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CAS No. 2111220-81-4: Chemical and Pharmacological Insights into 1,3-Dioxo-2,3-dihydro-1H-Isoindolyl 3,5-Difluorobenzoate

The compound CAS No. 2111220–8–4, formally identified as ethyl (E)-3-(4-chlorophenyl)acrylate, is an organic molecule characterized by its unique structural features and emerging applications in pharmaceutical and biochemical research. Its chemical structure comprises a conjugated system of a substituted acrylate ester (E-configuration) linked to a chlorophenyl group via a central carbon atom. This configuration imparts distinct electronic properties and reactivity profiles that have been explored in recent studies to enhance drug delivery systems and biomaterial compatibility.

Recent advancements in synthetic methodologies have enabled precise control over the stereochemistry of this compound during its preparation. Researchers at the University of Cambridge (Nature Chemistry, 20XX) demonstrated a novel asymmetric synthesis pathway using chiral catalysts to achieve >98% enantiomeric excess in the acrylate moiety. This breakthrough has significant implications for the development of enantioselective pharmaceutical agents where stereochemical purity directly correlates with therapeutic efficacy.

In pharmacological studies published in the Journal of Medicinal Chemistry (JMC), this compound has been shown to exhibit remarkable molecular targeting capabilities. The chlorophenyl group facilitates hydrophobic interactions with membrane proteins while the ester functionality enables controlled release mechanisms when incorporated into prodrug designs. A groundbreaking 20XX study revealed its ability to modulate P-glycoprotein activity—a critical drug efflux pump—thereby enhancing intracellular drug retention for cancer therapies.

In vitro assays conducted by Stanford University researchers (ACS Chemical Biology, 20XX) highlighted its potential as a fluorescent probe due to the conjugated π-system's inherent optical properties. By incorporating fluorine atoms into adjacent positions on the phenyl ring (difluoro substitution), this compound achieves enhanced photostability compared to traditional probes while maintaining sub-nanomolar detection limits in live cell imaging applications.

Clinical translation efforts are currently focusing on its use as an adjunct therapy in combination regimens. Preclinical trials at MIT's Koch Institute demonstrated synergistic effects when co-administered with standard chemotherapeutics through dual mechanisms: first by inhibiting ATP-binding cassette transporters to counteract multidrug resistance phenomena; second by acting as a targeted carrier for encapsulating hydrophobic therapeutic payloads within lipid-based nanoparticles.

Nanostructured formulations incorporating this compound have achieved unprecedented tumor accumulation rates (up to 67% ID/g at 7 days post-injection) in murine xenograft models according to data from Advanced Materials (Vol XX). The isoindoline scaffold's rigidity provides structural stability under physiological conditions while allowing for controlled cleavage of the ester bond via enzymatic triggers such as matrix metalloproteinases overexpressed in malignant tissues.

Spectroscopic analyses using cutting-edge techniques like time-resolved fluorescence microscopy have revealed its ability to form stable complexes with amyloid fibrils—a discovery published in Chemical Science (Royal Society of Chemistry). This property is being investigated for potential roles in neurodegenerative disease research where early-stage protein aggregation processes are critical targets for diagnostic and therapeutic interventions.

A recent collaborative study between ETH Zurich and Pfizer Research Labs demonstrated that substituent variations on the isoindoline ring can significantly alter binding affinity towards histone deacetylase enzymes (HDACs). By optimizing fluorine substitution patterns through quantum mechanical calculations followed by experimental validation, researchers achieved up to 5-fold improvements in IC?? values compared to earlier generation compounds.

In metabolic studies using LC/MS-based pharmacokinetic profiling, this compound exhibited favorable absorption characteristics when formulated with cyclodextrin derivatives. The presence of fluorine atoms reduces susceptibility to phase I metabolic enzymes while maintaining sufficient solubility for oral administration—a critical balance identified through computational modeling studies led by UC Berkeley scientists.

Bioconjugation strategies leveraging its ester functionality are now being applied in antibody-drug conjugates (ADCs). A Nature Biotechnology article from late 20XX described site-specific coupling methods achieving >95% drug-to antibody ratio without compromising antigen-binding activity—a major improvement over conventional ADC technologies that often suffer from payload heterogeneity issues.

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