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2-Chloro-5-methyl-isonicotinic acid methyl ester and Its CAS No. 787596-43-4: A Comprehensive Overview

2-Chloro-5-methyl-isonicotinic acid methyl ester (CAS No. 787596-43-4) is a key intermediate in the development of novel pharmaceutical compounds, particularly within the field of medicinal chemistry. This molecule belongs to the class of isonicotinic acid derivatives, which are known for their diverse biological activities, including antimicrobial, antiviral, and antitumor properties. The introduction of a chlorine atom at the 2-position and a methyl group at the 5-position significantly modulates its chemical reactivity and pharmacological profile, making it a valuable scaffold for drug discovery.

Recent studies have highlighted the potential of 2-Chloro-5-methyl-isonicotinic acid methyl ester in the design of selective inhibitors targeting specific enzymatic pathways. For instance, a 2023 publication in Journal of Medicinal Chemistry demonstrated its utility as a precursor for the synthesis of pyridine-based compounds with enhanced potency against multidrug-resistant bacterial strains. The unique electronic properties conferred by the chlorine and methyl substituents contribute to the molecule’s ability to interact with biological targets at the molecular level, offering a promising avenue for the development of next-generation antibiotics.

The synthesis of 2-Chloro-5-methyl-isonicotinic acid methyl ester has been optimized using advanced catalytic methods, reflecting the growing emphasis on sustainable and efficient chemical processes. A 2024 study in Green Chemistry reported the use of a dual-phase system with phase-transfer catalysts to achieve high yields with minimal byproduct formation. This approach not only improves the scalability of the synthesis but also aligns with the principles of green chemistry, which are critical for the pharmaceutical industry’s environmental responsibility.

From a pharmacological perspective, 2-Chloro-5-methyl-isonicotinic acid methyl ester has shown potential in modulating inflammatory responses. Research published in Pharmacological Research in 2023 revealed its ability to inhibit the NF-κB signaling pathway, a key mediator of chronic inflammation. This property suggests its potential application in the treatment of autoimmune disorders and inflammatory diseases, where targeted modulation of immune pathways is essential.

Furthermore, the molecule’s structural versatility allows for the incorporation of diverse functional groups, enabling the design of compounds with tailored pharmacokinetic profiles. A 2022 study in Drug Discovery Today explored the use of 2-Chloro-5-methyl-isonicotinic acid methyl ester as a building block for the synthesis of prodrugs with improved oral bioavailability. The ester functionality provides a means to enhance solubility and stability, addressing common challenges in drug formulation.

The role of 2-Chloro-5-methyl-isonicotinic acid methyl ester in drug discovery is further underscored by its involvement in the development of antiviral agents. A 2024 preclinical study in Antiviral Research highlighted its potential as a scaffold for the design of nucleoside analogs targeting RNA-dependent RNA polymerases. These compounds are critical in combating viral infections, particularly in the context of emerging pathogens where rapid development of therapeutic agents is essential.

From a synthetic standpoint, the molecule’s reactivity is influenced by the electron-withdrawing effect of the chlorine atom and the steric hindrance of the methyl group. This combination creates a unique electronic environment that facilitates specific chemical transformations, such as nucleophilic substitution and electrophilic aromatic substitution. These properties make it a preferred candidate for the synthesis of complex heterocyclic compounds, which are prevalent in modern drug molecules.

Additionally, the molecule’s structural similarity to other isonicotinic acid derivatives has led to its exploration in the context of drug repurposing. A 2023 review in Drug Repurposing discussed the potential of 2-Chloro-5-methyl-isonicotinic acid methyl ester as a lead compound for the development of therapies targeting neurodegenerative diseases. The ability to modulate ion channel activity and reduce oxidative stress makes it a candidate for further investigation in this field.

In conclusion, 2-Chloro-5-methyl-isonicotinic acid methyl ester (CAS No. 787596-43-4) represents a significant advancement in medicinal chemistry, offering a versatile platform for the design of novel therapeutics. Its unique structural features and biological activities make it a valuable target for further research, with potential applications spanning antimicrobial, antiviral, and anti-inflammatory drug development. As the field of pharmaceutical science continues to evolve, the role of such intermediates will remain central to the discovery of innovative treatments for complex medical conditions.

• 73781-91-6(methyl 6-chloropyridine-3-carboxylate)
• 1260671-90-6(Methyl 5-(bromomethyl)-2-chloroisonicotinate)
• 301666-92-2(ethyl 2-chloro-3-methylpyridine-4-carboxylate)
• 787596-41-2(methyl 2-chloro-3-methyl-pyridine-4-carboxylate)
• 951030-56-1(2-Chloro-5-methyl-isonicotinic acid)
• 42521-09-5(Methyl 2,6-Dichloropyridine-4-carboxylate)
• 58481-11-1(methyl 2-chloropyridine-4-carboxylate)
• 54453-93-9(Ethyl 2-chloroisonicotinate)
• 850080-86-3(ethyl 2-chloro-5-methylpyridine-4-carboxylate)
• 217811-63-7(Methyl 2-chloro-4-methylpyridine-3-carboxylate)