[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.
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D000262:Adenylyl Cyclases / Q000378:metabolism; D000818:Animals; D006152:Cyclic GMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004273:DNA, Neoplasm / Q000096:biosynthesis; D008113:Liver Neoplasms / Q000473:pathology; D051379:Mice; D012516:Osteosarcoma / Q000473:pathology; D012334:RNA, Neoplasm / Q000096:biosynthesis; D051381:Rats
D004273:DNA, Neoplasm; D012334:RNA, Neoplasm; C062812:2'-dimethyl-tert-butylsilyl-N(2)-(N,N-dimethylamino)methylene-guanosine 3',5'-cyclic diethylphosphoramidate; C062811:n-butyl 2'-dimethyl-tert-butylsilyl-N(2)-(N,N-dimethylamino)methylene-guanosine 3,',5'-cyclic phosphate; D000262:Adenylyl Cyclases; D006152:Cyclic GMP