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. 2020 May 29;10(6):832. doi: 10.3390/biom10060832

Table 1.

Summary of substitutions at N9, N6, C2, and C8 atoms, and their combinations, that resulted in compounds with significantly higher activity than appropriate standards in indicated CK bioassays.

Bioassay Std. Position of the Substituent on the Purine Ring Ref.
N9 N6 C2 C8
Amaranthus caudatus betacyanin BAP β-D-ribofuranosyl- 2-chlorobenzyl-, 3-chlorobenzyl-,
2-bromobenzyl-, 3-bromobenzyl-,
3-iodobenzyl-, 3,5-difluorobenzyl-,
2,4,5-trifluorobenzyl-, 2-chloro-4-fluorobenzyl-,
2-trifluoromethylbenzyl-,
3-trifluoromethoxybenzyl-
H H [45]
2-fluorobenzyl-, 3-fluorobenzyl-,
4-fluorobenzyl-, 2-chlorobenzyl-,
3-chlorobenzyl-, 2-bromobenzyl-,
3-bromobenzyl-, 4-bromobenzyl-, 3-iodobenzyl-
Cl H [46]
2′-deoxy-β-D-ribofuranosyl- 3-hydroxybenzyl-, 2-fluorobenzyl-, 4-fluorobenzyl-,
2-chlorobenzyl, 3-chlorobenzyl-,
2-bromobenzyl-,
3-brombenzyl-, 2-methybenzyl-,
2-trifluoromethylbenzyl-
H H [120]
tetrahydropyran-2-yl isopentenyl-, furfuryl- H 3-aminopropyl-,
4-aminobutyl-,
methylsulfanyl-,
dimethyl-, allyl-
[172]
benzyl- H H [147]
tetrahydrofuran-2-yl benzyl-, 2-methoxybenzyl-, 3-methoxybenzyl- H H [147]
thiofen-2-yl- Cl H [176]
iP tetrahydropyran-2-yl, ethoxyethyl-, 2-bromoethyl-,
2-chloroethyl-, 4-ethoxy-4-oxobutyl-
isopentenyl- H H [158]
Senescence (WLS) BAP β-D-ribofuranosyl- 2-fluorobenzyl-, 3-fluorobenzyl-,
4-fluorobenzyl-, 2-chlorobenzyl-,
4-chlorobenzyl-, 2-methylbenzyl-,
3-methybenzyl-, 2-methoxybenzyl-,
3-methoxybenzyl-, 3,4-dichlorobenzyl-,
2,3-dimethoxybenzyl-, 2,4-difluorobenzyl-,
3,5-difluorobenzyl-, 2,3,4-trifluorobenzyl-,
2,3,6-trifluorobenzyl-, 2-chloro-4-fluorobenzyl-,
3-chloro-4-fluorobenzyl-, 2-hydroxy-5-methylbenzyl-,
2-difluoromethoxybenzyl-
H H [45]
2-fluorobenzyl-, 3-fluorobenzyl-, 4-fluorobenzyl-,
2-chlorobenzyl-, 3-chlorobenzyl-,4-chlorobenzyl-,
3-bromobenzyl-, 4-bromobenzyl-
Cl H [46]
β-D-arabinofuranosyl- benzyl-, 2-fluorobenzyl-, 3-fluorobenzyl-,
4-fluorobenzyl-, 3-chlorobenzyl-,
2-methoxybenzyl-,3-methoxybenzyl-,
3-hydroxybenzyl-, 3-methylbenzyl-,
2,5-difluorobenzyl-, 3,5-difluorobenzyl-
H H [134]
2′-deoxy-β-D-ribofuranosyl- benzyl-, 2-hydroxybenzyl-, 3-hydroxybenzyl-,
4-hydroxybenzyl, 3-methoxybenzyl-, furfuryl-
2,5-dimethoxybenzyl-, 2-fluorobenzyl-, 3-fluorobenzyl-,
4-fluorobenzyl-, 2-chlorobenzyl-, 3-chlorobenzyl-,
4-chlorobenzyl-, 2-bromobenzyl-, 3-bromobenzyl-,
4-bromobenzyl-, 2-methylbenzyl-, 3-methylbenzyl-,
2-trifluoromethylbenzyl-, 3-trifluoromethylbenzyl-,
H H [120]
tetrahydropyran-2-yl benzyl-, 3-hydroxybenzyl-,
2-methoxybenzyl-,
H H [147]
tetrahydrofuran-2-yl benzyl-, 3-hydroxybenzyl- H H [147]
tetrahydrofuran-2-yl-, thiofen-2-yl-,
5-methylthiofen-2-yl-
H H [176]
tetrahydrofurfuryl- Cl H [176]
Kin 2-bromoethyl-, 2-chloroethyl-,
4-chlorobutyl-, 1-ethoxyethyl-, tetrahydrofuran-2-yl
furfuryl- H H [157]
Tobaccocallus BAP β-D-ribofuranosyl- 2-fluorobenzyl-, 4-fluorobenzyl-,
2-bromobenzyl-, 2-methoxybenzyl-
H H [45]
2-flourobenzyl-, 3-fluorobenzyl-, 4-fluorobenzyl-,
2-chlorobenzyl-, 3-chlorobenzyl-, 4-bromobenzyl-
Cl H [46]
2′-deoxy-β-D-ribofuranosyl- benzyl-, 4-fluorobenzyl-, furfuryl- H H [120]
tetrahydropyran-2-yl isopentenyl-, furfuryl- H 2-aminoethyl-,
3-aminopropyl-,
4-aminobutyl-,
6-aminohexyl-,
methoxy-,
2-hydroxyethyl-
[172]
benzyl- H H [147]
tetrahydrofuran-2-yl furfuryl-, thiofen-2-yl, 5-hydroxymethylfuran-2-yl- H H [176]
furfuryl-, tetrahydrofurfuryl-, thiofen-2-yl- Cl H [176]
iP ethoxyethyl-, acetoxy-,
2-azidoethyl-, 4-chlorobutyl-,
3-cyanopropyl-
isopentenyl- H H [158]
Kin 2-bromoethyl, 2-chloroethyl-,
1-ethoxyethyl-, tetrahydrofuran-2-yl
furfuryl- H H [157]