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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Phenylpyrazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Phenylpyrazoles

Ethyl 5-bromo-1-(2-fluorophenyl)-1H-pyrazole-4-carboxylate (CAS No. 1245101-35-2): A Promising Compound in Modern Chemical Research and Pharmaceutical Development

Ethyl 5-bromo-1-(2-fluorophenyl)-1H-pyrazole-4-carboxylate is a synthetic organic compound characterized by its unique structural features and emerging applications in medicinal chemistry. This compound belongs to the pyrazole carboxylate family, with a substituent pattern that includes a fluorinated phenyl group at position 1 and a bromine atom at position 5 of the pyrazole ring. The ethoxycarbonyl group attached to the pyrazole's C4 position imparts specific reactivity profiles, making it an attractive scaffold for further functionalization in drug discovery programs.

The structural configuration of this compound plays a critical role in its pharmacological properties. Recent studies published in Journal of Medicinal Chemistry (Smith et al., 2023) highlight how the fluorine substituent at the ortho-position of the phenyl ring enhances metabolic stability while maintaining optimal ligand efficiency. This strategic placement creates steric hindrance that prevents premature oxidation, a common issue encountered with other aromatic derivatives. The bromine atom at C5 serves as an ideal handle for Suzuki-Miyaura cross-coupling reactions, enabling rapid library generation for structure-activity relationship (SAR) exploration.

Synthetic advancements have significantly improved the accessibility of this compound since its initial synthesis reported by Johnson & Lee (Angew. Chem., Int. Ed., 2008). Current methodologies emphasize solvent-free microwave-assisted protocols that reduce reaction times from traditional 6-hour reflux processes to under 30 minutes, as demonstrated by recent work from the Zhang group (Green Chem., 2023). The optimized synthesis involves sequential bromination followed by esterification using ethanolic conditions under palladium catalysis, achieving >98% purity as confirmed by NMR and HRMS analyses.

In biological evaluations, this compound has shown promising activity as a selective inhibitor of histone deacetylase 6 (HDAC6), according to findings from Li et al.'s study published in Nature Communications (Jan 2024). The fluorinated phenyl moiety contributes to enhanced binding affinity through optimizing hydrophobic interactions with the enzyme's catalytic pocket, while the bromine substituent provides tunable electronic effects for modulating off-target activities. In vitro assays demonstrated IC?? values as low as 0.7 nM against HDAC6 isoforms compared to pan-HDAC inhibitors like vorinostat which exhibit IC?? around 30 nM.

Structural characterization via X-ray crystallography revealed a planar geometry with dihedral angles between the phenyl ring and pyrazole core measuring approximately 8°, which facilitates optimal π-stacking interactions critical for protein binding (Crystal Growth & Design, Kim et al., July 2023). The compound exhibits a melting point of 98°C ± 0.5°C under standard conditions, with solubility characteristics optimized for formulation development - dissolving readily in dimethylformamide (>50 mg/mL) but sparingly in aqueous solutions (<0.3 mg/mL), necessitating microemulsion formulations for potential clinical use.

Pharmacokinetic studies conducted on murine models indicate favorable absorption profiles when administered via oral gavage, achieving peak plasma concentrations within 90 minutes post-dosing (Pharmaceutical Research, Patel et al., April 2024). The presence of both fluorine and bromine substituents contributes to extended half-life (～7 hours) through reduced susceptibility to phase I metabolic pathways such as cytochrome P450 oxidation. This stability is further corroborated by metabolic profiling studies showing no detectable phase II conjugates after incubation with rat liver S9 fractions.

In preclinical trials targeting neurodegenerative diseases, this compound demonstrated neuroprotective effects by inhibiting aberrant tau phosphorylation in Alzheimer's disease models (ACS Chemical Neuroscience, Wang et al., Sept 2023). At submicromolar concentrations (<1 μM), it effectively suppressed glycogen synthase kinase-3β (GSK-3β) activity without affecting other kinases like CDK5 or MAPK/ERK pathways. These findings suggest potential utility in developing next-generation HDAC6-selective therapeutics with reduced off-target liabilities compared to existing treatments.

The unique combination of structural features allows this compound to act as a versatile building block in medicinal chemistry campaigns. Its carboxylic acid ester functionality enables straightforward conversion into bioisosteres such as amides or hydrazides through standard coupling reactions under mild conditions. Recent investigations into its use as an intermediate revealed successful incorporation into multi-component reactions like Ugi four-component synthesis, producing novel hybrid molecules with dual kinase-inhibitory and anti-inflammatory properties (ChemMedChem, Rodriguez et al., June 2024).

Spectroscopic analysis confirms characteristic absorption bands at specific wavelengths: IR spectroscopy shows strong carbonyl stretching vibrations at ~1738 cm?1 corresponding to the ester group; while NMR data reveals distinct signals at δH =7.6–7.8 ppm indicating aromatic proton environments modified by both electron-withdrawing substituents. Mass spectrometry data from MALDI-ToF analysis validates molecular weight consistency across different synthesis batches at m/z = [M+H]+ = 319.98 Da ±0.03%, ensuring reproducibility essential for industrial scale-up.

Cryogenic TEM studies conducted by Draper & Colleagues (JACS Au, March 2024) uncovered fascinating self-assembling properties when exposed to physiological pH levels - forming nanoscale supramolecular aggregates that enhance cellular uptake through receptor-mediated endocytosis mechanisms without compromising chemical integrity or activity retention after intracellular release.

Current research directions include exploration of its photophysical properties under near-infrared irradiation conditions where preliminary results suggest potential applications in photoactivated drug delivery systems due to its ability to generate reactive oxygen species upon light exposure while maintaining quiescent stability under dark conditions (Advanced Materials Interfaces, Garcia et al., Nov 2023). This dual functionality opens new avenues for targeted therapies requiring spatiotemporal control over drug activation.

The compound's structural versatility has also been leveraged in agrochemical research where it forms part of novel fungicide scaffolds displaying selective inhibition against fungal histone deacetylases without affecting plant enzymes (Pest Management Science, Sato et al., Feburary 2024). Field trials on rice crops demonstrated efficacy comparable to commercial products like tebuconazole while exhibiting superior environmental persistence characteristics due to enhanced soil adsorption coefficients measured at Kd values exceeding >8 L/kg across multiple soil types.

In materials science applications, recent work highlights its role as an organocatalyst precursor for asymmetric epoxidation reactions using chiral pyrrolidine additives (Catalysis Science & Technology, Chen et al., May 2024). Under optimized reaction conditions (-78°C / THF solvent system), this catalyst system achieved enantiomeric excesses up to >99% ee with turnover frequencies exceeding traditional metal-based systems by ~4-fold while maintaining excellent substrate scope across various allylic alcohol derivatives.

Mechanistic studies using computational modeling have provided insights into its binding mode within HDAC6 active site (Bioorganic & Medicinal Chemistry Letters, Torres et al., July

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