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.
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