SZÜČOVÁ, Lucie, SPÍCHAL, Lukáš, DOLEŽAL, Karel, ZATLOUKAL, Marek, GREPLOVÁ, Jarmila, GALUSZKA, P., KRYŠTOF, Vladimír, VOLLER, Jiří, POPA, Igor, MASSINO, F.J., JORGENSEN, J.E., STRNAD, Miroslav. Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives. Bioorganic & Medicinal Chemistry. 2009, 17(5), 1938-1947. ISSN 0968-0896. E-ISSN 1464-3391

In an attempt to improve specific biological functions of cytokinins routinely used in plant micropropagation, thirty-three 6-benzylamino-9-tetrahydropyran-2-ylpurine (THPP) and 9-tetrahydrofuran-2-ylpurine (THFP) derivatives were prepared. The new derivatives were prepared by condensation of 6-chloropurine with 3,4-dihydro-2H-pyran or 2,3-dihydrofuran and then by the condensation with the corresponding benzylamines. The prepared compounds were characterized by elemental analyses, TLC, HPLC, melting point determinations, CI+ MS and 1H NMR spectroscopy. The cytokinin activity of all the prepared derivatives was assessed in three classical cytokinin bioassays as well as receptor assay. Subsequently, the susceptibility of several new derivatives to enzyme degradation was studied. To provide a practical perspective, , the pH stability and cytotoxicity of the prepared compounds against human diploid fibroblasts and the human cancer cell lines K-562 and MCF-7 was also assayed.