benzo[d]thiazole-4-carboxylic acid

Benzo[d]thiazole-4-carboxylic acid (CAS 1260529-67-6) is a heterocyclic aromatic compound belonging to the benzothiazole family — a fused bicyclic system consisting of a benzene ring fused to a thiazole ring. The molecular formula is C₈H₅NO₂S with a molecular weight of 179.2 g/mol, and the compound is supplied as an off-white to light yellow solid at purities of ≥95% up to ≥98.0%.

In medicinal chemistry, benzo[d]thiazole-4-carboxylic acid has emerged as a privileged pharmacophore. The benzothiazole core is recognized for a wide range of biological activities, and the 4‑carboxylic acid substitution pattern provides an additional handle for derivatization, enabling the synthesis of amides, esters, and other derivatives with optimized target engagement and physicochemical properties.

The compound has been identified as a potent inhibitor of two clinically relevant targets. First, benzo[d]thiazole-4-carboxylic acid and its derivatives exhibit potent inhibitory activity against Mycobacterium tuberculosis by targeting the DprE1 enzyme, which plays a crucial role in the cell wall biosynthesis of the pathogen. By binding to the ATP-binding pocket of the GyrB subunit, the compound inhibits the enzyme‘s function, disrupting cell wall integrity and leading to bacterial death. [5†L9-L21] Second, the compound has been validated as a potent inhibitor of dihydroorotate dehydrogenase (DHODH), an enzyme that catalyzes the conversion of dihydroorotate to orotic acid in pyrimidine biosynthesis. DHODH inhibitors are being investigated for cancer treatment, and benzo[d]thiazole-4-carboxylic acid has shown efficacy against human cancer cell lines in both in vitro and in vivo models.

Beyond pharmaceutical applications, benzo[d]thiazole-4-carboxylic acid serves as a versatile building block in organic synthesis, as a ligand in coordination chemistry and catalysis, and as a precursor for the development of advanced organic materials such as dyes and fluorescent markers, leveraging its electron-accepting thiazole ring and the functional handle of the carboxylic acid group.

Product Parameters

Quality Assurance at Cosperpharm

Each batch undergoes:

● Gas chromatography (GC) – purity ≥97.0%

● Non‑aqueous titration – purity ≥97.0%

● Refractive index – confirmatory analysis

● ¹H NMR – structural verification

● Appearance – colorless to light yellow to light orange clear liquid

A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.

Why Cosperpharm? – Our Competitive Advantages

Product Advantages

1. Dual enzyme inhibition (DprE1 + DHODH)

Benzo[d]thiazole-4-carboxylic acid is a rare, multi-target pharmacophore that simultaneously inhibits DprE1 (a validated anti-tubercular target essential for M. tuberculosis cell wall synthesis) and DHODH (a key enzyme in pyrimidine biosynthesis relevant to cancer therapy). This dual mechanism positions the scaffold for both infectious disease and oncology research.

2. Potent anti-tubercular activity

Derivatives of benzo[d]thiazole-4-carboxylic acid have shown potent inhibitory activity against Mycobacterium tuberculosis with improved inhibitory concentrations compared to standard drugs such as Isoniazid (INH) and Rifampicin (RIF). The compound binds to the DprE1 enzyme, disrupting cell wall biosynthesis and leading to bacterial death.

3. Anti-cancer DHODH inhibition

The compound has been validated as a potent inhibitor of dihydroorotate dehydrogenase (DHODH), an enzyme that plays a critical role in pyrimidine biosynthesis, and has shown efficacy against human cancer cell lines in both in vitro and in vivo models. Computational methods, including pharmacophore modeling and molecular docking simulations, have confirmed these properties. DHODH inhibitors are being explored for the treatment of hematological malignancies and other cancers.

4. Broad-spectrum biological activity

Beyond its anti-tubercular and anti-cancer properties, benzo[d]thiazole-4-carboxylic acid has been reported for use as a fungicide, anti‑malarial, anti‑convulsant, insecticide, sedative, anti‑inflammatory drug, and for treating diabetes, demonstrating the remarkable versatility of this benzothiazole pharmacophore.

5. Versatile synthetic building block

The carboxylic acid group at the 4-position of the benzothiazole core serves as a functional handle for facile derivatization into amides, esters, and other conjugates, enabling rapid generation of focused libraries for structure‑activity relationship (SAR) studies.

6. Materials science utility

The compound is investigated in the development of organic ligands for catalysis and in the synthesis of advanced organic materials, such as dyes and fluorescent markers, leveraging the electron-accepting nature of the thiazole ring combined with the functional handle of the acid group for tailored electronic and optical characteristics.

7. Conformational rigidity

The fused aromatic, bicyclic structure of the benzothiazole core provides conformational rigidity, which can reduce the entropic penalty upon binding to biological targets, improving potency and selectivity in drug discovery applications.

8. High purity

Standard ≥95% ensures reliable results in sensitive research applications; ≥98% purity grade available upon request

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