title: Synthesis and cytotoxic evaluation of novel pyrimidine deoxyapiothionucleosides.
abstract: The synthesis of novel pyrimidine deoxyapiothionucleosides of D- and L-series was realized following application of a versatile and high-yielding scheme, which utilized inexpensive L- and D-arabinose as starting materials, respectively, and which makes use of a regio- and stereo-selective Pummerer rearrangement reaction for the coupling of the nucleobase with the thiosugar moiety. Some of the targeted compounds have shown selective cytotoxic effects (with IC50<10 μM) against specific cancer cell lines. All of the tested compounds had no cytotoxic effect on the normal cell line tested.
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 541 24, Greece.
authors.forename: Stefanos S
authors.initials: SS
authors.lastname: Kotoulas
authors.forename: Vesna V
authors.initials: VV
authors.lastname: Kojić
authors.forename: Gordana M
authors.initials: GM
authors.lastname: Bogdanović
authors.forename: Alexandros E
authors.initials: AE
authors.lastname: Koumbis
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D001089:Arabinose / Q000737:chemistry; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D011743:Pyrimidines / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013872:Thionucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity
chemical_list: D000970:Antineoplastic Agents; D011743:Pyrimidines; D013872:Thionucleosides; D001089:Arabinose; C030986:pyrimidine