5334-31-6

Basic information

• Product Name: 3-Amino-1H-pyrazole-4-carboxamide
• Synonyms: 3-AMINOPYRAZOLE-4-CARBOXAMIDE;3-AMINO-PYRAZOLE-4-CARBOXYLIC ACID AMIDE;5-Amino-1H-pyrazole-4-carboxylic amide;3-Amino-1H-pyrazole-4-carboxamide;5-azanyl-1H-pyrazole-4-carboxamide;5-Amino-1H-pyrazole-4-car...;3-AMino-1H-pyrazole-4-car...;3-AMino-1H-pyrazole-4-carboxylic aMide
• CAS NO: 5334-31-6
• Molecular Formula: C₄H₆N₄O
• Molecular Weight: 126.12
• EINECS: 226-252-3
• Mol File: 5334-31-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 187-189 °C(Solv: water (7732-18-5))
• Boiling Point: 454.3°Cat760mmHg
• Flash Point: 228.5°C
• Appearance: /
• Density: 1.538g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Very Slightly)
• PKA: 13.26±0.50(Predicted)
• CAS DataBase Reference: 3-Amino-1H-pyrazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-1H-pyrazole-4-carboxamide(5334-31-6)
• EPA Substance Registry System: 3-Amino-1H-pyrazole-4-carboxamide(5334-31-6)

Safety Data

• Hazardous Substances Data: 5334-31-6(Hazardous Substances Data)

Usage

Description

3-Amino-1H-pyrazole-4-carboxamide is an organic compound with the molecular formula C4H5N5O. It is a heterocyclic compound featuring a pyrazole ring and a carboxamide functional group. This molecule is known for its potential applications in the pharmaceutical and chemical industries due to its unique structure and reactivity.

Uses

Used in Pharmaceutical Industry:
3-Amino-1H-pyrazole-4-carboxamide is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its application is primarily due to its ability to be incorporated into more complex molecular structures, which can exhibit therapeutic properties.
Used in Synthesis of Anticancer Agents:
3-Amino-1H-pyrazole-4-carboxamide is used as a building block for the synthesis of 4H-3,1-Benzothiazinone analogs, which have demonstrated antiproliferative activity against human cancer cell lines. This application takes advantage of the compound's reactivity and potential to be part of a larger, bioactive molecule.
Used in Synthesis of Allopurinol Impurities:
3-Amino-1H-pyrazole-4-carboxamide is also utilized as an intermediate in the synthesis of 3-(4H-1,2,4-Triazol-4-yl)-1H-pyrazole-4-carboxamide (T767570), which is an impurity of Allopurinol (A547300). Allopurinol is a xanthine oxidase inhibitor that decreases uric acid production and is used in the treatment of hyperuricemia and chronic gout. 3-Amino-1H-pyrazole-4-carboxamide's role in this process highlights its importance in the development of therapeutic agents for gout management.
Used in Treatment of Hyperuricemia and Chronic Gout:
As a component in the synthesis of Allopurinol, 3-Amino-1H-pyrazole-4-carboxamide indirectly contributes to the treatment of hyperuricemia and chronic gout. Its involvement in the production of a medication that helps manage these conditions underscores its utility in the pharmaceutical sector.

InChI:InChI=1/C4H6N4O/c5-3-2(4(6)9)1-7-8-3/h1H,(H2,6,9)(H3,5,7,8)

Upstream product

• 16617-46-2 3-amino-4-cyano-2H-pyrazole 
• 16617-46-2 3-Amino-4-cyanopyrazole 

Downstream Products

• 139954-41-9 6-(4-Chloro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 43024-19-7 5,7-dimethylpyrazolo<1,5-a>pyrimidine-8-carboxamide 
• 115930-94-4 7-Phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 24521-76-4 4-hydroxy-6-mercapto-1H-pyrazolo[3,4-d]pyrimidine 
• 2465-59-0 oxypurinol 

Relevant articles and documents

Quantitative analysis and alkaline stability studies of allopurinol.

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Synthesis, anticancer evaluation, and molecular docking studies of some novel 4,6-disubstituted pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 (CDK2) inhibitors

A novel series of 4,6-disubstituted pyrazolo[3,4-d]pyrimidines (7–43) bearing various anilines at C-4 position and thiophenethyl or thiopentane moieties at C-6 position have been designed and synthesized by molecular hybridization approach. All the synthesized compounds were evaluated for in vitro CDK2/cyclin E and Abl kinase inhibitory activity as well as anti-proliferative activity against K-562 (chronic myelogeneous leukemia), and MCF-7 (breast adenocarcinoma) cell lines. The structure–activity relationship (SAR) studies revealed that compounds with thiophenethyl group at C-6 with mono-substituted anilines at C-4 exhibited better CDK2 inhibitory activity compared to alkyl group (thiopentane) at C-6 and di-substituted anilines at C-4 of the scaffold. In particular, compounds having 2-chloro, 3-nitro and 4-methylthio aniline groups at C-4 displayed significant enzymatic inhibitory activity against CDK2 with single digit micromolar IC50 values. The in silico molecular docking studies suggested possible binding orientation and the binding energies were in agreement with the observed SAR as well as experimental results. In addition, some of the synthesized compounds showed anti-proliferative effects against K-562 and MCF-7 cancer cell lines with IC50 values in a micromolar range. Thus, the synthesized compounds could be considered as new anticancer hits for further lead optimization.

Oxadiazole derivatives as a novel class of antimitotic agents: Synthesis, inhibition of tubulin polymerization, and activity in tumor cell lines

Oxadiazole derivatives were synthesized and evaluated for their ability to inhibit tubulin polymerization and to cause mitotic arrest in tumor cells. The most potent compounds inhibited tubulin polymerization at concentrations below 1 μM. Lead analogs caused mitotic arrest of A431 human epidermoid cells and cells derived from multi-drug resistant tumors (10, EC50 = 7.8 nM). Competition for the colchicine binding site and pharmacokinetic properties of selected potent compounds were also investigated and are reported herein, along with structure-activity relationships for this novel series of antimitotic agents.