The Synthesis, Mutagenic and Pharmacological Activities of 2-Carbon-Substituted Adenosines

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Abstract
2′-Deoxy-2-(p-nitrophenyl)-adenosine (.15) was found to be the most potent mutagen when tested with S. typhimurium TA 98 and TA 100 in the series of compounds, whose activity towards TA 98 is one order of magnitude greater than that of 4-nitroquinoline N-oxide. In another series of reactions, synthesis of 2-alkynyl-adenosines (18) was achieved through the palladium catalyzed cross-coupling of terminal alkynes with 2-iodoadenosine (17). Compounds bearing the 2-C[dbnd]CCH(R)OH side-chain exhibited potent antiallergic activity in rats. These compounds, however, possessed hypotensive activity accompanied by a decrease in heart rate whereas with a longer alkyl side-chain at the 2-position, compounds showed selective hypotensive activity.