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Effects of lipophilicity, protecting group and stereochemistry on the antimalarial activity of carbohydrate-derived thiochromans

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A series of novel carbohydrate-derived thiochromans has been successfully synthesized in order to investigate the influence of alkyl substituents on the aromatic ring of the thiophenol moiety in addition to… Click to show full abstract

A series of novel carbohydrate-derived thiochromans has been successfully synthesized in order to investigate the influence of alkyl substituents on the aromatic ring of the thiophenol moiety in addition to the effect of protecting groups and stereochemistry on the sugar component of the target molecules. Results from the evaluation of the thiochromans for their antimalarial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum suggest that the presence of short chain alkyl substituents, a benzyl ether protecting group and equatorial orientation of the C-4 substituent on the sugar moiety are crucial structural features that impart high antimalarial activity.

Keywords: carbohydrate derived; protecting group; antimalarial activity; derived thiochromans; activity

Journal Title: Medicinal Chemistry Research
Year Published: 2017

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