Halophenyl furanopyrimidines as potent and selective anti-VZV agents.

Bicyclic furano pyrimidines have been previously reported by us to be highly potent and selective inhibitors of varicella zoster virus (VZV). p-Alkyl phenyl analogues are particularly potent with EC50 values below 1 nM. In this article we report the synthesis and anti-VZV activity of a series of halophenyl analogues, with variation in the nature (F, Cl, Br) and location (o, m, p) of the halogen substituent.

Upon the intriguing stereoselective formation of organobismuth(V) complexes.

The preparation of triphenylbismuth(V) 3a-k and antimony(V) 4e-k bis-carboxy ester complexes is described. A range of studies in solution suggest that the diastereoselective formation of (RR,SS)-3a-j is governed by the thermodynamic stability of rapidly interconverting epimeric species. Diastereoselectivity is absent in the case of the corresponding Sb complexes, leading to the conclusion that a combination of both ligand-ligand (steric) and metal-ligand (hyperconjugative) interactions govern stereoselectivity.

Bicyclic furo pyrimidine nucleosides with aryloxyphenyl and halophenyl substituted side chains as potent and selective varicella-zoster virus inhibitors.

The discovery of potent and selective inhibitors of VZV based on unusual bicyclic alkyl furo pyrimidine nucleosides has been recently reported. Modifications to the side-chain by addition of a phenyl group were found to further enhance the antiviral potency of these compounds. A series of alkoxyphenyl compounds (5a-5g) and two halophenyl derivatives (5h and 5i) were successfully synthesised and displayed anti-VZV activity at low microM concentrations.

Furano pyrimidines as novel potent and selective anti-VZV agents.

Bicyclic furano pyrimidine nucleosides have been found to be highly potent and selective inhibitors of varicella zoster virus (VZV). They are inactive against herpes simplex virus and have been known for several decades as (unwanted) synthetic by-products in the Pd-catalysed coupling of acetylenes to 5-iodo nucleosides. These fluorescent bicyclic nucleosides are now established as a new family of potent antivirals.