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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoquinolines and derivatives Isoquinolines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoquinolines and derivatives

Methyl 4-Hydroxyisoquinoline-3-Carboxylate (CAS No. 1108146-90-2): A Comprehensive Overview

Methyl 4-hydroxyisoquinoline-3-carboxylate (CAS No. 1108146-90-2) is a versatile organic compound that has garnered significant attention in recent years due to its unique chemical structure and potential applications in various fields, including pharmaceuticals, materials science, and chemical synthesis. This compound is characterized by its isoquinoline core, which is a common scaffold in many biologically active molecules. The presence of a hydroxyl group and a carboxylate ester moiety further enhances its reactivity and functional versatility.

The chemical formula of methyl 4-hydroxyisoquinoline-3-carboxylate is C₁₂H₁₁NO₄, and its molecular weight is approximately 233.22 g/mol. The compound can be synthesized through various methods, including the condensation of 4-hydroxyisoquinoline-3-carbaldehyde with methanol in the presence of an acid catalyst. This synthetic route has been optimized to achieve high yields and purity, making it suitable for large-scale production.

In the realm of pharmaceutical research, methyl 4-hydroxyisoquinoline-3-carboxylate has shown promising potential as a lead compound for the development of novel therapeutic agents. Recent studies have demonstrated its ability to modulate various biological pathways, including those involved in inflammation, oxidative stress, and cell signaling. For instance, a study published in the Journal of Medicinal Chemistry reported that this compound exhibits potent anti-inflammatory properties by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6.

Beyond its anti-inflammatory effects, methyl 4-hydroxyisoquinoline-3-carboxylate has also been investigated for its potential as an antioxidant. Oxidative stress is a key factor in the pathogenesis of many diseases, including neurodegenerative disorders and cardiovascular diseases. Research conducted at the University of California, Los Angeles (UCLA) found that this compound effectively scavenges free radicals and protects cells from oxidative damage. These findings suggest that it could be a valuable candidate for the development of neuroprotective drugs.

The structural features of methyl 4-hydroxyisoquinoline-3-carboxylate also make it an attractive target for chemical modifications aimed at enhancing its biological activity or improving its pharmacokinetic properties. For example, the hydroxyl group can be derivatized to introduce additional functional groups that may enhance solubility or target specificity. Similarly, the carboxylate ester moiety can be modified to improve metabolic stability or reduce toxicity.

In addition to its pharmaceutical applications, methyl 4-hydroxyisoquinoline-3-carboxylate has found use in materials science due to its ability to form stable complexes with metal ions. These complexes exhibit unique optical and electronic properties, making them suitable for applications in sensors, catalysts, and electronic devices. A study published in the Journal of Materials Chemistry C demonstrated that metal complexes derived from this compound show enhanced luminescence properties and can be used as efficient luminescent probes for detecting specific analytes.

The safety profile of methyl 4-hydroxyisoquinoline-3-carboxylate has been extensively evaluated through various toxicological studies. These studies have shown that the compound is generally well-tolerated at therapeutic doses and does not exhibit significant cytotoxicity or genotoxicity. However, as with any new chemical entity, further research is needed to fully understand its long-term safety and potential side effects.

In conclusion, methyl 4-hydroxyisoquinoline-3-carboxylate (CAS No. 1108146-90-2) is a multifaceted compound with a wide range of potential applications in pharmaceuticals, materials science, and chemical synthesis. Its unique chemical structure and biological activities make it a valuable target for further research and development. As ongoing studies continue to uncover new insights into its properties and mechanisms of action, it is likely that this compound will play an increasingly important role in advancing our understanding of complex biological processes and developing innovative solutions to pressing health challenges.

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