyl ester 
• 87121-50-4 N-<2-(5-amino-4-cyano-1H-pyrazol-1-yl)phenyl>ethanimidic acid ethyl ester 
• 135108-75-7 4-Amino-1-(2-amino-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 146754-45-2 1-(2-aminophenyl)-5-(pyrrol-1-yl)pyrazole-4-carbonitrile 
• 146754-44-1 1-(2-nitrophenyl)-5-(pyrrol-1-yl)pyrazole-4-carboxylic acid 
• 146754-43-0 1-(2-nitrophenyl)-5-(pyrrol-1-yl)pyrazole 
• 16459-42-0 5-amino-1-(2-nitrophenyl)pyrazole 
• 87138-51-0 5-amino-1-(2-aminophenyl)-1H-pyrazole-4-carbonitrile 
• 135108-60-0 4-Amino-5-methyl-1-(2-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 146754-41-8 1-(2-nitrophenyl)-5-(pyrrol-1-yl)pyrazole-4-carbonitrile 

Relevant articles and documents

6-Arylmethyl-substituted pyrazolopyrimidines

The invention relates to novel 6-arylmethyl-substituted pyrazolopyrimidines, process for their preparation and their use for producing medicaments for improving perception, concentration, learning and/or memory.

6-CYCLYLMETHYL- AND 6-ALKYLMETHYL-SUBSTITUTED PYRAZOLOPYRIMIDINES

The invention relates to novel 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines, method for production and use thereof for the production of medicaments for the improvement of cognition, concentration, learning and/or memory capacity.

Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine

Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents were examined. All compounds were tested for A1 adenosine receptor affinity by using a (R)-[3H]-N6-(phenylisopropyl)adenosine binding assay. The 3-chlorophenyl group showed the greatest activity in the N1-position and the butyl group produced the greatest activity in the N5-position. Combination of the best substituent in each of these positions enhanced the overall activity. The most potent compound was 4-amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one with an IC50 of 6.4 X 10-6 M. Selectivity at the receptor subclasses was examined by performing an A2 adenosine receptor affinity assay with [3H]CGS 21680. This series of compounds were slightly less potent at A2 receptors. 4-Amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one was the most potent compound with an IC50 of 19.2 X 10-6 M.