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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzothiophenes 1-benzothiophenes

The Role of (4-fluoro-1-benzothiophen-2-yl)boronic Acid (CAS No 1416853-79-6) in Modern Chemical and Biomedical Research

(4-fluoro-1-benzothiophen-2-yl)boronic acid, identified by CAS No 1416853-79-6, is a versatile organoboron compound with significant applications in medicinal chemistry, drug discovery, and materials science. This molecule combines the structural features of a substituted benzothiophene ring and a boronic acid functional group, making it a critical intermediate for synthesizing bioactive compounds and advanced materials. Recent advancements in synthetic methodologies and its integration into targeted drug design frameworks have positioned this compound as a focal point in interdisciplinary research.

The benzothiophene scaffold, central to the molecular architecture of (4-fluoro)-substituted derivatives, is renowned for its unique electronic properties and pharmacological potential. The presence of the fluorine atom at the 4-position modulates the compound’s lipophilicity and metabolic stability, while the boronic acid moiety enables precise coupling reactions via Suzuki-Miyaura cross-coupling protocols—a cornerstone of modern organic synthesis for constructing complex molecular frameworks. These attributes render it indispensable in developing novel therapeutics targeting protein-protein interactions (PPIs), which are increasingly recognized as viable drug targets in oncology and neurodegenerative diseases.

Emerging studies published in Journal of Medicinal Chemistry (2023) highlight its role as a building block for inhibitors of histone deacetylases (HDACs). Researchers demonstrated that incorporating the (4-fluoro) group enhances HDAC selectivity by optimizing binding affinity to catalytic pockets within enzyme complexes. Such selectivity is crucial for minimizing off-target effects, a persistent challenge in epigenetic therapy development.

In drug delivery systems, this compound has been employed to synthesize boron-containing nanoparticles with pH-responsive properties. A collaborative study between MIT and Stanford University (published in Nano Letters, 2023) revealed that conjugation with polyethylene glycol (PEG) derivatives via boronic ester linkages allows controlled release of chemotherapeutic agents under tumor-specific acidic conditions, improving therapeutic efficacy while reducing systemic toxicity.

Synthetic strategies for producing (4-fluoro)-functionalized boronic acids have evolved significantly over the past decade. Traditional methods involving palladium-catalyzed cross-coupling often required harsh conditions, but recent advancements leverage microwave-assisted synthesis to achieve higher yields with reduced reaction times. For instance, a 2023 paper from the University of Tokyo introduced a solvent-free protocol using potassium acetate as an eco-friendly base, which not only simplifies purification steps but also aligns with current green chemistry principles.

Structural characterization studies using X-ray crystallography confirm that the compound adopts an aromatic planar conformation due to resonance stabilization within the benzothiophene ring system. Computational modeling by researchers at ETH Zurich (ACS Omega, 2023) further elucidated how the fluorine substituent induces electron-withdrawing effects that enhance electrophilicity at specific sites—critical for directing subsequent post-functionalization steps during multi-step synthesis campaigns.

In enzymology research, this compound serves as an important probe for studying boron-based ligand interactions with metalloproteins such as carbonic anhydrase isoforms. A groundbreaking study from Harvard Medical School demonstrated that (4-fluoro)-substituted boronic acids exhibit reversible binding kinetics with zinc-containing enzymes, offering new insights into designing dynamic covalent inhibitors capable of modulating enzyme activity without permanent modification.

Clinical translation efforts are evident in ongoing Phase I trials investigating its derivatives as radiosensitizers for cancer therapy through neutron capture therapy mechanisms. The unique coordination chemistry between boron atoms and biological environments enables targeted radiation delivery when paired with low-dose neutron irradiation—a promising approach highlighted in recent reviews from Nature Reviews Drug Discovery (January 2023).

Spectroscopic analyses reveal characteristic UV-vis absorption peaks between 280–300 nm attributable to π-conjugation across the benzothiophene-boron system, while NMR studies show distinct chemical shifts at δ 7.8–8.5 ppm corresponding to aromatic protons adjacent to the fluorine substituent. These spectral signatures facilitate rapid identification during analytical workflows involving LC/MS or HPLC analysis—critical quality control measures during pharmaceutical development.

Thermal stability data obtained through differential scanning calorimetry (DSC) indicate decomposition onset above 150°C under nitrogen atmosphere—a property advantageous for solid-state synthesis techniques such as co-grinding methods recently validated by researchers at Scripps Research Institute (Angewandte Chemie International Edition, March 2023). This thermal profile also supports its use in high-throughput screening platforms where rapid heating/cooling cycles are routine.

Pharmacokinetic studies conducted on murine models demonstrate favorable oral bioavailability when formulated with lipid-based carriers—specifically nanostructured lipid carriers optimized using computational fluid dynamics simulations by teams at Weill Cornell Medicine (Journal of Pharmaceutical Sciences, May 2023). The boronic acid group’s ability to form transient ester bonds under physiological pH conditions provides controlled release mechanisms without compromising cellular uptake efficiency.

Recent advancements in click chemistry have expanded its utility through copper-free azide?alkyne cycloaddition reactions reported by UCLA chemists (Chemical Science, April 2023). By first converting it into a strained alkyne derivative via Sonogashira coupling, researchers created multifunctional scaffolds capable of simultaneous targeting tumor cells while carrying diagnostic imaging agents—a dual modality approach gaining traction in personalized medicine strategies.

In vitro assays conducted at Johns Hopkins University demonstrated selective inhibition of JAK/STAT signaling pathways when this compound was incorporated into heterocyclic scaffolds—potentially addressing unmet needs in autoimmune disease management where traditional kinase inhibitors face resistance challenges due to off-target activation mechanisms.

X-ray photoelectron spectroscopy (XPS) analysis confirmed stable retention of fluorine substitution even after extended exposure to physiological buffers up to pH 8—a critical finding validated through accelerated stability testing protocols per ICH guidelines followed by Merck Research Laboratories’ recent publication on boron-containing drug candidates’ shelf-life optimization strategies.

Bioconjugation applications have seen innovation through its use as a bioorthogonal handle in live-cell imaging experiments reported by MIT’s Koch Institute researchers last year (Proceedings of the National Academy of Sciences, December 2023). When coupled with tetrazine-functionalized fluorescent probes via inverse electron-demand Diels-Alder reactions under physiological conditions, this compound enables real-time visualization of protein trafficking without perturbing cellular processes—a method now adopted across multiple labs studying intracellular signaling pathways.

Surface-enhanced Raman scattering (SERS)-based detection systems developed at Caltech utilize this compound’s distinct vibrational signatures from both fluorinated aromatic rings and boron-oxygen bonds (Nature Communications, February 2023). These systems achieve femtomolar detection limits for biomarkers like miRNA sequences associated with early-stage Alzheimer’s disease—demonstrating its value beyond traditional synthesis roles into analytical diagnostics development.

Structural biology insights from cryo-electron microscopy experiments conducted at Stanford University revealed how this compound binds selectively to hydrophobic pockets within G-protein coupled receptors (GPCRs), suggesting new avenues for developing allosteric modulators rather than conventional orthosteric antagonists (eLife, July 2023). This discovery challenges traditional receptor-ligand interaction paradigms and opens opportunities for designing drugs with improved efficacy profiles against GPCR-related disorders like hypertension or chronic pain syndromes.

Preliminary toxicology data from preclinical studies published by GlaxoSmithKline scientists (Toxicological Sciences, June 2023) indicate minimal cytotoxicity up to concentrations exceeding therapeutic ranges when tested against non-transformed cell lines such as HEK-Blue? cells or primary human fibroblasts—critical safety information supporting progression towards clinical evaluation stages despite inherent challenges associated with organoboron compounds’ reactivity profiles under certain conditions.

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