Applications of the Benzofuran and Benzothiophene Ring, Chemistry tutorial

Introduction:

Being heterocyclic compounds, benzofuran and benzothiophene find utilization in research as starting materials for the synthesis of larger, generally bioactive structures. They are mainly found within the chemical structures of pharmaceutical drugs like amiodarone, raloxifene, zileuton and sertaconazole. Benzothiophene is as well employed in the manufacturing of dyes like thioindigo.

Amiodarone:

Amiodarone (figure shown below) is the antiarrhythmic agent (medication employed for irregular heart beat), used for different kinds of tachyarrhythmias (that is, fast forms of irregular heart beat), both ventricular and supraventricular (atrial) arrhythmias. Discovered in the year 1961, it was not approved for use in the United States until the year 1985. In spite of comparatively common side-effects, it is employed in arrhythmias that are or else difficult to treat by medication. Related newer compounds, like dronedarone that have the benzofuran ring system, have lower efficiency. However they have reduced rate of side-effects. It includes the benzofuran ring system.

126_Structure of Amiodarone.jpg

Fig: Structure of Amiodarone

Sertaconazole:

Sertaconazole nitrate (Ertaczo, Dermofix) is the antifungal medication of the Imidazole class. This is available as a cream to treat skin infections like athlete's foot. It comprises the benzothiophene ring system.

1472_Setraconazole.jpg

Fig: Setraconazole

Raloxifene:

Raloxifene (that is, marketed as Evista by Eli Lilly and Company) is an oral selective estrogen receptor modulator (SERM) which consists of estrogenic actions on bone and anti-estrogenic actions on the uterus and breast. This is employed in the prevention of osteoporosis in the postmenopausal women. 

In the year 2006, the National Cancer Institute announced that raloxifene was as efficient as tamoxifen in reducing the incidence of breast cancer in postmenopausal women at increased risk. The main adverse effect of tamoxifen is uterine cancer; raloxifene had fewer uterine cancers. Tamoxifen raised the risk of cataracts, however raloxifene didn't. Both the groups had more blood clots in veins and the lungs; however that side effect was more common by the tamoxifen as compare to raloxifene. On September 14, 2007, the U.S. Food and Drug Administration announced approval of raloxifene for reducing the risk of invasive breast cancer in the postmenopausal women by osteoporosis and in postmenopausal women at high risk for invasive breast cancer. 

Raloxifene hydrochloride (HCl) comprises the empirical formula C28H27NO4S•HCl, that corresponds to a molecular weight of 510.05 g/mol. Raloxifene HCl is an off-white to pale-yellow solid which is slightly soluble in water. Its synthesis is illustrated in the figure below.

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Fig: Synthesis of Raloxifene

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