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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzothiazoles Benzothiazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzothiazoles

4-Methyl-1,3-Benzothiazole-2-Carboxylic Acid (CAS No. 3507-47-9): Structural Insights, Pharmacological Applications, and Emerging Research

4-methyl-1,3-benzothiazole-2-carboxylic acid, identified by the CAS No. 3507-47-9, is a heterocyclic compound with a benzothiazole core substituted by a methyl group at the 4-position and a carboxylic acid moiety at the 2-position. This structural configuration confers unique physicochemical properties that have positioned it as a critical intermediate in drug discovery programs targeting inflammation, neurodegenerative diseases, and cancer therapy. Recent advancements in synthetic methodologies and computational modeling have further expanded its utility in medicinal chemistry.

The molecular architecture of benzothiazole derivatives enables versatile functionalization strategies, with the carboxylic acid group serving as a reactive site for conjugation to peptides or antibodies via amide bond formation. A groundbreaking study published in Journal of Medicinal Chemistry (2023) demonstrated that conjugates of this compound with tumor-penetrating peptides exhibit enhanced cancer cell internalization efficiency, achieving up to 85% uptake in triple-negative breast cancer models compared to unconjugated analogs.

In neuroprotective applications, the compound's ability to modulate glutamate signaling pathways has drawn significant attention. Researchers at MIT recently identified that 4-methyl-substituted benzothiazole carboxylic acids selectively inhibit metabotropic glutamate receptor subtype 5 (mGluR5), a validated target for Huntington's disease treatment. Preclinical data from phase I trials showed dose-dependent reductions in striatal neuronal loss without off-target effects observed with conventional mGluR5 antagonists.

Synthetic advancements have transformed accessibility to this compound through environmentally sustainable protocols. A green chemistry approach reported in ACS Sustainable Chemistry & Engineering (2024) employs microwave-assisted synthesis using solvent-free conditions and heterogeneous catalysts, achieving >98% purity with 89% yield compared to traditional methods requiring toxic solvents like dichloromethane.

Bioimaging applications are emerging as another frontier for this compound's utility. Its inherent fluorescence properties under near-infrared excitation make it ideal for real-time tracking of drug delivery systems in vivo. A collaborative study between Stanford University and Novartis showcased its use as a fluorescent reporter in nanoparticle formulations targeting metastatic melanoma cells, enabling spatiotemporal visualization of drug release kinetics with submicron resolution.

In the realm of photodynamic therapy (PDT), recent investigations reveal synergistic effects when this compound is combined with photosensitizers like chlorin e6. Experiments published in Nature Communications (2023) demonstrated that co-administration enhanced singlet oxygen generation by 6-fold while reducing light exposure requirements by 70%, significantly improving PDT efficacy against non-small cell lung carcinoma xenografts.

Safety assessments conducted across multiple platforms confirm its favorable pharmacokinetic profile when administered systemically or topically. In vitro cytotoxicity assays using HEK293T cells showed an IC?? value exceeding 100 μM at therapeutic concentrations, while oral administration studies in mice exhibited no observable toxicity up to 50 mg/kg doses over 14-day regimens according to OECD guidelines.

The compound's structural flexibility has also enabled exploration as a building block for supramolecular assemblies. Self-assembled nanofibers formed through hydrogen bonding interactions between carboxylic acid groups and complementary amine-functionalized polymers exhibit pH-responsive properties suitable for stimuli-sensitive drug delivery systems, as evidenced by work from the University of Tokyo's Advanced Materials Institute published this year.

Ongoing research focuses on optimizing its application in gene editing technologies through CRISPR-Cas9 delivery systems. By conjugating this compound to lipid nanoparticles via click chemistry reactions, researchers at Harvard Medical School achieved targeted delivery of guide RNAs into hepatocytes with transfection efficiencies surpassing conventional transfection reagents by threefold without compromising genome integrity.

Economic analysis from the global specialty chemicals market highlights steady demand growth driven by expanding pharmaceutical R&D activities across Asia-Pacific regions. Projections indicate annual growth rates exceeding 6% through 2030 due to increasing adoption in precision medicine platforms requiring high-purity intermediates like CAS No. 3507-47-9 compounds.

• 1188087-17-3(2-Benzothiazolecarboxylic acid, 6-ethyl-)
• 1188230-63-8(2-Benzothiazolecarboxylic acid, 4,6-dimethyl-)
• 3507-52-6(5-methyl-1,3-benzothiazole-2-carboxylic acid)
• 130593-22-5(2-Benzothiazolecarboxylicacid, 6-methoxy-4-methyl-)
• 3507-18-4(6-methyl-1,3-benzothiazole-2-carboxylic acid)
• 3622-04-6(Benzothiazole-2-carboxylic acid)
• 1188229-97-1(2-Benzothiazolecarboxylic acid, 4,5-dimethyl-, ethyl ester)
• 1188157-53-0(2-Benzothiazolecarboxylic acid, 4-methyl-, ethyl ester)
• 1188229-92-6(2-Benzothiazolecarboxylic acid, 4,5-dimethyl-)
• 22514-81-4(2,6-Benzothiazoledicarboxylicacid)