Synthesis and antiviral activity of new substituted methyl [2-(arylmethylene-hydrazino)-4-oxo-thiazolidin-5-ylidene]acetates

Abstract

A series of new methyl [2-(arylmethylene-hydrazono)-4-oxo-thiazolidin-5-ylidene]acetates (5a-o) were synthesized via cyclocondensation of thiosemicarbazones (3a-o) with dimethyl but-2-ynedioate (4) in good yields under solvent-free conditions. The environmentally friendly solvent-free protocol overcomes the limitations associated with the customary protracted solution phase synthesis and afforded the title compounds in a few minutes. Compounds 5b-i and 5h-o were evaluated for their antiviral activity against the replication activity of HIV-1 and HIV-2 in MT-4 using the MTT assay. The same compounds were also evaluated in vitro for their selective antiviral activity against hepatitis C virus (HCV) in the Huh 5-2 replicon system (type 1b, Con1 strain).

Keywords: Anti-HCV activity; Anti-HIV activity; Non-nucleoside inhibitors (NNRTIs); Thiazolidin-4-ones.