• 1. Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy?
  Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
• 2. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
• 3. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 4. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 5. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126

Introduction to 5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde (CAS No. 370561-61-8)

5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde, with the chemical identifier CAS No. 370561-61-8, is a compound of significant interest in the field of pharmaceutical chemistry and medicinal research. This heterocyclic aldehyde features a pyrazole core substituted with chloro and methyl groups, making it a versatile scaffold for the development of bioactive molecules. The structural motif of this compound has garnered attention due to its potential pharmacological properties, particularly in the context of targeting inflammatory and immunomodulatory pathways.

The pyrazole ring is a well-documented pharmacophore in drug discovery, known for its ability to interact with various biological targets such as enzymes and receptors. The presence of chlorine atoms at the 5-position and 2-position of the phenyl ring enhances the electrophilicity of the aldehyde group at the 4-position, facilitating further functionalization through condensation reactions with nucleophiles. This reactivity makes 5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde a valuable intermediate in synthesizing more complex molecules.

In recent years, there has been growing interest in developing small-molecule inhibitors that modulate inflammatory responses by targeting key enzymes such as cyclooxygenases (COX) and lipoxygenases (LOX). The pyrazole scaffold, with its ability to engage in hydrogen bonding and hydrophobic interactions, is particularly suited for designing such inhibitors. Studies have demonstrated that derivatives of pyrazole can exhibit potent anti-inflammatory activity by inhibiting the production of pro-inflammatory mediators.

Moreover, the chloro substituents in this compound contribute to its lipophilicity, which is often a critical factor in drug absorption and distribution. The methyl group at the 3-position further influences the electronic properties of the pyrazole ring, potentially enhancing its binding affinity to biological targets. These structural features make 5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde an attractive candidate for further exploration in medicinal chemistry.

Recent advancements in computational chemistry have enabled researchers to predict the binding modes of small molecules to biological targets with high accuracy. Molecular docking studies have been performed using 5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde as a lead compound to identify potential binding interactions with enzymes such as COX-2 and LOX enzymes. These studies have revealed that the aldehyde group can form hydrogen bonds with key residues in the active site, while the chloro and methyl substituents contribute to hydrophobic interactions.

The synthesis of 5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde involves multi-step organic transformations, starting from readily available precursors such as chlorobenzene derivatives and malononitrile. The introduction of chlorine atoms into the phenyl ring is typically achieved through electrophilic aromatic substitution reactions, while the pyrazole core is constructed via condensation reactions between hydrazine derivatives and α-haloketones. The final step involves formylation at the 4-position, which can be accomplished using reagents such as phosphorus oxychloride (POCl?) or dimethylformamide (DMF) in the presence of a Lewis acid catalyst.

In conclusion, 5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde represents a promising scaffold for developing novel therapeutic agents targeting inflammatory diseases. Its unique structural features, including the presence of chloro and methyl substituents, make it a versatile intermediate for further chemical modifications. Ongoing research efforts are focused on optimizing its pharmacological properties through structure-based drug design and high-throughput screening techniques.

• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)