Purines. LXII. Both Enantiomers of N^6-(1,3-Dimetyl-2-butenyl)adenine and Their 9-β-D-Ribofuranosides : Synthesis and Cytokinin Activity

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Both enantiomers [(1'R)-6 and (1'S)-6] of N6-(1,3-dimethyl-2- butenyl)adenine and their 9-β-D-ribofuranosides [(1''R)-16 and (1''S)-16] have been synthesized for the first time from both enantiomers of alanine (15) in nine steps. These aglycones and nucleosides, together with N6-(3- methyl-2-butenyl)adenine (5) and its 9-β-D-ribofuranoside (18) as well as 9- β-D-ribofuranosyl-cis-zeatin (20) and 9-(2-deoxy-β-D-ribofuranosyl)-cis- zeatin (19), were tested for cytokinin activity in the tobacco callus bioassay. The order of their activity was 5> (1'R)-6 > (1''R)-16≃18>(1'S)- 6>(1''S)-16>20>19. The bioassay results are compared with those obtained previously for the derivatives modified analogously in the N6-substituent in the cis- and trans-zeatin series.
公益社団法人日本薬学会の論文
1994-05-15