[Synthesis and biological activity of derivatives of guanosine 3', 5'-cyclic phosphate]

Methyl, n-butyl 2'-TBDMS-N2-DMF-guanosine 3',5'-cyclic phosphate and 2'-TBDMS-N2-DMF-guanosine 3',5'-cyclic diethyl-phosphoramidate were synthesized by reaction of protected guanosine with trivalent phosphorus reagents in the presence of tetrazole followed by oxidation. The reaction occurred stereospecifically. Protected guanosine 3',5'-cyclic phosphotriesters and N, N'-diethyl-phosphoramidate were shown to have inhibitory activity on the synthesis of DNA and RNA in mouse liver tumor cell. Diastereoisomers of n-butyl N2-substituted guanosine 3',5'-cyclic phosphate have been shown to activate adenylate cyclase in vitro.