2-Amino-3-methoxybenzoic Acid (CAS: 3177-80-8), also known by its synonyms such as 3-Methoxyanthranilic acid or O-Anisidine-6-carboxylic acid, stands as a pivotal chemical compound in various scientific and industrial domains. With a molecular formula of C8H9NO3 and a molecular weight of 167.16, this compound is recognized for its distinctive chemical structure and reactivity, making it an indispensable building block for complex molecules.

This compound typically presents as a white powder or crystalline solid, distinguished by its melting point of 169-170 °C and a boiling point estimated around 333.9±27.0 °C. Its density is approximately 1.303±0.06 g/cm3, and it exhibits slight solubility in common solvents like DMSO and methanol. These precise physical and chemical properties ensure its reliability and consistency across a multitude of applications, from laboratory research to large-scale industrial processes.

One of the most significant applications of 2-Amino-3-methoxybenzoic Acid lies within the pharmaceutical industry. It serves as a crucial intermediate in the synthesis of vital medicinal compounds. For instance, it is integral to the preparation of CDK1/cyclin B inhibitors, which are actively explored for their potential in antitumor treatment. Furthermore, it plays a key role in the synthesis of Alogliptin, a well-known inhibitor of dipeptidyl peptidase, critical for lowering blood-glucose levels and thus invaluable in the management and potential treatment of diabetes. Beyond these, its derivatives have shown promise in the discovery and optimization of highly potent phosphatidylinositol 3-kinase (PI3K) inhibitors for cancer therapy, as well as novel sulfonamide-bearing methoxyquinazolinone derivatives acting as anticancer and apoptosis-inducing agents. It has also been implicated in the synthesis of compounds used in antidepressant research and 18F-labeled radiotracers for advanced in vivo imaging with positron emission tomography (PET).

Beyond its direct pharmaceutical roles, 2-Amino-3-methoxybenzoic Acid functions as a highly versatile chemical intermediate in general organic synthesis and research and development. Its reactivity, particularly its ability to participate in nucleophilic aromatic substitution reactions, allows for the precise introduction of specific functional groups into molecular structures. This makes it a valuable asset for diversifying chemical libraries and exploring complex structure-activity relationships. Researchers utilize it as a fundamental building block for a wide array of organic compounds, including novel textile dyes obtained through enzymatic transformations, and in advanced techniques such as benzyne click chemistry.

Moreover, this compound exhibits interesting biological activities, including antioxidative properties. It has been shown to inhibit the conversion of picolinic acid to kynurenine in vitro, and significantly inhibits the formation of 3-hydroxyanthranilic acid and xanthurenic acid from anthranilic acid. These inhibitory effects underscore its potential in various biological and biochemical studies, contributing to a deeper understanding of metabolic pathways and therapeutic interventions.

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