Synthesis of anionic derivatives of myo-inositol and other polyols and investigation of their antiviral activity

The search for new, effective antiviral agents currently includes assessment of polyanionic compounds of various structures; these are highly active inhibitors of viral penetration into cells. The present report describes the preparation of phosphate and sulfate derivatives based on 2,3,4,5-tetra-O-benzyl-D,L-iditol, 1,12-dodecanediol, and a dimeric analog of inositol-containing phospholipids. The dimeric derivative, which contains two myo-inositol cyclitol rings linked by a single hydrophobic fragment, was synthesized at high yield using the H-phosphonate method. The antiviral activity of the series of compounds synthesized here was assessed against a panel of viruses. All were inactive against rhinoviruses; the disulfate of tetra-O-benzyl-D,L-iditol inhibited Coxsackie virus and had the greatest cytotoxicity; the disulfate of 1,2-dodecanediol was inactive against all viruses, while the diphosphate of 2,3,4,5-tetra-O-benzyl-D,L-iditol and the monosulfate of 1,2-dodecanediol were active against herpes simplex viruses types 1 and 2. __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 42, No. 1, pp. 6–12, January, 2008.