4-[2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide
[CAS# 33456-68-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Isoquinoline compound
• Name: 4-[2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide
• Synonyms: 4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]benzenesulfonamide
• Molecular Formula: C₂₀H₂₂N₂O₅S
• Molecular Weight: 402.46
• CAS Registry Number: 33456-68-7
• EC Number: 251-529-0
• SMILES: CC1(C2=C(C=C(C=C2)OC)C(=O)N(C1=O)CCC3=CC=C(C=C3)S(=O)(=O)N)C

Properties

• Density: 1.298±0.1 g/cm³, Calc.^*
• Melting point: 200-202 °C (Expl.)
• Index of Refraction: 1.591, Calc.^*
• Boiling Point: 643.7±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 343.1±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-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

4-[2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide is a synthetic compound with a complex structure, incorporating an isoquinoline derivative, a sulfonamide group, and a substituted benzene ring. The discovery of this molecule is rooted in efforts to design small molecules with potential therapeutic applications, particularly within the realm of oncology and anti-inflammatory research. This compound belongs to a class of molecules often investigated for their ability to modulate biological pathways, making it an important tool for studying disease mechanisms and therapeutic interventions.

Chemically, the molecule features a 1,3-dioxoisoquinoline core, known for its bioactivity and stability, functionalized with a methoxy group and two methyl groups, which contribute to its lipophilicity. The ethyl linkage to a benzenesulfonamide adds further versatility, as sulfonamide groups are well-recognized pharmacophores in medicinal chemistry. The combination of these structural elements makes the compound a candidate for targeting enzymes and proteins involved in cell signaling and proliferation.

Applications of 4-[2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide span multiple research domains. One of its primary uses is as an experimental agent in the development of inhibitors targeting kinases or other enzymes associated with cancer growth. Isoquinoline derivatives have shown promise in modulating signaling pathways like MAPK or PI3K, crucial in tumorigenesis. The incorporation of a sulfonamide group enhances the compound's ability to bind to enzyme active sites, increasing its specificity and potency.

Another area of interest is its potential use as an anti-inflammatory agent. The sulfonamide moiety has been linked to activity against pro-inflammatory mediators, and studies have explored similar compounds for their ability to inhibit cytokine production or block inflammatory pathways. This has led to preliminary evaluations of the compound in models of autoimmune diseases and chronic inflammation, although more research is needed to fully elucidate its mechanism of action.

In addition to therapeutic research, this compound is utilized as a chemical probe to study protein-ligand interactions. Its well-defined structure and pharmacophoric elements make it a useful tool for crystallographic studies, helping researchers understand the binding dynamics of structurally similar inhibitors. This information is crucial for optimizing drug design, ensuring better efficacy and safety profiles for related compounds.

Future developments involving 4-[2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide may include its application in drug delivery systems. The compound’s physicochemical properties suggest potential for further derivatization, enabling it to serve as a carrier or targeting moiety in advanced therapeutic platforms. Furthermore, ongoing studies are exploring its interactions with biomolecules to expand its utility across other therapeutic areas.

Overall, the synthesis and application of this molecule reflect the broader efforts in medicinal chemistry to design multi-functional compounds that address complex biological challenges, demonstrating the role of structure-based design in advancing therapeutic innovations.

References

2003. Gliquidone. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-07-0030