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ZHAO ET AL.
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(ddd, J = 13.5, 8.5, 4.9 Hz, 1H, CH2), 0.98 (t, J = 7.3 Hz, 3H, CH3). 13
C
J = 115.1 Hz, 1H, NH), 10.70 (d, J = 445.4 Hz, 1H, OH), 9.88 (d,
J = 47.0 Hz, 1H, OH), 8.24 (d, J = 39.7 Hz, 1H, N═CH), 7.48, 7.29 (dd,
J = 76.48 Hz, 9.1 Hz, 1H, Ph–H), 6.35–6.29 (m, 2H, Ph–H), 4.86 (dd,
J = 8.1, 3.9 Hz, 1H, OH), 4.62 (dd, J = 10.4, 4.1 Hz, 1H, OH), 4.54 (dd,
J = 6.2, 2.0 Hz, 1H, OH), 4.27 (p, J = 7.8 Hz, 1H, CH), 4.08–3.86 (m,
2H, CH2), 3.80 (dp, J = 8.2, 4.2 Hz, 1H, CH), 3.61 (d, J = 4.0 Hz, 2H,
2CH), 3.02 (ddt, J = 27.0, 13.4, 6.8 Hz, 2H, CH2), 2.43 (dq, J = 13.4,
8.2 Hz, 1H, CH2), 1.68 (h, J = 7.2 Hz, 2H, CH2), 1.25–1.19 (m, 1H,
CH2), 0.98 (t, J = 7.3 Hz, 3H, CH3). 13C NMR (101 MHz, DMSO‐d6) δ
169.72, 168.39, 164.83, 162.19, 161.09, 159.75, 158.01, 131.62,
110.88, 108.11, 104.85, 103.07, 77.37, 75.21, 74.00, 56.00, 37.44,
32.50, 31.33, 23.16, 13.73. HRMS (ESI) m/z: calcd. for C21H26N5O6S
[M+H]+ 476.1604; found, 476.1612.
NMR (101 MHz, DMSO‐d6) δ 170.72, 168.13, 162.24, 158.00,
143.37, 134.65, 130.26, 129.30, 127.24, 105.44, 77.35, 75.03,
73.96, 55.96, 37.41, 32.48, 31.45, 23.20, 13.75. HRMS (ESI) m/z:
calcd. for C21H26N5O4S [M+H]+ 444.1706; found, 444.1711.
4‐{2‐[(E)‐4‐Hydroxybenzylidene]hydrazinyl}‐2‐(propylthio)‐7‐
[(1R,2S,3R,4S)‐2,3,4‐trihydroxycyclopentyl]‐5,7‐dihydro‐6H‐
pyrrolo‐[2,3‐d]pyrimidin‐6‐one (19)
The title compound 19 (184 mg) was prepared from 10 (356 mg,
1 mmol) and 4‐hydroxybenzaldehyde (146 mg, 1.2 mmol) using the
procedure described for compound 11 in 40.1% yield as a white solid,
m.p. 158.8–159.9°C. 1H NMR (400 MHz, DMSO‐d6) δ 11.34 (d,
J = 13.6 Hz, 1H, NH), 9.89 (d, J = 6.9 Hz, 1H, OH), 8.02 (d, J = 71.5 Hz,
1H, N═CH), 7.53 (dd, J = 8.5, 6.6 Hz, 2H, Ph–H), 6.82 (dd, J = 8.7,
2.9 Hz, 2H, Ph–H), 4.86 (dd, J = 11.1, 4.0 Hz, 1H, OH), 4.72–4.44 (m,
2H, 2OH), 4.27 (p, J = 7.8 Hz, 1H, CH), 4.07–3.93, 3.63 (m, 3H, CH,
CH2), 3.80 (s, 1H, CH), 3.61 (s, 1H, CH), 3.00 (ddt, J = 27.8, 13.7,
6.9 Hz, 2H, CH2), 2.48–2.34 (m, 1H, CH2), 1.68 (h, J = 7.3 Hz, 2H,
CH2), 1.21 (dp, J = 13.5, 5.0, 4.5 Hz, 1H, CH2), 0.98 (t, J = 7.3 Hz, 3H,
CH3). 13C NMR (101 MHz, DMSO‐d6) δ 170.33, 168.08, 162.25,
159.60, 157.96, 143.76, 128.95, 125.69, 116.16, 105.62, 77.36,
75.08, 74.03, 55.98, 37.39, 32.50, 31.41, 23.19, 13.74. HRMS (ESI)
m/z: calcd. for C21H26N5O5S [M+H]+ 460.1655; found, 460.1643.
4‐{2‐[(E)‐4‐Methylbenzylidene]hydrazinyl}‐2‐(propylthio)‐7‐
[(1R,2S,3R,4S)‐2,3,4‐trihydroxycyclopentyl]‐5,7‐dihydro‐6H‐
pyrrolo‐[2,3‐d]pyrimidin‐6‐one (22)
The title compound 22 (256 mg) was prepared from 10 (356 mg,
1 mmol) and 4‐methylbenzaldehyde (144 mg, 1.2 mmol) using the pro-
cedure described for compound 11 in 56.9% yield as a white solid, m.p.
151.3–152.6°C. 1H NMR (400 MHz, DMSO‐d6) δ 11.49 (d, J = 15.7 Hz,
1H, NH), 8.08 (d, J = 71.9 Hz, 1H, N═CH), 7.59 (t, J = 7.5 Hz, 2H, Ph–H),
7.25 (d, J = 7.7 Hz, 2H, Ph–H), 4.87 (dd, J = 10.8, 4.0 Hz, 1H, OH), 4.63
(dd, J = 10.4, 4.1 Hz, 1H, OH), 4.54 (d, J = 5.9 Hz, 1H, OH), 4.27 (p,
J = 7.9 Hz, 1H, CH), 4.12–3.92, 3.62 (m, 3H, CH, CH2), 3.81–3.78 (m, 1H,
CH), 3.62–3.57 (m, 1H, CH), 3.02 (ddt, J = 27.5, 13.4, 6.8 Hz, 2H, CH2),
2.48–2.38 (m, 1H, CH2), 2.33 (s, 3H, CH3), 1.68 (h, J = 7.4 Hz, 2H, CH2),
1.25–1.17 (m, 1H, CH2), 0.98 (t, J = 7.3 Hz, 3H, CH3). 13C NMR
(101 MHz, DMSO‐d6) δ 170.59, 168.10, 162.24, 157.99, 143.47,
140.01, 131.95, 129.89, 127.23, 105.48, 77.35, 75.03, 73.97, 55.95,
37.41, 32.48, 31.44, 23.20, 21.49, 13.75. HRMS (ESI) m/z: calcd. for
4‐{2‐[(E)‐3‐Hydroxybenzylidene]hydrazinyl}‐2‐(propylthio)‐7‐
[(1R,2S,3R,4S)‐2,3,4‐trihydroxycyclopentyl]‐5,7‐dihydro‐6H‐
pyrrolo‐[2,3‐d]pyrimidin‐6‐one (20)
The title compound 20 (333 mg) was prepared from 10 (356 mg,
1 mmol) and 3‐hydroxybenzaldehyde (146 mg, 1.2 mmol) using the
procedure described for compound 11 in 72.4% yield as a yellow
solid, m.p. 126.6–128.4°C. 1H NMR (400 MHz, DMSO‐d6) δ 11.50
(d, J = 17.1 Hz, 1H, NH), 9.60 (d, J = 2.7 Hz, 1H, OH), 8.04 (d,
J = 70.8 Hz, 1H, N═CH), 7.24 (td, J = 7.8, 2.5 Hz, 1H, Ph–H), 7.17 (q,
J = 2.2 Hz, 1H, Ph–H), 7.09 (d, J = 7.7 Hz, 1H, Ph–H), 6.82 (dd, J = 8.1,
2.4 Hz, 1H, Ph–H), 4.86 (dd, J = 9.1, 3.9 Hz, 1H, OH), 4.63 (dd, J = 9.0,
4.2 Hz, 1H, OH), 4.54 (dd, J = 6.2, 2.9 Hz, 1H, OH), 4.28 (p, J = 7.8 Hz, 1H,
CH), 4.11–3.93, 3.63 (m, 3H, CH, CH2), 3.81 (tq, J = 7.3, 4.1 Hz, 1H, CH),
3.62 (d, J = 5.5 Hz, 1H, CH), 3.00 (ddt, J = 27.8, 13.7, 6.9 Hz, 2H, CH2),
2.43 (ddd, J = 13.5, 8.7, 6.9 Hz, 1H, CH2), 1.68 (h, J = 7.2 Hz, 2H, CH2),
1.25–1.18 (m, 1H, CH2), 0.98 (t, J = 7.3 Hz, 3H, CH3). 13C NMR (101 MHz,
DMSO‐d6) δ 170.62, 168.17, 165.35, 162.26, 158.10, 143.55, 135.92,
130.35, 118.89, 117.63, 112.88, 105.39, 77.36, 75.06, 74.01, 55.97,
37.40, 32.50, 31.42, 23.19, 13.75. HRMS (ESI) m/z: calcd. for
C
22H28N5O4S [M+H]+ 458.1862; found, 458.1867.
4‐{2‐[(E)‐3‐Methylbenzylidene]hydrazinyl}‐2‐(propylthio)‐7‐
[(1R,2S,3R,4S)‐2,3,4‐trihydroxycyclopentyl]‐5,7‐dihydro‐6H‐
pyrrolo‐[2,3‐d]pyrimidin‐6‐one (23)
The title compound 23 (261 mg) was prepared from 10 (356 mg,
1 mmol) and 3‐methylbenzaldehyde (144 mg, 1.2 mmol) using the
procedure described for compound 11 in 57.4% yield as a white solid,
m.p. 149.6–150.9°C. 1H NMR (400 MHz, DMSO‐d6) δ 11.55 (d,
J = 22.8 Hz, 1H, NH), 8.08 (d, J = 70.2 Hz, 1H, N═CH), 7.53 (s, 1H,
Ph–H), 7.47–7.41 (m, 1H, Ph–H), 7.33 (td, J = 7.6, 1.7 Hz, 1H, Ph–H),
7.23 (d, J = 7.6 Hz, 1H, Ph–H), 4.95–4.77 (m, 1H, OH), 4.63 (s, 1H,
OH), 4.59–4.44 (m, 1H, OH), 4.27 (p, J = 8.0 Hz, 1H, CH), 4.13–3.96,
3.64 (m, 3H, CH, CH2), 3.80 (dq, J = 8.3, 4.6 Hz, 1H, CH), 3.60 (dd,
J = 5.1, 3.4 Hz, 1H, CH), 3.00 (ddt, J = 27.8, 13.8, 6.9 Hz, 2H, CH2),
2.43 (ddd, J = 10.3, 8.7, 4.4 Hz, 1H, CH2), 2.35 (s, 3H, CH3), 1.68 (h,
J = 7.3 Hz, 2H, CH2), 1.21 (dt, J = 13.1, 3.7 Hz, 1H, CH2), 0.98 (t,
J = 7.3 Hz, 3H, CH3). 13C NMR (101 MHz, DMSO‐d6) δ 170.67,
168.11, 162.23, 158.01, 143.53, 138.54, 134.59, 130.99, 129.19,
127.56, 124.61, 105.45, 77.34, 75.03, 73.96, 55.96, 37.42, 32.48,
31.48, 23.20, 21.38, 13.75. HRMS (ESI) m/z: calcd. for C22H28N5O4S
[M+H]+ 458.1862; found, 458.1868.
C
21H26N5O5S [M+H]+ 460.1655; found, 460.1644.
4‐{2‐[(E)‐2,4‐Dihydroxybenzylidene]hydrazinyl}‐2‐(propylthio)‐7‐
[(1R,2S,3R,4S)‐2,3,4‐trihydroxycyclopentyl]‐5,7‐dihydro‐6H‐
pyrrolo‐[2,3‐d]pyrimidin‐6‐one (21)
The title compound 21 (204 mg) was prepared from 10 (356 mg,
1 mmol) and 2,4‐dihydroxybenzaldehyde (166 mg, 1.2 mmol) using
the procedure described for compound 11 in 43.1% yield as a gray
solid, m.p. 158.9–160.7°C. 1H NMR (400 MHz, DMSO‐d6) δ 11.45 (d,