POLYMETHYLENE DERIVATIVES OF NUCLEIC BASES
171
9
9
N -(w-Hydroxycarbonyl-n-hexyl)adenine (Ie), R
N -(w-Hydroxy-n-amyl)hypoxanthine (IIc), R
f
f
1
1
0
1
7
.39 (3); H NMR (DMSO-d ): 1.30 (4 H, m, H3'–H4'), 0.40 (3); H NMR (DMSO-d , 50°C): 1.22 (2 H, m,
6
6
.52 (2 H, m, H5'), 1.90 (2 H, m, H2'), 2.15 (2 H, t, J5', 6' H3'), 1.40 (2 H, m, H4'), 1.75 (2 H, m, H2'), 3.40 (2 H,
.30, H6'), 4.20 (2 H, t, J1', 2' 7.30, H1'), 6.85 (2 H, s, t, J4', 5' 6.55, H5'), 4.00 (1 H, s, OH), 4.20 (2 H, t, J1', 2'
NH ), 8.08 (1 H, s, H2 or H8), and 8.15 (1 H, s, H8 or 7.15, H1'), 7.85 (1 H, s, H2), 8.05 (1 H, s, H8), and
2
+
+
1
2.00 (1 H, s, NH); MS: m/z 223 [M ], calc. 222
H2); MS: m/z 264 [M ], calc. 263 (ë ç N O ).
12
17
5
2
(
ë ç N O ).
10
14
4
2
9
N -(w-Hydroxycarbonyl-n-octyl)adenine (Ih), R
f
9
1
N -(w-Hydroxy-n-heptyl)hypoxanthine (IIf), R
.25 (2); H NMR (DMSO-d , 50°C): 1.26 (6 H, m,
0
.54 (3); H NMR (DMSO-d , 50°C): 1.22 (8 H, m,
f
6
1
0
H3'–H6'), 1.45 (2 H, m, H7'), 1.80 (2 H, m, H2'), 2.18
6
(
2 H, t, J7', 8' 7.20, H8'), 4.12 (2 H, t, J1', 2' 7.30, H1'), H3'–H5'), 1.38 (2 H, m, H6'), 1.78 (2 H, m, H2'), 3.40
(
2 H, t, J6', 7' 6.55, H7'), 4.00 (1 H, s, OH), 4.17 (2 H, t,
6
.80 (2 H, s, NH ), 8.08 (1 H, s, H8 or H2), and 8.12
2
+
J1', 2' 7.15, H1'), 7.85 (1 H, s, H2), 8.05 (1 H, s, H8), and
12.00 (1 H, s, NH); MS: m/z 251 [M ], calc. 250
(
(
1 H, s, H2 or H8); MS: m/z 292 [M ], calc. 291
+
(
ë ç N O ).
1
4
21
5
2
ë ç N O ).
12 18 4 2
9
N -(d-Hydroxycarbonyl-n-butyl)hypoxanthine
9
1
N -(w-Hydroxy-n-nonyl)hypoxanthine (IIi), R
(
IIb), R 0.22 (4); H NMR (DMSO-d ): 1.65 (2 H, m,
f
f
6
1
H3'), 1.95 (2 H, m, H2'), 2.15 (2 H, t, J3', 4' 7.20, H4'), 0.32 (2); H NMR (DMSO-d
, 50°C): 1.20 (10 H, m,
6
4
.15 (2 H, t, J1', 2' 7.20, H1'), 8.05 (1 H, s, H2), and 8.45 H3'–H7'), 1.40 (2 H, m, H8'), 1.80 (2 H, m, H2'), 3.40
+
(2 H, t, J8', 9' 6.55, H9'), 3.95 (1 H, s, OH), 4.20 (2 H, t,
(1 H, s, H8); MS: m/z 237 [M ], calc. 236
(ë ç N O ).
J1', 2' 7.15, H1'), 7.85 (1 H, s, H2), 8.00 (1 H, s, H8), and
1
0
12
4
3
+
1
2.05 (1 H, s, NH); MS: m/z 279 [M ], calc. 278
9
N -(w-Hydroxycarbonyl-n-hexyl)hypoxanthine
(
ë ç N O ).
14 22 4 2
1
(IIe), R 0.56 (3); H NMR (DMSO-d ): 1.25 (4 H, m,
f
6
H3'–H4'), 1.50 (2 H, m, H5'), 1.88 (2 H, m, H2'), 2.18
(
8
2 H, t, J5', 6' 7.15, H6'), 4.20 (2 H, t, J1', 2' 7.15, H1'),
ACKNOWLEDGMENTS
This work was partially supported by the Russian
.05 (1 H, s, H2), and 8.60 (1 H, s, H8); MS: m/z 265
+
[M ], calc. 264 (ë ç N O ).
12 16 4 3
Foundation for Basic Research (project no. 97-04-
9
N -(w-Hydroxycarbonyl-n-octyl)hypoxanthine (IIh), 49915), INTAS-RFBR (project no. 95-IN-RU-1214),
1
R 0.58 (3); H NMR (DMSO-d ): 1.25 (8 H, m, H3'– and PICS-RFBR (project no. 571).
f
6
H6'), 1.45 (2 H, m, H7'), 1.85 (2 H, m, H2'), 2.15 (2 H,
t, J7', 8' 7.15, H8'), 4.20 (2 H, t, J1', 2' 7.15, H1'), 8.05 (1
+
REFERENCES
H, s, H2), and 8.60 (1 H, s, H8); MS: m/z 293 [M ],
calc. 292 (ë ç N O ).
1
4
20
4
3
1. Makinskii, A.A., Kritsyn, A.M., Ul’yanova, E.A.,
Zakharova, O.D., and Nevinskii, G.A., Bioorg. Khim.,
9
N -(w-Hydroxy-n-amyl)adenine (Ic), R 0.18 (2);
f
2
000, vol. 26, pp. 735–742.
1
H NMR (DMSO-d ): 1.25 (2 H, m, H3'), 1.45 (2 H, m,
6
2
3
4
. Nesmeyanov, A.N. and Zakharkin, L.I., Izv. Akad. Nauk
SSSR, 1955, vol. 224, pp. 276–286.
H4'), 1.80 (2 H, m, H2'), 3.40 (2 H, t, J4', 5' 6.55, H5'),
.00 (1 H, s, OH), 4.13 (2 H, t, J1', 2' 7.15, H1'), 6.80
4
. Perbost, M., Lucas, M., Chavis, C., and Imbach, J.-L.,
Nucleosides Nucleotides, 1992, vol. 11, pp. 1489–1505.
(
2 H, s, NH ), 8.10 (1 H, s, H2 or H8), and 8.15 (1 H, s,
2
+
H8 or H2); MS: m/z 222 [M ], calc. 221 (ë ç N O).
1
0
15
5
. Meszarosova, K., Holy, A., and Masojidkova, M., Col-
lect. Czech. Chem. Commun., 2000, vol. 65, pp. 1109–
1125.
9
N -(w-Hydroxy-n-heptyl)adenine (If), R 0.38 (2);
f
1
H NMR (DMSO-d , 50°C): 1.28 (6 H, m, H3'–H5'),
6
1
.38 (2 H, m, H6'), 1.62 (2 H, m, H2'), 3.37 (2 H, t, J6', 7'
5. Tarrago-Litvak, L., Andreola, M.L., Nevinsky, G.A.,
Sarish-Cottin, L., and Litvak, S., FASEB J., 1994, vol. 8,
pp. 497–503.
6
.55, H7'), 4.00 (1 H, s, OH), 4.12 (2 H, t, J1', 2' 7.15,
H1'), 6.77 (2 H, s, NH ), 8.08 (1 H, s, H2 or H8), and
2
+
6. Pommier, Y., Biochimie, 1998, vol. 80, pp. 255–270.
8
.15 (1 H, s, H8 or H2); MS: m/z 250 [M ], calc. 249
(
ë ç N O).
12 19 5
7. Potmesil, M. and Kohn, K.W., DNA, Topoisomerases in
Cancer, New York: Oxford Univ. Press, 1991.
9
N -(w-Hydroxy-n-nonyl)adenine (Ii), R 0.40 (2);
f
1
8. Andoh, T., Ishii, K., Suzuki, Y., Takemoto, H., and
Okada, K., Proc. Natl. Acad. Sci. USA, 1987, vol. 84,
pp. 5565–5569.
H NMR (DMSO-d ): 1.25 (10 H, m, H3'–H7'), 1.48
6
(2 H, m, H8'), 1.80 (2 H, m, H2'), 3.37 (2 H, t, J8', 9' 6.55,
H9'), 3.98 (1 H, s, OH), 4.13 (2 H, t, J1', 2' 7.15, H1'),
9
. Andreola, M.-L., Nevinsky, G.A., Barr, Ph.J., Sarish-Cot-
tin, L., Bordier, B., Fournier, M., Litvak, S., and Tarrago-
Litvak, L., J. Biol. Chem., 1992, vol. 267, pp. 19356–
19362.
6
.80 (2 H, s, NH ), 8.08 (1 H, s, H2 or H8), and 8.15
2
+
(
1 H, s, H8 or H2); MS: m/z 278 [M ], calc. 277
(
ë ç N O).
1
4
23
5
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 27 No. 3 2001