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  Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
• 2. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Phenylpyrazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Phenylpyrazoles

Introduction to 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid (CAS No. 14678-90-1)

5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid, identified by its Chemical Abstracts Service (CAS) number 14678-90-1, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the pyrazole class, a scaffold widely recognized for its biological activity and structural versatility. The presence of both amino and carboxylic acid functional groups, coupled with a chlorophenyl substituent, makes it a promising candidate for further exploration in drug discovery and development.

The pyrazole core is a six-membered aromatic ring containing two adjacent nitrogen atoms, which contributes to its unique electronic properties and reactivity. This structural motif is extensively studied due to its role in numerous biologically active molecules, including antiviral, antibacterial, anti-inflammatory, and anticancer agents. The specific substitution pattern in 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid enhances its potential as a pharmacophore, enabling interactions with various biological targets.

In recent years, there has been a surge in research focused on developing novel heterocyclic compounds with therapeutic potential. The chlorophenyl group at the 1-position of the pyrazole ring introduces electrophilic characteristics, facilitating further derivatization and functionalization. This allows chemists to modify the compound’s properties, such as solubility, bioavailability, and target specificity, making it adaptable for diverse pharmacological applications.

The carboxylic acid moiety at the 4-position provides an acidic character to the molecule, enabling salt formation and enhancing its solubility in aqueous environments. This property is particularly advantageous for formulation development, as it allows for better integration into drug delivery systems. Additionally, the amino group at the 5-position can serve as a site for further chemical modifications, such as coupling with other pharmacophores or forming amide bonds.

One of the most compelling aspects of 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid is its potential in modulating biological pathways associated with diseases. Current research indicates that this compound may exhibit inhibitory effects on enzymes and receptors involved in cancer progression, inflammation, and metabolic disorders. For instance, studies have suggested that pyrazole derivatives can interfere with kinases and other signaling proteins that are aberrantly activated in tumor cells.

Recent advancements in computational chemistry have enabled researchers to predict the binding affinity of this compound to various protein targets with high accuracy. Molecular docking simulations have identified potential interactions with enzymes such as cyclooxygenase (COX), which is implicated in pain and inflammation, as well as proteases involved in cancer cell proliferation. These findings provide a strong rationale for further investigation into the pharmacological properties of 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid.

The synthesis of this compound typically involves multi-step organic reactions starting from readily available precursors. The chlorination step at the phenyl ring is a critical step that introduces the electrophilic center necessary for subsequent functionalization. Advanced synthetic methodologies have been developed to improve yield and purity, ensuring that the final product meets pharmaceutical standards.

In preclinical studies, 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid has demonstrated promising results in cell-based assays. Its ability to inhibit specific enzymatic activities has led to investigations into its potential as an antitumor agent. Additionally, its structural features have been leveraged to develop analogs with enhanced potency and selectivity. These findings underscore the importance of heterocyclic compounds like pyrazoles in modern drug discovery.

The development of novel therapeutic agents requires not only potent activity but also favorable pharmacokinetic profiles. The solubility provided by the carboxylic acid group enhances oral bioavailability, making this compound an attractive candidate for clinical translation. Furthermore, its stability under various conditions ensures compatibility with formulation processes used in drug manufacturing.

As research continues to uncover new biological targets and mechanisms of disease, compounds like 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid will play an increasingly important role in therapeutic innovation. The combination of structural versatility and demonstrated biological activity positions this molecule as a valuable tool for both academic researchers and pharmaceutical companies seeking to develop next-generation treatments.

The future direction of research on this compound may include exploring its potential in combination therapies alongside other drugs that target different pathways. Such approaches could lead to synergistic effects that enhance treatment outcomes while minimizing side effects. Additionally, investigating its role in precision medicine—where treatments are tailored to individual patient profiles—could open new avenues for clinical application.

• 15070-84-5(5-Amino-1-(3-chlorophenyl)-1H-pyrazole-4-carboxylic Acid)
• 14678-87-6(Ethyl 5-amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate)
• 51649-80-0(5-Amino-1-phenyl-1H-pyrazole-4-carboxylic acid)
• 1253791-51-3(Ethyl 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carboxylate hydrochloride)
• 1225550-72-0(5-Amino-1-(2,3-dichlorophenyl)-1H-Pyrazole-4-carboxylic acid)
• 14678-93-4(5-Amino-1-(4-Methylphenyl)-1h-Pyrazole-4-Carboxylic Acid)
• 15001-08-8(Ethyl 5-amino-1-(3-chlorophenyl)-1H-pyrazole-4-carboxylate)
• 225930-54-1(Ethyl 3-amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate)
• 14678-89-8(5-Amino-1-(2-chlorophenyl)-1h-pyrazole-4-carboxylic acid)
• 77746-66-8(1H-Pyrazole-4-carboxaldehyde, 5-amino-1-(4-chlorophenyl)-)