3-[(5-Chloro-2-nitrophenyl)phenylamino]-3-oxopropanoic acid ethyl ester
[CAS# 22316-45-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: 3-[(5-Chloro-2-nitrophenyl)phenylamino]-3-oxopropanoic acid ethyl ester
• Synonyms: 5'-Chloro-2'-nitro-N-phenylmalonanilic acid ethyl ester
• Molecular Formula: C₁₇H₁₅ClN₂O₅
• Molecular Weight: 362.76
• CAS Registry Number: 22316-45-6
• EC Number: 244-907-1
• SMILES: CCOC(=O)CC(=O)N(C1=CC=CC=C1)C2=C(C=CC(=C2)Cl)[N+](=O)[O-]

Properties

• Solubility: Practically insoluble (0.015 g/L) (25 °C), Calc.^*
• Density: 1.371±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 83-85 °C^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

^** Hauptmann, Karl H.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

3-[(5-Chloro-2-nitrophenyl)phenylamino]-3-oxopropanoic acid ethyl ester is a chemical compound that has garnered attention due to its potential applications in medicinal chemistry and its role in the development of pharmaceutical agents. The compound belongs to a class of molecules characterized by the presence of a phenylamino group, which is known to impart significant biological activity. The synthesis of this compound emerged from research aimed at creating new derivatives with enhanced therapeutic properties.

The discovery of 3-[(5-Chloro-2-nitrophenyl)phenylamino]-3-oxopropanoic acid ethyl ester can be traced back to the exploration of compounds designed to interact with specific biological targets, particularly in the context of anti-inflammatory and analgesic activities. Researchers focused on modifying existing frameworks to improve efficacy and selectivity towards certain pathways involved in disease processes. The incorporation of a 5-chloro-2-nitrophenyl group in the structure enhances the compound's pharmacological profile, potentially increasing its effectiveness as a therapeutic agent.

In terms of application, this compound has been investigated for its anti-inflammatory properties, making it a candidate for treating conditions such as arthritis and other inflammatory diseases. The presence of the nitrophenyl group is thought to contribute to its mechanism of action, possibly through the modulation of signaling pathways associated with inflammation. The ethyl ester functionality may enhance the compound's bioavailability, allowing for better absorption and efficacy in biological systems.

Research into this compound is ongoing, with studies focusing on its pharmacokinetics, toxicity, and overall therapeutic potential. Investigators are examining the compound's interactions with specific receptors and enzymes that play pivotal roles in inflammatory processes. The aim is to elucidate the molecular mechanisms by which this compound exerts its effects, paving the way for the development of novel anti-inflammatory therapies based on its structure.

In addition to its potential therapeutic uses, 3-[(5-Chloro-2-nitrophenyl)phenylamino]-3-oxopropanoic acid ethyl ester may also serve as a valuable tool in chemical biology. Its unique structural characteristics can facilitate the exploration of biochemical pathways and the development of targeted therapies. Overall, the compound represents an intriguing addition to the library of chemical entities being investigated for their pharmacological potential.

References

2003. Clobazam. *Pharmaceutical Substances*.
URL: KD-03-0192