Synthesis and biological activities of O6-alkylguanine derivatives

Abstract

The synthesis of some biologically active O⁶-alkylguanine derivatives was achieved by alkoxylation of 2-amino-6-chloropurine with sodium alkoxides in polar aprotic solvent (DMSO) conditions. The starting material 2-amino-6-chloropurine was prepared by chlorination of 2,9-diacetylguanine (obtained from acetylation of commercially available guanine) by PEG-2000 phase transfer catalysis. The structures of the products were deduced from elemental analysis and spectral data (IR, ¹H NMR, and mass spectra). All the title compounds were screened for their antifungal activities, and some of the compounds showed promising activities.

KEY WORDS: O⁶-Alkylguanine derivatives, 2-Amino-6-chloropurine, Synthesis, Fungicidal activity

Bull. Chem. Soc. Ethiop. 2010, 24(3), 425-432.