Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Entry | R2 | R6 | R | Reagents and Conditions | Ratio 2:3:1 a | Yield (%) 2 b | Yield (%) 3 b |
---|---|---|---|---|---|---|---|
1 | Cl | NH2 | CH2-c-hexyl | RBr, K2CO3, DMF, rt, 72 h | 80:20:0 | 67, 2a | 10, 3a |
2 | Cl | NH2 | CH2-c-hexyl | ROH, DIAD, PPh3, THF, 70 °C, 14 h | 93:7:0 | 76, 2a | 5, 3a |
3 | OCONPh2 | NHAc | CH2-c-hexyl | RBr, K2CO3, DMF, rt, 72 h | 81:19:0 | 45, 2e | 7, 3e |
4 | OCONPh2 | NHAc | CH2-c-hexyl | ROH, DIAD, PPh3, THF, 70 °C, 14 h | 82:18:0 | 70, 2e | 3, 3e |
5 | Cl | NH2 | c-hexyl | RI, K2CO3, DMF, rt, 72 h | 15:0:85 | – c | – |
6 | Cl | NH2 | c-hexyl | ROTs, K2CO3, DMF, rt, 72 h | – d | 33, 2b | – c |
7 | Cl | NH2 | c-hexyl | ROH, DIAD, PPh3, THF, 70 °C, 14 h | 8:4:88 | – c | – c |
8 | Cl | NH2 | c-hexyl | ROH, DIAD, PPh3, THF, ultrasound, 14 h | 27:0:73 | 20, 2b | – |
9 | Cl | NH2 | c-hexyl | ROH, DIAD, PPh3, DMF, 150 °C, μW, 2 h | 41:8:51 | – c | – c |
10 | OCONPh2 | NHAc | c-hexyl | ROTs, K2CO3, THF, rt, 72 h | – d | 30, 2f | – c |
11 | OCONPh2 | NHAc | c-hexyl | ROTs, K2CO3, DMF, 80 °C, 72 h | – d,e | – c | – c |
12 | OCONPh2 | NHAc | c-hexyl | ROH, DIAD, PPh3, THF, 70 °C, 14 h | – d | 22, 2f | – c |
13 | Cl | NH2 | c-pentyl | RBr, K2CO3, DMF, rt, 72 h | 86:14:0 | 71, 2c | 5, 3c |
14 | Cl | NH2 | c-pentyl | ROH, DIAD, PPh3, THF, 70 °C, 14 h | 91:9:0 | 72, 2c | 6, 3c |
15 | OCONPh2 | NHAc | c-pentyl | RBr, K2CO3, DMF, rt, 72 h | 76:15:09 | 52, 2g | – c |
16 | OCONPh2 | NHAc | c-pentyl | ROH, DIAD, PPh3, THF, 70 °C, 14 h | 90:10:0 | 58, 2g | – c |
17 | Cl | NH2 | c-pent-2-enyl | RBr, K2CO3, DMF, rt, 24 h | 23:16:61 | 18, 2d | – c |
18 | Cl | NH2 | c-pent-2-enyl | ROH, DIAD, PPh3, THF, 70 °C, 42 h | 55:18:27 | 40, 2d | – c |
19 | Cl | NH2 | c-pent-2-enyl | ROAc, Pd(PPh3)4,NaH, DMSO, f 50 °C, 48 h | 75:25:0 | 53, 2d | 18, 3d |
Entry | Starting Material a | Reagents and Conditions | Yield (%) 4 a,b |
---|---|---|---|
1 | 2a | Br2, H2O | 79%, 4a |
2 | 10 | RBr, K2CO3, DMF | 34%, 4a |
3 | 10 | ROH, DIAD, PPh3, THF, 70 °C | 56%, 4a |
4 | 2b | Br2, H2O | 70%, 4b |
5 | 2c | Br2, H2O | 81%, 4c |
6 | 2d | 1. LDA, 2. CCl2BrCCl2Br, THF, −78 °C | 32%, 4d |
7 | 10 | ROH, DEAD, PPh3, THF, 70 °C | 42%, 4d |
8 | 10 | ROAc, Pd(PPh3)4, NaH, DMF, 50 °C | 29%, 4d |
2.2. Biology
Compound | X | R | % Activity |
---|---|---|---|
5a | OH a | CH2-c-hexyl | 89 ± 5 |
5b | OH a | c-hexyl | 92 ± 2 |
6b | Cl | c-hexyl | 70 ± 11 |
5c | OH | c-pentyl | 101 ± 12 |
6c | Cl | c-pentyl | 72 ± 9 |
5d | OH | c-pent-2-enyl | 92 ± 7 |
6d | Cl | c-pent-2-enyl | 84 ± 3 |
Compound | X | R | % Activity |
---|---|---|---|
5a | OH a | CH2-c-hexyl | 96 ± 3 |
5b | OH a | c-hexyl | 123 ± 20 |
6b | Cl | c-hexyl | 73 ± 37 |
5c | OH | c-pentyl | 102 ± 16 |
6c | Cl | c-pentyl | 108 ± 18 |
5d | OH | c-pent-2-enyl | 104 ± 21 |
6d | Cl | c-pent-2-enyl | 89 ± 13 |
3. Experimental Section
3.1. General Information
3.2. Synthesis
3.2.1. 2-Amino-6-chloro-9-(cyclohexylmethyl)-9H-purine (2a) and 2-Amino-6-chloro-7-(cyclohexylmethyl)-7H-purine (3a)
3.2.2. 2-Amino-6-chloro-9-(cyclohexyl)-9H-purine (2b)
3.2.3. 2-Amino-6-chloro-9-(cyclopentyl)-9H-purine (2c) and 2-Amino-6-chloro-7-(cyclopentyl)-7H-purine (3c)
3.2.4. 2-Amino-6-chloro-9-(cyclopent-2-enyl)-9H-purine (2d) and 2-Amino-6-chloro-7-(cyclopent-2-enyl)-7H-purine (3d)
3.2.5. 2-Acetamido-9-(cyclohexylmethyl)-9H-purin-6-yl diphenylcarbamate (2e) and 2-Acetamido-7-(cyclohexylmethyl)-7H-purin-6-yl diphenylcarbamate (3e)
3.2.6. 2-Acetamido-9-(cyclohexyl)-9H-purin-6-yl diphenylcarbamate (2f)
3.2.7. 2-Acetamido-9-(cyclopentyl)-9H-purin-6-yl diphenylcarbamate (2g)
3.2.8. 2-Amino-8-bromo-6-chloro-9-(cyclohexylmethyl)-9H-purine (4a)
3.2.9. 2-Amino-8-bromo-6-chloro-9-(cyclohexyl)-9H-purine (4b)
3.2.10. 2-Amino-8-bromo-6-chloro-9-(cyclopentyl)-9H-purine (4c)
3.2.11. 2-Amino-8-bromo-6-chloro-9-(cyclopent-2-enyl)-9H-purine (4d)
3.2.12. 9-(Cyclohexylmethyl)-8-oxoguanine (5a)
3.2.13. 9-(Cyclohexyl)-8-oxoguanine (5b) and 2-Amino-6-chloro-9-cyclohexyl-7H-purin-8(9H)-one (6b)
3.2.14. 9-(Cyclopentyl)-8-oxoguanine (5c) and 2-Amino-6-chloro-9-cyclopentyl-7H-purin-8(9H)-one (6c)
3.2.15. 9-(Cyclopent-2-enyl)-8-oxoguanine (5d) and 2-Amino-6-chloro-9-(cyclopent-2-enyl)-7H-purin-8(9H)-one (6d)
3.2.16. N-[9-(Cyclohexylmethyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]acetamide (7)
3.2.17. 8-Bromo-6-chloro-N,9-bis(tetrahydro-2H-pyran-2-yl)-9H-purin-2-amine (9)
3.2.18. 2-Amino-8-bromo-6-chloro-1H-purine (10)
3.3. DNA Glycosylase Activity Assay
4. Conclusions
Supplementary Material
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Mahajan, T.R.; Ytre-Arne, M.E.; Strøm-Andersen, P.; Dalhus, B.; Gundersen, L.-L. Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1. Molecules 2015, 20, 15944-15965. https://doi.org/10.3390/molecules200915944
Mahajan TR, Ytre-Arne ME, Strøm-Andersen P, Dalhus B, Gundersen L-L. Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1. Molecules. 2015; 20(9):15944-15965. https://doi.org/10.3390/molecules200915944
Chicago/Turabian StyleMahajan, Tushar R., Mari Eknes Ytre-Arne, Pernille Strøm-Andersen, Bjørn Dalhus, and Lise-Lotte Gundersen. 2015. "Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1" Molecules 20, no. 9: 15944-15965. https://doi.org/10.3390/molecules200915944