title: 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).
authors.affiliation: Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan. aamersaeed@yahoo.com
authors.forename: Aamer
authors.initials: A
authors.lastname: Saeed
authors.forename: Najim A
authors.initials: NA
authors.lastname: Al-Masoudi
authors.forename: Muhammad
authors.initials: M
authors.lastname: Latif
mesh_terms: D000085:Acetates / Q000138:chemical synthesis* / Q000494:pharmacology*; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D015195:Drug Design; D015497:HIV-1 / Q000187:drug effects / Q000254:growth & development; D015498:HIV-2 / Q000187:drug effects / Q000254:growth & development; D016174:Hepacivirus / Q000187:drug effects / Q000254:growth & development; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000085:Acetates; D019380:Anti-HIV Agents; D000998:Antiviral Agents; D053778:Thiazolidines
keywords: Anti-HCV activity; Anti-HIV activity; Non-nucleoside inhibitors (NNRTIs); Thiazolidin-4-ones