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Hong et al.
Arch. Pharm. Chem. Life Sci. 2005, 338, 522−527
(1-Hydroxymethyl-cyclopent-3-enyl)-methanol 21
1-[1-(tert-Butyl-dimethyl-silanyloxymethyl)cyclopent-3-enylmethyl]-
cytosine 27
Compound 21 was synthesized from compound 20 using a similar
procedure described for synthesizing compound 7: yield 82%; 1H
NMR (CDCl3, 300 MHz) δ 5.64 (s, 2H), 3.67 (s, 4H), 2.20 (4H);
13C NMR (CDCl3) δ 128.74, 69.83, 47.54, 38.63; Anal. calcd. for
C7H12O2: C, 65.60; H, 9.44. Found: C, 65.38; H, 9.30.
Compound 27 was synthesized from compound 23 using the
method described for synthesizing compound 10: yield 48%; 1H
NMR (CDCl3, 300 MHz) δ 8.02 (d, J ϭ 5.7 Hz, 1H), 6.10 (d, J ϭ
5.7 Hz, 1H), 5.61 (s, 2H), 5.11 (s, 2H), 4.3 (s, 2H), 3.62 (s, 2H), 2.29
(s, 4H), 0.86 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3) δ 165.61,
164.65, 157.32, 128.85, 99.19, 69.76, 65.81, 47.10, 38.68, 25.80,
18.16, Ϫ5.57; Anal. calcd. for C17H29N3O2Si: C, 60.86; H, 8.71; N,
12.52. Found: C, 60.99; H, 8.84; N, 12.40.
[1-(tert-Butyl-dimethyl-silanyloxymethyl)cyclopent-3-enyl]-
methanol 22
Compound 22 was synthesized from compound 21 using the
method described for synthesizing compound 8: yield 95%; 1H
NMR (CDCl3, 300 MHz) δ 5.53 (s, 2H), 3.57 (d, J ϭ 5.7 Hz, 4H),
2.20Ϫ2.01 (m, 4H), 0.83 (s, 9H), 0.03 (s, 6H); 13C NMR (CDCl3) δ
128.74, 47.51, 38.51, 25.63, 18.06, Ϫ5.70; Anal. calcd. for
C13H26O2Si: C, 64.41; H, 10.81. Found: C, 64.22; H, 10.91.
9-[1-(Hydroxymethyl)cyclopent-3-enylmethyl]adenine 28
Compound 28 was synthesized from compound 24 using a similar
procedure described for synthesizing compound 14: yield 72%; mp.
184Ϫ186°C; UV (H2O) λmax 261.0 nm; 1H NMR (DMSO-d6, 300
MHz) δ 8.13 (s, 1H), 8.09 (s, 1H), 7.24 (br s, 2H), 5.54 (s, 2H), 5.26
(t, J ϭ 5.7 Hz, 1H), 4.08 (s, 2H), 3.17 (d, J ϭ 5.1 Hz, 2H), 2.34 (d,
J ϭ 15.0 Hz, 2H), 2.09 (d, J ϭ 15.0 Hz, 2H); 13C NMR (DMSO-
d6) δ 156.03, 152.35, 150.08, 141.67, 128.72, 118.22, 64.86, 48.14,
47.63, 39.08; Anal. calcd. for C12H15N5O: C, 58.76; H, 6.16; N,
28.55. Found: C, 58.58; H, 6.01; N, 28.38.
Methanesulfonic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-
cyclopent-3-enylmethyl ester 23
Compound 23 was synthesized from compound 22 using a similar
procedure described for synthesizing compound 9: yield 82%; 1H
NMR (CDCl3, 300 MHz) δ 5.54 (s, 2H), 4.12 (s, 2H), 3.45 (s, 2H),
2.94 (s, 3H), 2.15 (s, 4H), 0.84 (s, 9H), 0.02 (s, 6H); 13C NMR
(CDCl3) δ 128.52, 72.52, 65.26, 47.09, 38.39, 36.75, 25.76, 18.15,
Ϫ5.58; Anal. calcd. for C14H28O4SSi: C, 52.46; H, 8.81. Found: C,
52.65; H, 8.72.
1-[1-(Hydroxymethyl)cyclopent-3-enylmethyl]uracil 29
Compound 29 was synthesized from compound 25 using the
method described for synthesizing compound 14: yield 63%; mp.
169-171°C; UV (H2O) λmax 261.0 nm; 1H NMR (DMSO-d6, 300
MHz) δ 11.21 (br s, 1H), 7.57 (d, J ϭ 5.7 Hz, 1H), 5.67 (s, 2H),
5.51 (d, J ϭ 5.7 Hz, 1H), 4.86 (t, J ϭ 5.6 Hz, 1H), 4.09 (s, 2H),
3.62 (s, 2H), 2.38 (s, 4H); 13C NMR (DMSO-d6) δ 163.54, 152.21,
146.87, 128.51, 101.21, 65.33, 49.91, 47.62, 38.31; Anal. calcd. for
C11H14N2O3: C, 59.45; H, 6.35; N, 12.61. Found: C, 59.20; H, 6.19;
N, 12.88.
9-[1-(tert-Butyl-dimethyl-silanyloxymethyl)cyclopent-3-enylmethyl]-
adenine 24
Compound 24 was synthesized from the methylate 23 using a simi-
lar procedure described for synthesizing 10: yield 52%; 1H NMR
(CDCl3, 300 MHz) δ 8.25 (s, 1H), 7.82 (s, 1H),5.83 (s, 2H), 5.51 (s,
2H), 4.21 (s, 2H), 3.30 (s, 2H), 2.34 (d, J ϭ 14.7 Hz, 2H), 2.00 (d,
J ϭ 14.7 Hz, 2H), 0.85 (s, 9H), 0.02 (s, 6H); 13C NMR (CDCl3) δ
155.44, 152.89, 150.81, 141.91, 128.72, 119.16, 66.20, 48.69, 47.79,
39.71, 25.87, 18.21, Ϫ5.44; Anal. calcd. for C18H29N5OSi: C, 60.13;
H, 8.13; N, 19.48. Found: C, 60.31; H, 8.26; N, 19.50.
1-[1-(Hydroxymethyl)cyclopent-3-enylmethyl]thymine 30
Compound 30 was prepared from compound 26 using the pro-
cedure described for synthesizing compound 14: yield 79%; mp.
168-170°C; UV (H2O) λmax 267.1 nm; 1H NMR (DMSO-d6, 300
MHz) δ 11.21 (br s, 1H), 7.40 (s, 1H), 5.77 (s, 2H), 4.95 (t, J ϭ 5.7
Hz, 1H), 4.01 (s, 2H), 3.53 (s, 2H), 2.34 (s, 4H), 1.70 (s, 3H); 13C
NMR (DMSO-d6) δ 164.38, 152.11, 143.09, 128.61, 107.15, 70.02,
66.71, 47.87, 39.21, 12.02; Anal. calcd. for C12H16N2O3: C, 61.00;
H, 6.83; N, 11.86. Found: C, 60.88; H, 6.75; N, 12.01.
1-[1-(tert-Butyl-dimethyl-silanyloxymethyl)cyclopent-3-enylmethyl]-
uracil 25
Compound 25 was prepared from compound 23 using the method
described for synthesizing compound 10: yield 40%; 1H NMR
(CDCl3, 300 MHz) δ 8.87 (br s, 1H), 7.42 (d, J ϭ 7.6 Hz, 1H), 6.67
(s, 2H), 5.50 (d, J ϭ 7.6 Hz, 1H), 4.19 (s, 2H), 3.61 (s, 2H), 2.31 (s,
4H), 0.87 (s, 9H), 0.02 (s, 6H); 13C NMR (CDCl3) δ 163.66, 151.81,
147.94, 128.71, 100.65, 68.78, 66.31, 48.91, 38.38, 25.67, 18.28,
Ϫ5.40; Anal. calcd. for C17H28N2O3Si: C, 60.68; H, 8.39; N, 8.32.
Found: C, 60.89; H, 8.41; N, 8.20.
1-[1-(Hydroxymethyl)cyclopent-3-enylmethyl]cytosine 31
Compound 31 was synthesized from compound 27 using the
method described for synthesizing compound 14: yield 77%; mp.
162Ϫ164°C; UV (H2O) λmax 271.0 nm; 1H NMR (DMSO-d6, 300
MHz) δ 7.80 (d, J ϭ 5.4 Hz, 1H), 7.06 (br d, 2H), 5.75 (d, J ϭ 5.4
Hz, 1H), 5.55 (s, 2H), 4.89 (t, J ϭ 5.5 Hz, 1H), 4.14 (s, 2H), 3.52
(s, 4H), 3.32 (s, 2H), 2.23 (s, 4H); 13C NMR (DMSO-d6) δ 165.54,
158.21, 146.67, 128.81, 98.21, 67.12, 65.32, 46.01, 39.12; Anal.
calcd. for C11H15N3O2: C, 59.71; H, 6.83; N, 18.99. Found: C, 59.48;
H, 6.73; N, 18.90.
1-[1-(tert-Butyl-dimethyl-silanyloxymethyl-cyclopent-3-enylmethyl]-
thymine 26
Compound 26 was synthesized from compound 23 using the
method described for synthesizing compound 10: yield 41%; 1H
NMR (CDCl3, 300 MHz) δ 8.38 (br s, 1H), 7.34 (s, 1H), 5.60 (s,
2H), 4.21 (s, 2H), 3.55 (s, 2H), 2.22 (s, 4H), 1.76 (s, 3H), 0.85 (s,
9H), 0.03 (s, 6H); 13C NMR (CDCl3) δ 164.12, 152.03, 142.45,
128.51, 102.81, 67.85, 65.65, 47.66, 38.89, 25.67, 18.72, 12.21,
Ϫ5.53; Anal. calcd. for C18H30N2O3Si: C, 61.68; H, 8.63; N, 7.99.
Found: C, 61.78; H, 8.77; N, 8.09.
Evaluation of anti-HIV activity and cytotoxicity
The anti-HIV activity and cytotoxicity were determined as de-
scribed elsewhere [13].
2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim