title: Purines. LXII. Both enantiomers of N6-(1,3-dimethyl-2-butenyl)adenine and their 9-beta-D-ribofuranosides: synthesis and cytokinin activity.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kanazawa University, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Fujii
authors.forename: M
authors.initials: M
authors.lastname: Ohba
authors.forename: H
authors.initials: H
authors.lastname: Kawamura
authors.forename: Y
authors.initials: Y
authors.lastname: Nakashio
authors.forename: K
authors.initials: K
authors.lastname: Honda
authors.forename: S
authors.initials: S
authors.lastname: Matsubara
mesh_terms: 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
chemical_list: D003583:Cytokinins; C088989:N(6)-(1,3-dimethyl-2-butenyl)adenine; C088990:N-(1,3-dimethyl-2-butenyl)adenosine; D007541:Isopentenyladenosine; D000225:Adenine