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

The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6-chlor opurine bases and nucleosides with substituted phenylboronic acids led to t he corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Th eir deprotection yielded a series of substituted 6-phenylpurine bases and n ucleosides 10-13. Significant cytostatic activity (IC50 0.25-20 mu mol/L) i n CCRF-CEM, HeLa, and L1210 cell lines was found for several 6-(4-X-substit uted phenyl)purine ribonucleosides 12 (X = H, F, Cl, and OR), while the 6-p henylpurine and 2-amino-6-phenylpurine bases 10 and 11, as well as 2-amino- 6-phenylpurine ribosides 13, were entirely inactive against these cell line s.