European Journal of Organic Chemistry · 2009 · 16 citations · 42 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryStructure-activity RelationshipsSynthetic Medicinal ChemistryEnzyme InhibitionStructure-activity Relationship AnalysisBiological Evaluation ReportChemical Synthesis Of AnaloguesNucleoside Analog SynthesisNucleoside AnalogsNucleoside Reverse Transcriptase InhibitorsThiazole Chemistry
Abstract Novel pseudonucleosides 3 and 4 bearing a thiazolidin‐4‐one moiety were firstly synthesized by a one‐pot, multicomponent, tandem Staudinger/aza‐Wittig/intermolecular nucleophilic addition/intramolecular cyclization process in good yields of 43.8–88.0 %. Deacetylation of 3 and 4 afforded compounds 5 and 6 , respectively. The structures of the new compounds were determined on the basis of the X‐ray crystal structures of 3b and 3e and by 1 H and 13 C NMR spectroscopy and high‐resolution mass spectrometry. The antitumor activity and the inhibitory activities against glycosidases and HIV reverse transcriptase of 5 and 6 were also evaluated.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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