Harvey I. Skulnick

Stereochemical control as a function of protecting-group participation in 2-deoxy-D-erythro-pentofuranosyl nucleosides☆

Abstract Possible features controlling the anomeric ratios in the synthesis of the antiviral antibiotic dihydro-5-azathymidine have been examined. Replacement of the 3- and 5-(4-methylbenzoyl) protecting groups in 2-deoxy- D - erythro -pentofuranosyl chloride by benzyl groups led to changes in anomeric ratios in stannic chloride-mediated condensations with both 5-methyl-2,4-bis(trimethylsilyl)triazine and 2,4-bis(trimethylsilyl)thymine. Analysis of the results suggested that steric elements, and more importantly, participating factors, of both the 3- and 5-protecting groups affect the anomeric ratios.

Synthesis and pharmacological evaluation of sulfone substituted HIV protease inhibitors

Abstract The sulfonamide substituted pyranones ( 1 ) have recently been shown to be potent HIV protease inhibitors. We prepared a series of sulfone substituted analogs and compared their biological activities to those of the corresponding sulfonamide analogs. It was determined that although these compounds maintained activity as enzyme inhibitors, they showed somewhat diminished antiviral activity even though they may possess increased membrane permeability.