[A facile synthesis of adenosine 3', 5'-cyclic methylphosphonate and methylphosphonothioate].
A facile synthesis of adenosine 3', 5'-cyclic methylphosphonate (1) and 3', 5'-cyclic methylphosphonothioate (2) was accomplished by treatment of 2'-protected adenosine with O,O-bis (1-benzotriazolyl) methylphosphonate or O,O-bis (1-benzotriazolyl) methylphosphonothioate under mild conditions, respectively. The ability of the compounds to inhibit DNA synthesis in mice hepatoma was tested. A pair of diasteromers of 2'-protected (1) was separated and the configuration at the phosphorus atom was identified.
Wang
C G
CG
Dai
Y P
YP
Zhang
L H
LH
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002286:Carcinoma, Ehrlich Tumor / Q000473:pathology; D055598:Chemical Phenomena; D002621:Chemistry; D000242:Cyclic AMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004273:DNA, Neoplasm / Q000096:biosynthesis; D051379:Mice; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D004273:DNA, Neoplasm; D009946:Organothiophosphorus Compounds; C062913:adenosine 3',5'-cyclic methylphosphonate; C062914:adenosine 3',5'-cyclic methylphosphonothioate; D000242:Cyclic AMP