58791-82-5

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-1-(4-CHLOROPHENYL)-3-METHYL-1H-PYRAZOLE-4-CARBONITRILE is used as a potential active pharmaceutical ingredient for the development of new drugs, leveraging its unique chemical structure and pharmacological properties.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 5-AMINO-1-(4-CHLOROPHENYL)-3-METHYL-1H-PYRAZOLE-4-CARBONITRILE serves as a valuable compound for studying its interactions with biological targets, which may lead to the discovery of novel therapeutic agents.
Used in Drug Design and Optimization:
5-AMINO-1-(4-CHLOROPHENYL)-3-METHYL-1H-PYRAZOLE-4-CARBONITRILE is utilized as a starting point for drug design and optimization processes, where its structure can be modified to enhance its pharmacological activity, selectivity, and safety profile.
Used in Drug Synthesis:
As a key intermediate in the synthesis of various pharmaceutical compounds, 5-AMINO-1-(4-CHLOROPHENYL)-3-METHYL-1H-PYRAZOLE-4-CARBONITRILE plays a crucial role in the development of new drug candidates with improved therapeutic potential.
Used in Drug Discovery:
5-AMINO-1-(4-CHLOROPHENYL)-3-METHYL-1H-PYRAZOLE-4-CARBONITRILE is employed in high-throughput screening assays and other drug discovery techniques to identify its potential as a lead compound for the treatment of various diseases and conditions.

Upstream product

• 63917-11-3 (ethoxyethylidene)malononitrile 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 5417-82-3 (1-ethoxyethylidene)malononitrile 

Downstream Products

• 1015765-78-2 1-(4-chlorophenyl)-3-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxylic acid 

Relevant academic research and scientific papers

Pyrazolyl-tetrazoles and imidazolyl-pyrazoles as potential anticoagulants and their integrated multiplex analysis virtual screening

This article reports a novel virtual screening algorithm seeking the rational identification of novel lead anticoagulants. Seven 5-(3-methyl-1-aryl-1H-pyrazol-4-yl)-1H-tetrazoles and seven novel 1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-3-methyl-1H-pyrazole

Synthesis and activity of novel tetrazole compounds and their pyrazole-4-carbonitrile precursors against Leishmania spp

A new series of 5-(1-aryl-3-methyl-1H-pyrazol-4-yl)-1H-tetrazole derivatives (4a-m) and their precursor 1-aryl-3-methyl-1H-pyrazole-4- carbonitriles (3a-m) were synthesized and evaluated as antileishmanials against Leishmania braziliensis and Leishmania amazonensis promastigotes in vitro. In parallel, the cytotoxicity of these compounds was evaluated on the RAW 264.7 cell line. The results showed that among the assayed compounds the substituted 3-chlorophenyl (4a) (IC50/24 h = 15 ± 0.14 μM) and 3,4-dichlorophenyl tetrazoles (4d) (IC50/24 h = 26 ± 0.09 μM) were the most potent against L. braziliensis promastigotes, as compared the reference drug pentamidine, which presented IC50 = 13 ± 0.04 μM. In addition, 4a and 4d derivatives were less cytotoxic than pentamidine. However, these tetrazole derivatives (4) and pyrazole-4- carbonitriles precursors (3) differ against each of the tested species and were more effective against L.braziliensis than on L. amazonensis.

Synthesis, cannabinoid receptor affinity, and molecular modeling studies of substituted 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides

The new 1-phenyl-5-(1H-pyrrol-1-yl)pyrazole-3-carboxamides were compared with the reference compounds AM251 and SR144528 for cannabinoid hCB1 and hCB2 receptor affinity. Compounds bearing 2,4-dichlorophenyl or 2,4-difluorophenyl groups at position 1 and 2,5-dimethylpyrrole moiety at position 5 of the pyrazole nucleus were generally more selective for hCB 1. On the other hand, the N-cyclohexyl group at the 3-carboxamide was the determinant for the hCB2 selectivity, in particular when a 3,4-dichlorophenyl group was also present at position 1. Compound 26 was the most selective ligand for the hCB1 receptor (Ki (CB 2)/Ki (CB1) = 140.7). Derivative 30, the most potent hCB1 ligand (Ki = 5.6 nM), was equipotent to AM251 and behaved as an inverse agonist in the cAMP assay (EC50 ～1 nM). The carbonyl oxygen of both 26 and 30 formed a H-bond with K3.28(192), while the substituents at the nitrogen fitted in a pocket formed by lipophilic residues. This H-bonding interaction was proposed to account for the high affinity for receptors' inactive state and the inverse agonist activity.