Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides: Application of the Suzuki−Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids

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Abstract
The Suzuki−Miyaura reaction of protected 6-chloropurine and 2-amino-6-chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6 − 9. Their deprotection yielded a series of substituted 6-phenylpurine bases and nucleosides 10 − 13. Significant cytostatic activity (IC50 0.25−20 μmol/L) in CCRF-CEM, HeLa, and L1210 cell lines was found for several 6-(4-X-substituted phenyl)purine ribonucleosides 12 (X = H, F, Cl, and OR), while the 6-phenylpurine and 2-amino-6-phenylpurine bases 10 and 11, as well as 2-amino-6-phenylpurine ribosides 13, were entirely inactive against these cell lines.

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