1225387-53-0

Basic information

• Product Name: 1H-PYRAZOL-5-AMINE
• Synonyms: AKOS PAO-0255;1H-PYRAZOL-5-AMINE;2H-Pyrazol-3-amine
• CAS NO: 1225387-53-0
• Molecular Formula: C₃H₅N₃
• Molecular Weight: 83.0919
• Mol File: 1225387-53-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 1H-PYRAZOL-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-PYRAZOL-5-AMINE(1225387-53-0)
• EPA Substance Registry System: 1H-PYRAZOL-5-AMINE(1225387-53-0)

Safety Data

• Hazardous Substances Data: 1225387-53-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
1H-PYRAZOL-5-AMINE is used as a pharmaceutical intermediate for its anti-inflammatory and analgesic properties, making it a valuable component in the development of new medications aimed at treating pain and inflammation.
Used in Organic Compound Synthesis:
1H-PYRAZOL-5-AMINE is used as a building block in the synthesis of various organic compounds, contributing to the creation of a diverse range of chemical products.
Used in Agrochemical Production:
1H-PYRAZOL-5-AMINE is used as a precursor in the production of agrochemicals, playing a crucial role in the development of substances that protect crops and enhance agricultural productivity.
Used in Materials Science:
1H-PYRAZOL-5-AMINE is used in the field of materials science for its potential applications in the development of organic light-emitting diodes (OLEDs) and other electronic devices, showcasing its versatility beyond pharmaceutical and chemical applications.

Upstream product

• 26621-44-3 5-nitro-1H-pyrazole 
• 6162-76-1 cyanoacetaldehyde 
• 2407-68-3 3-dimethylaminoacrylonitrile 
• 75-05-8 acetonitrile 
• 109-94-4 formic acid ethyl ester 
• 106087-63-2 6-Nitro-4H-pyrazolo[1,5-a]pyrimidin-7-one 
• 3994-46-5 N-aminopyrazole 

Downstream Products

• 29274-35-9 5-methyl-4H-pyrazolo<1,5-a>pyrimidin-7-one 
• 133549-59-4 6-Cyclohexyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione 
• 54408-76-3 5-amino-pyrazole-1-carboxylic acid methylamide 
• 54408-75-2 3-Amino-1-methylcarbamoyl-pyrazol 
• 126352-69-0 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine 
• 244127-30-8 5-ethyl-4H-pyrazolo<1,5-a>pyrimidin-7-one 
• 802983-90-0 5,7-diphenylpyrazolo[1,5-a]pyrimidine 
• 29274-23-5 4,7-dihydropyrazolo<1,5-a>pyrimidin-7-one 
• 29274-22-4 4H,5H-pyrazolo[1,5-a]pyrimidine-5-one 

Relevant articles and documents

The metabolism of a series of ester pro-drugs by NCTC 2544 cells, skin homogenate and LDE testskin

The metabolism of a series of substituted pyrazolopyridine ester pro-drugs was investigated using NCTC 2544 cells, human skin homogenate and LDE Testskin as model systems. The compounds were incubated in each system and the disappearance of drug and the production of the major hydrolysis product was observed with time and quantitated using HPLC. The toxicity of the ester pro-drugs and the metabolites was examined in NCTC 2544 cells using a cell viability assay procedure. Hydrolytic activity was slightly higher in the cell culture model than in skin homogenate solution but the rank order of activity for each pro-drug was similar. The metabolic activity of LDE Testskin was much reduced compared with the other systems, but again the overall pattern of metabolism was not dissimilar. These findings indicate that NCTC 2544 cells provide a reasonable model for human skin ester hydrolysis both in terms of rate and in terms of substrate specificity.

Discovery and characterization of a novel 7-aminopyrazolo[1,5-a]pyrimidine analog as a potent hepatitis C virus inhibitor

We describe a novel 7-aminopyrazolo[1,5-a]pyrimidine (7-APP) derivative as a potent hepatitis C virus (HCV) inhibitor. A series of 7-APPs was synthesized and evaluated for inhibitory activity against HCV in different cell culture systems. The synthesis and preliminary structure-activity relationship study of 7-APP are reported.

Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors

A structure-activity relationship study of dorsomorphin, a previously identified inhibitor of SMAD 1/5/8 phosphorylation by bone morphogenetic protein (BMP) type 1 receptors ALK2, 3, and 6, revealed that increased inhibitory activity could be accomplished by replacing the pendent 4-pyridine ring with 4-quinoline. The activity contributions of various nitrogen atoms in the core pyrazolo[1,5-a]pyrimidine ring were also examined by preparing and evaluating pyrrolo[1,2-a]pyrimidine and pyrazolo[1,5-a]pyridine derivatives. In addition, increased mouse liver microsome stability was achieved by replacing the ether substituent on the pendent phenyl ring with piperazine. Finally, an optimized compound 13 (LDN-193189 or DM-3189) demonstrated moderate pharmacokinetic characteristics (e.g., plasma t1/2 = 1.6 h) following intraperitoneal administration in mice. These studies provide useful molecular probes for examining the in vivo pharmacology of BMP signaling inhibition.

Pyrazolo[1,5-a]pyrimidines as orally available inhibitors of cyclin-dependent kinase 2

Properly substituted pyrazolo[1,5-a]pyrimidines are potent and selective CDK2 inhibitors. Compound 15j is orally available and showed efficacy in a mouse A2780 xenograft model.

NITROAZINES. 15. CONTRACTION OF THE PYRIMIDINE RING IN 6-NITROAZOLOPYRIMIDINES

It is shown that contraction of the pyrimidine ring occurs when 6-nitro-7-oxo-4,7-dihydroazolopyrimidines are heated with hydrazine hydrate.Complexes of 4-nitropyrazole with 5-aminoazoles, the structures of which were proved by x-ray diffraction analysis, are formed in a similar reaction of nitrosubstituted azolopyrimidines that do not contain an oxo function.

Rearrangement of 1-Amino- and 1-Alkylamino-pyrazoles to 5-Aminopyrazoles

Rearrangement of 1-aminopyrazole and 1-alkylaminopyrazoles into the corresponding 5-aminopyrazoles has been achieved in 48percent aqueous hydrobromic acid.The reaction, occurring through a ring opening-ring closure mechanism, constitutes a new and unambiguous procedure for the preparation of 1-substituted 5-aminopyrazoles.The products have been identified on the basis of 1H and 13C n.m.r. spectroscopic results and comparison with authentic samples.