title: Alkylated cAMP derivatives: selective synthesis and biological activities.
abstract: Many alkylated cAMPs have been prepared and tested for their antitumor and cardiac activities. Treatment of cAMP with several bases and alkyl bromides gave alkyltriesters of cAMP (2), N6,N6,2'-O-trialkyl cAMPs (3), N6,2'-O-dialkyl cAMPs (4) and 2'-O-monoalkyl cAMPs (5) in one step. N6,N6-dialkyl cAMPs (6) were prepared from 2'-O-tosyl cAMP by the similar alkylation, followed by detosylation. Synthesis of N6-monoalkyl cAMPs (7) was achieved by the reductive alkylation of cAMP with aldehydes in one step. Alkyl triesters of cAMP exhibited antitumor activities against P815 cells. N6-mono and N6,N6-dialkyl cAMPs showed significant cardiac activities.
authors.affiliation: Research and Development Division, Kikkoman Corporation, Chiba, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Kataoka
authors.forename: J
authors.initials: J
authors.lastname: Imai
authors.forename: N
authors.initials: N
authors.lastname: Yamaji
authors.forename: M
authors.initials: M
authors.lastname: Kato
authors.forename: M
authors.initials: M
authors.lastname: Saito
authors.forename: T
authors.initials: T
authors.lastname: Kawada
authors.forename: S
authors.initials: S
authors.lastname: Imai
mesh_terms: D000478:Alkylation; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002316:Cardiotonic Agents / Q000138:chemical synthesis; D000242:Cyclic AMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006168:Guinea Pigs; D066298:In Vitro Techniques; D051379:Mice
chemical_list: D000970:Antineoplastic Agents; D002316:Cardiotonic Agents; D000242:Cyclic AMP