T. Anderson, C. Frihart, N. Leonard
Aug 1, 1975
Citations
0
Influential Citations
33
Citations
Journal
Phytochemistry
Abstract
Abstract Using the tobacco bioassay a comparison was made between the cytokinin activities of the following series of compounds with different connecting links (6-NH, S, O, CH2) between the purine ring and isopentenyl or benzyl groups: 6-(3-methyl-2-butenylamino)purine (1a), 6-(3-methyl-2- butenylthio)purine (1b), 6-(3-methyl-2-butenyloxy)purine (1c), and 6-(4-methyl-3-pentenyl)purine (1d); 6-benzylaminopurine (2a), 6-benzylthiopurine (2b), 6-benzyloxypurine (2c), and 6-(2-phenethyl)purine (2d); also 6-trans-styrylpurine (3), the synthetic precursor of 2d. All possess cytokinin activity, thus providing evidence that the intact base, consisting of nucleus and sidechain at the purine 6-position, is necessary and sufficient for such activity as measured in the tobacco bioassay. The biological activity in the 6-(3-methyl- 2-butenyl-X)purine series decreases as a function of the linkage group in the order X = NH > CH2 > S ⪢ O and in the 6-benzyl-X-purine series in the order X = NH > CH2 = O ⪢ S. The 6-trans-styrylpurine (3) is about equally active as 6-(2-phenethyl)purine (2d).