Bile acids have a multitude of pharmacological properties; in the commonest therapeutic employ ursodeoxycholic acid (UDCA) or its hepatic metabolites, glyco- and tauroursodeoxycholic acids (GUDCA and TUDCA) are used in the treatment of cholestatic liver disease and to promote the dissolution of cholesterol gallstones. These compounds may be administered safely to patients suffering from altered cholesterol synthesis and metabolism. Their amphiphilic character generally enhances cell membrane permeability, moreover it improves the absorption of hydrophobic molecules and the delivery of drugs that specifically target the liver. The recent discovery of new potential therapeutic applications of bile acid derivatives has rekindled the interest of the scientific community and pharmaceutical industry in the synthesis of new analogs. Both microwave (MW) and high-intensity ultrasound (HIU) have emerged as important promoters of organic reactions. While microwave irradiation has already been exploited to promote chemical modifications of bile acids, we did found no report of such reactions having been carried out under HIU. The enhanced reactivity, peculiar regioselectivities and consistent reduction of reaction times that can be promoted by either method prompted us to an investigation employing these methods.
CHEMICAL MODIFICATIONS OF BILE ACIDS PROMOTED BY MICROWAVE OR HIGH-INTENSITY ULTRASOUND.
BOFFA, Luisa;CRAVOTTO, Giancarlo;
2004-01-01
Abstract
Bile acids have a multitude of pharmacological properties; in the commonest therapeutic employ ursodeoxycholic acid (UDCA) or its hepatic metabolites, glyco- and tauroursodeoxycholic acids (GUDCA and TUDCA) are used in the treatment of cholestatic liver disease and to promote the dissolution of cholesterol gallstones. These compounds may be administered safely to patients suffering from altered cholesterol synthesis and metabolism. Their amphiphilic character generally enhances cell membrane permeability, moreover it improves the absorption of hydrophobic molecules and the delivery of drugs that specifically target the liver. The recent discovery of new potential therapeutic applications of bile acid derivatives has rekindled the interest of the scientific community and pharmaceutical industry in the synthesis of new analogs. Both microwave (MW) and high-intensity ultrasound (HIU) have emerged as important promoters of organic reactions. While microwave irradiation has already been exploited to promote chemical modifications of bile acids, we did found no report of such reactions having been carried out under HIU. The enhanced reactivity, peculiar regioselectivities and consistent reduction of reaction times that can be promoted by either method prompted us to an investigation employing these methods.
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