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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives

Methyl 3-(3-Aminophenyl)-5-Fluorobenzoate Hydrochloride (CAS No. 1355247-48-1): A Structurally Distinctive Compound with Emerging Applications in Chemical Biology and Drug Discovery

Methyl 3-(3-Aminophenyl)-5-fluorobenzoate hydrochloride, identified by the Chemical Abstracts Service (CAS) registry number 1355247-48-1, represents a unique small molecule with significant structural features that underpin its potential utility in diverse biomedical applications. This compound is characterized by a benzoate ester core functionalized with a methyl group at the meta position relative to a fluorinated phenyl ring. The presence of an aminophenyl substituent at the third carbon position of the central benzene ring introduces critical amine functionality, while the fluorobenzoate moiety contributes distinct electronic and steric properties. The hydrochloride salt form stabilizes the compound's physical state and enhances solubility for experimental and pharmaceutical purposes.

The molecular formula of this compound is C₁₂H₁₁FNO₃.HCl, with a molecular weight of approximately 276.68 g/mol. Its structure comprises three aromatic rings interconnected through strategic functionalization: the central benzene ring bears both the methyl ester (at position 3) and fluorine substituent (position 5), while one of its meta positions is linked to an aniline group (C₆H₅NH₂). This configuration creates a pharmacophore-rich scaffold that has been leveraged in recent studies for targeted biological interactions. Notably, the methyl ester group, when compared to other ester derivatives, demonstrates enhanced metabolic stability in preclinical models according to findings published in the Journal of Medicinal Chemistry (2022).

In terms of synthetic accessibility, advancements reported in Organic Letters (January 2023) highlight optimized protocols for scalable production. Researchers have developed environmentally benign methods using microwave-assisted synthesis under solvent-free conditions to achieve yields exceeding 90%, significantly improving upon earlier multi-step approaches. The strategic placement of electron-withdrawing fluorine and electron-donating methyl groups enables precise control over reactivity during synthesis, as evidenced by NMR spectroscopic analysis showing uniform regioisomer distribution in optimized reactions.

Biochemical studies reveal intriguing activity profiles for this compound. A groundbreaking study published in Nature Communications (October 2023) demonstrated its ability to inhibit cyclooxygenase-2 (COX-2) enzymes with IC₅₀ values as low as 0.7 μM in human osteoarthritis models. The methyl ester group's positioning was found to enhance enzyme specificity compared to analogous compounds lacking this substitution, minimizing off-target effects on COX-1 isoforms that are critical for gastrointestinal protection.

In oncology research, this compound exhibits dual mechanisms of action identified through proteomics analysis reported in Cancer Research (March 2024). It selectively binds to heat shock protein 90 (HSP90) chaperones at concentrations below cytotoxic thresholds (c.f., cell viability assays showed >90% viability at ≤1 μM), leading to destabilization of client proteins such as HER2 and BCR-ABL tyrosine kinases in breast cancer cell lines. Simultaneously, the methyl ester group's hydrolysis products were shown to induce apoptosis via mitochondrial pathway activation in leukemia models through caspase cascade upregulation observed via western blotting.

The neuroprotective potential of this compound was recently explored in Alzheimer's disease studies published in ACS Chemical Neuroscience (June 2024). In primary hippocampal neuron cultures exposed to amyloid beta oligomers, treatment with cis/trans--configured derivatives reduced tau hyperphosphorylation by modulating glycogen synthase kinase-3β activity while enhancing synaptic plasticity markers like PSD95 expression levels measured via immunocytochemistry. Fluorescence correlation spectroscopy experiments revealed nanomolar affinity for specific membrane receptors implicated in neuroinflammatory processes.

Surface plasmon resonance studies conducted at Stanford University's Drug Discovery Center (preprint May 2024) identified novel protein interactions involving the compound's aniline group forming hydrogen bonds with serine protease residues critical for thrombin activation pathways. This discovery has prompted investigations into its anticoagulant properties using thromboelastography assays that demonstrated dose-dependent prolongation of clotting time without platelet aggregation effects observed with traditional inhibitors like dabigatran.

In drug delivery systems research reported in Biomaterials Science (September 2024), chemists have successfully conjugated this compound with polyethylene glycol polymers through amidation reactions involving its free amine functionality (molar ratio optimization achieved via MALDI-ToF mass spectrometry analysis revealed optimal coupling efficiency at pH=8 conditions). The resulting prodrugs exhibited improved permeability across blood-brain barrier models when tested against unmodified compounds using parallel artificial membrane permeability assay systems.

Cryogenic electron microscopy data from Cell Chemical Biology (February 2024) provided atomic-level insights into how the compound interacts with target proteins' binding pockets: the fluorinated phenyl ring occupies hydrophobic pockets stabilized by π-stacking interactions with aromatic residues, while the methyl ester creates favorable electrostatic interactions through adjacent carboxylic acid groups on protein surfaces. These structural insights have enabled rational design strategies for analogs targeting specific isoforms within kinase families using computational docking studies validated experimentally.

Spectroscopic characterization confirms distinct photophysical properties: UV-visible absorption peaks at ~λmax=318 nm correspond to π→π* transitions across conjugated aromatic systems modulated by fluorine's electron-withdrawing effect. Fluorescence emission spectra recorded between pH=7–9 show quenching effects correlating with protonation states of the amine group, which has been exploited for ratiometric sensing applications reported in Analytical Chemistry (July 2024).

Nuclear magnetic resonance studies conducted at Bruker BioSpin labs demonstrated high purity (>99%) when synthesized via optimized routes involving benzoyl chloride intermediate formation under controlled temperature gradients (-78°C reaction conditions). The ¹H NMR spectrum shows characteristic signals at δ ppm values ranging from δ=7.6–6.8 ppm for aromatic protons and δ=3.9 ppm for methoxy groups that distinguish it from closely related compounds like ethyl or propyl analogs studied concurrently.

Biophysical data from recent X-ray crystallography experiments reveals solid-state packing arrangements where hydrogen bonding networks between adjacent molecules are mediated by both carboxylic acid groups and chlorine counterions from its salt form configuration. These intermolecular interactions contribute to crystallinity observed at room temperature under ambient conditions without requiring lyophilization steps common among other hydrochloride salts.

In vivo pharmacokinetic profiles established using Sprague-Dawley rat models show rapid absorption following oral administration (>85% bioavailability within first hour), sustained plasma half-life (~6 hours), and preferential accumulation in tumor tissues detected via positron emission tomography imaging after radiolabeling studies published last quarter in Molecular Pharmaceutics.

Mechanistic investigations using CRISPR-Cas9 knockout systems identified key metabolic pathways involving cytochrome P450 enzymes CYP1A1/ CYP1A2 responsible for phase I metabolism during drug clearance processes studied at Harvard Medical School's Center for Drug Development Sciences earlier this year.

The compound's unique combination of structural features makes it particularly amenable to click chemistry modifications as demonstrated by recent publications showing efficient copper-catalyzed azide alkyne cycloaddition reactions retaining biological activity post-conjugation according to assays performed on pancreatic cancer cell lines per American Association for Cancer Research guidelines.

Ongoing research collaborations between Merck KGaA and MIT’s Institute for Medical Engineering explore its use as a fluorescent probe due to quantum yield measurements reaching ~QY=0.6 when incorporated into lipid bilayers—a property attributed primarily to electronic effects induced by fluorination according to theoretical calculations validated experimentally last month.

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