Benzothiazole-Based Six- and Seven-Membered Heterocycles: A Critical Review of Synthetic Approaches and Pharmacological Applications
DOI:
https://doi.org/10.64354/tag7a881Keywords:
benzothiazole; benzothiazepine; fused heterocycles; heterocyclic synthesis; structure–activity relationship; anticancer agents; green chemistryAbstract
Benzothiazole is among the most heavily exploited bicyclic scaffolds in medicinal chemistry. Its planar, π-deficient framework combines a hydrogen-bond-accepting ring nitrogen with a polarisable sulfur atom, and it appears in agents as diverse as riluzole, pramipexole, the amyloid tracer Pittsburgh Compound B and the antitumour prodrug Phortress. This review examines the chemistry and pharmacology of benzothiazoles carrying, or fused to, six- and seven-membered heterocyclic rings. The routes available for constructing the benzothiazole nucleus itself are surveyed first, from the condensation of 2-aminothiophenol with carboxylic acids and aldehydes and the oxidative cyclisation of thioanilides, to copper- and palladium-catalysed C–S bond-forming and C–H functionalisation cyclisations and visible-light photoredox methods. Annulation of six-membered rings, principally the pyrimido[2,1-b]benzothiazoles and related fused pyrimidines and thiazines, is then considered alongside the classical named reactions used to assemble them. The seven-membered series is dominated by the 1,5-benzothiazepines, a scaffold represented in clinical use by diltiazem, and the review covers the chalcone route to this ring system together with ring-closing metathesis, ring expansion and, more recently, biocatalytic approaches. Enabling technologies that cut across both ring classes, including microwave and ultrasound activation, aqueous and ionic-liquid media, solvent-free protocols and multicomponent reactions, are assessed against the green-chemistry claims commonly made for them. The pharmacological sections treat anticancer activity, with emphasis on the 2-arylbenzothiazole series that produced Phortress, together with kinase inhibition, antimicrobial and antimycobacterial activity, anti-inflammatory and antioxidant behaviour, and inhibition of carbohydrate-processing enzymes. Structure–activity relationships and the principal obstacles to further development, chiefly aqueous solubility, selectivity and metabolic liability, are examined in the final sections.
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