Synthesis of Novel Thiopurine Pyranonucleosides: Evaluation of Their Bioactivity |
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| Authors: | Athina Dimopoulou Stella Manta Vanessa Parmenopoulou Petros Gkizis Evdoxia Coutouli-Argyropoulou Dominique Schols |
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| Affiliation: | 1. Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa, Greece;2. Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki, Greece;3. Department of Microbiology and Immunology, Rega Institute for Medical Research, KU Leuven, Leuven, Belgium |
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| Abstract: | ![]()
We report the synthesis of novel thiopurine pyranonucleosides. Direct coupling of silylated 6-mercaptopurine and 6-thioguanine with the appropriate pyranoses 1a–e via Vorbrüggen nucleosidation, gave the N-9 linked mercaptopurine 2a–e and thioguanine 4a–e nucleosides, while their N-7 substituted congeners 10a–e and 7a–e, were obtained through condensation of the same acetates with 6-chloro and 2-amino-6-chloropurines, followed by subsequent thionation. Nucleosides 3a–e, 5a–e, 8a–e, and 11a–e were evaluated for their cytostatic activity in three different tumor cell proliferative assays. |
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| Keywords: | 6-Mercaptopurine 6-thioguanine 6-chloropurine 2-amino-6-chloropurine pyranonucleosides cytotoxic activity |
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