Purines. LXII. Both enantiomers of N6-(1,3-dimethyl-2-butenyl)adenine and their 9-beta-D-ribofuranosides: synthesis and cytokinin activity.
Both enantiomers [(1'R)-6 and (1'S)-6] of N6-(1,3-dimethyl-2-butenyl)adenine and their 9-beta-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-beta-D-ribofuranoside (18) as well as 9-beta-D-ribofuranosyl-cis-zeatin (20) and 9-(2-deoxy-beta-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 approximately 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.
Fujii
T
T
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan.
Ohba
M
M
Kawamura
H
H
Nakashio
Y
Y
Honda
K
K
Matsubara
S
S
D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D001681:Biological Assay; D003583:Cytokinins / Q000494:pharmacology*; D007541:Isopentenyladenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D010947:Plants, Toxic; D013237:Stereoisomerism; D014026:Nicotiana / Q000187:drug effects
D003583:Cytokinins; C088989:N(6)-(1,3-dimethyl-2-butenyl)adenine; C088990:N-(1,3-dimethyl-2-butenyl)adenosine; D007541:Isopentenyladenosine; D000225:Adenine