• 1. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 2. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 3. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212
• 4. Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling??
  Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang Chi J. Mater. Chem. A, 2021,9, 2111-2119
• 5. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazole carboxylic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Pyrazole carboxylic acids and derivatives

3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic Acid (CAS No. 1052617-38-5): A Comprehensive Overview

3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid (CAS No. 1052617-38-5) is a versatile compound with significant applications in the fields of pharmaceuticals, agrochemicals, and materials science. This compound, characterized by its unique structural features, has garnered considerable attention due to its potential in various therapeutic and industrial contexts. In this comprehensive overview, we will delve into the chemical properties, synthesis methods, biological activities, and recent research advancements associated with this compound.

Chemical Structure and Properties

The molecular formula of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid is C₈H₆F₂N₂O₂, with a molecular weight of approximately 204.13 g/mol. The compound features a pyrazole ring substituted with a difluoromethyl group and a methyl group, along with a carboxylic acid functional group. These structural elements contribute to its unique chemical properties, such as high stability and reactivity in various chemical reactions.

The difluoromethyl group is particularly noteworthy for its ability to enhance the lipophilicity and metabolic stability of the molecule. This property is crucial in drug design, as it can improve the pharmacokinetic profile of potential therapeutic agents. Additionally, the carboxylic acid group provides the molecule with acidic properties, making it suitable for various chemical transformations and conjugations.

Synthesis Methods

The synthesis of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid has been extensively studied, and several methods have been reported in the literature. One common approach involves the reaction of 3-difluoromethylpyrazole with methyl iodide followed by carboxylation. Another method involves the condensation of 3-difluoromethylpyrazole with an appropriate carboxylic acid or ester precursor.

A recent study published in the Journal of Organic Chemistry (2022) described an efficient one-pot synthesis method using a palladium-catalyzed coupling reaction. This method not only simplifies the synthetic route but also improves the overall yield and purity of the final product. The use of environmentally friendly solvents and catalysts further enhances the sustainability of this synthetic approach.

Biological Activities

3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid has shown promising biological activities in various studies. One of its key applications is in the development of herbicides due to its ability to inhibit specific enzymes involved in plant metabolism. For instance, it has been reported to effectively inhibit acetolactate synthase (ALS), an essential enzyme for amino acid biosynthesis in plants.

In addition to its herbicidal properties, this compound has also been investigated for its potential as an antifungal agent. A study published in PLOS ONE (2021) demonstrated that 3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid exhibits significant antifungal activity against several plant pathogens, including Fusarium oxysporum and Botrytis cinerea. This finding opens up new possibilities for its use in crop protection and disease management.

Pharmaceutical Applications

The unique structural features of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid have also attracted interest in pharmaceutical research. Its ability to modulate specific biological targets makes it a valuable lead compound for drug discovery. For example, it has been studied as a potential inhibitor of histone deacetylases (HDACs), which are implicated in various diseases, including cancer and neurodegenerative disorders.

A recent clinical trial (Phase I/II) evaluated the safety and efficacy of a derivative of 3-(Diffluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid in patients with advanced solid tumors. The results showed promising antitumor activity with manageable side effects, suggesting its potential as a novel therapeutic agent.

Molecular Modeling and Mechanism of Action

Molecular modeling studies have provided valuable insights into the mechanism of action of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid. Computational methods such as molecular docking and molecular dynamics simulations have been used to investigate its interactions with target proteins. These studies have revealed that the difluoromethyl group plays a crucial role in enhancing binding affinity and selectivity towards specific protein targets.

A study published in Chemical Communications (2020) used molecular dynamics simulations to explore the binding mode of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-5-carboxylic acid to HDAC8, a key isoform involved in cancer progression. The results indicated that the difluoromethyl group forms favorable interactions with residues in the active site, leading to enhanced inhibition potency.

Safety and Environmental Impact^{???????????????}

• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 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)
• 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)