N-(2-(2-Methoxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide
[CAS# 149456-98-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: N-(2-(2-Methoxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide
• Synonyms: N-[2-[4-(methanesulfonamido)-2-methoxy-5-phenoxyphenyl]-2-oxoethyl]formamide
• Molecular Formula: C₁₇H₁₈N₂O₆S
• Molecular Weight: 378.40
• CAS Registry Number: 149456-98-4
• SMILES: COC1=CC(=C(C=C1C(=O)CNC=O)OC2=CC=CC=C2)NS(=O)(=O)C

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.595, Calc.^*
• Boiling Point: 619.1±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 328.2±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P351-P302+P352

Discovery and Applications

N-(2-(2-Methoxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide is a complex organic compound with functional groups including a methoxy group, a sulfonamide moiety, a phenoxy substituent, and a formamide group. This intricate molecular architecture provides the compound with unique chemical properties and potential applications in medicinal and materials chemistry.

The discovery of this compound lies at the intersection of sulfonamide chemistry and the development of bioactive molecules. Sulfonamides, first introduced in the early 20th century as antimicrobial agents, have since been expanded to a broader range of therapeutic applications, including anti-inflammatory, anticancer, and antidiabetic drugs. The incorporation of additional functional groups, such as the formamide moiety in this compound, further diversifies its potential activity profile and interactions with biological targets.

This compound has been investigated for its therapeutic potential, particularly in modulating enzymatic pathways associated with inflammation and oxidative stress. The methylsulfonamide group is a key feature, as it can form strong hydrogen bonds with protein active sites, enhancing binding affinity and specificity. Meanwhile, the methoxy and phenoxy substituents provide hydrophobic interactions and influence the electronic properties of the molecule, contributing to its overall bioactivity.

In the realm of pharmacology, N-(2-(2-methoxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide has been explored for its anti-inflammatory and anticancer properties. It has demonstrated potential in inhibiting pro-inflammatory enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), which are implicated in inflammatory diseases. Furthermore, preliminary in vitro studies suggest that the compound may exhibit selective cytotoxicity against certain cancer cell lines, making it a promising candidate for further investigation in oncology.

From a materials science perspective, the compound's ability to form stable hydrogen bonds and interact with various substrates opens possibilities for its use in designing advanced functional materials. The sulfonamide and formamide groups, in particular, contribute to its chemical stability and reactivity, which could be harnessed in polymer chemistry or surface modification technologies.

Despite its promise, challenges remain in advancing this compound toward practical applications. Comprehensive studies on its pharmacokinetics, toxicity, and environmental impact are needed to establish its suitability for therapeutic or industrial use. Additionally, synthetic methods for producing the compound must be optimized to ensure scalability and cost-efficiency.

The synthesis and exploration of N-(2-(2-methoxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide underscore the importance of rational drug design and multifunctional molecule development. Its diverse functional groups and potential biological activities exemplify the innovative approaches in modern chemistry aimed at addressing complex challenges in health and technology.

References

2007. Determination of iguratimod in rat plasma by high performance liquid chromatography: method and application. Biomedical chromatography : BMC, 22, 1.
DOI: 10.1002/bmc.921