anthranilatebased

Anthranilate‑based compounds are a class of organic molecules derived from anthranilic acid, also known as 2‑aminobenzoic acid. The core structure consists of a benzene ring bearing an amino group at the ortho position relative to a carboxyl group. Substitutions on the aromatic ring or modifications of the amino or carboxyl functionalities generate a diverse range of derivatives with varied physicochemical properties.

In chemistry, anthranilate derivatives serve as key intermediates in the synthesis of pharmaceuticals, agrochemicals, dyes, and fragrances. Notable examples include the antimalarial drug proguanil, the antihistamine pheniramine, and the insect repellent N‑ethyl‑m‑toluic acid anthranilate. In the fragrance industry, methyl anthranilate imparts a grape‑like aroma and is employed in flavoring formulations.

The biological relevance of anthranilic acid stems from its role as a precursor in the shikimate pathway, where it participates in the biosynthesis of tryptophan and related indole alkaloids in plants and microorganisms. Consequently, anthranilate‑based inhibitors are explored as antimicrobial agents that target enzymes such as anthranilate synthase.

Physical properties of anthranilate derivatives typically include moderate polarity, limited water solubility, and aromatic UV absorption, which facilitate analytical detection by chromatography or spectroscopy. Safety assessments indicate that many compounds in this group exhibit low acute toxicity, though some may cause irritation or sensitization upon prolonged exposure; handling guidelines recommend protective equipment and adequate ventilation.

Research continues to expand the utility of anthranilate‑based structures, particularly in drug discovery where their scaffold can be tuned to modulate receptor affinity, metabolic stability, and pharmacokinetic profiles.