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Benzothiophenes (also known as benzothiofuran; thianaphthene) are bicyclic aromatic heterocycles in which a benzene ring is fused to a thiophene ring. Occurring in natural deposits, it finds use in the synthesis of other heterocyclic compounds. It is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. For example, the nitration of benzothiophene gives a mixture of five products.
It is used as starting material for the synthesis of bioactive molecules. The core structure is a part of various pharmaceutical substances and natural products. For example, zileuton is an orally active inhibitor of 5-lipoxygenase, indicated for maintenance treatment of asthma. The core is also part of an estrogen receptor modulator namely Raloxifine which inhibits the effect of estrogen on uterus. It is also used in the manufacturing of dyes such as thioindigo.