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  • Synthesis of novel thiopurine pyranonucleosides: evaluation of their bioactivity.

Synthesis of novel thiopurine pyranonucleosides: evaluation of their bioactivity.

Nucleosides, nucleotides & nucleic acids (2015-03-17)
Athina Dimopoulou, Stella Manta, Vanessa Parmenopoulou, Petros Gkizis, Evdoxia Coutouli-Argyropoulou, Dominique Schols, Dimitri Komiotis
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methanol-d4, 99 atom % D
Sigma-Aldrich
Methanol-d4, "100%", 99.96 atom % D
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D
Sigma-Aldrich
Methanol-d4, anhydrous, ≥99.8 atom % D
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, anhydrous
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, "100%", 99.95 atom % D
Sigma-Aldrich
Methanol-d4, "100%", ≥99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D
Sigma-Aldrich
Methanol-d4, ≥99.8 atom % D, contains 0.05 % (v/v) TMS