Medicinal Chemistry Research
column chromatography on silica gel eluting with dichlor-
omethane: methanol (50: 1~30:1) to afford oil products.
Then a saturated solution of hydrochloric acid in ethanol
was added to the products and concentrated to get final
target compounds M1-M16 and M17-M25.
4.17–4.14 (m, 1H), 4.02–3.98 (m, 1H), 3.93 (q, J = 7.2 Hz,
2H), 3.69 (s, 3H), 3.57–3.26 (m, 11H), 3.13–3.02 (m, 3H),
2.80–2.69 (m, 2H), 2.34 (s, 1H), 2.25–2.16 (m, 2H),
2.00–1.92 (m, 1H), 1.73–1.32 (m, 12H), 1.02 (t, J = 7.2 Hz,
1H); 13C NMR (151 MHz, CDCl3) δ 173.75, 169.05,
152.28, 141.39, 122.84, 120.96, 118.19, 111.20, 62.78,
62.10, 60.19, 56.77, 56.46, 55.36, 53.77, 50.46, 44.60,
39.87, 34.97, 34.18, 32.58, 31.93, 29.70, 29.18, 28.29,
27.21, 22.69, 22.02, 21.10, 14.26. IR (KBr) ν: 3437, 2926,
2846, 1733, 1631, 1463 1278, 1233, 1028, 831; HR-MS
(ESI) m/z: Calculated for C30H47N4O4 [M + H]+ ms:
527.3592 found: 527.3598.
1
M1: yellow powder; yield: 64%; m.p.: 190–192 °C; H
NMR (600 MHz, DMSO-d6) δ: 10.12–9.97 (m, 2H), 7.27
(t, J = 8.4 Hz, 2H), 7.03 (d, J = 8.4 Hz, 2H), 6.88 (t, J =
8.4 Hz, 1H), 4.82–4.80 (m, 1H),4.38 (d, J = 16 .2 Hz, 1H),
4.21–4.15 (m, 1H), 3.82–3.75 (m, 2H), 3.58 (s, 3H),
3.55–3.51 (m, 2H), 3.45–3.14 (m, 9H), 2.92–2.75 (m, 2H),
2.37–2.29 (m, 3H), 2.16–2.01 (m, 2H), 1.85–1.44 (m, 11H);
13C NMR (151 MHz, CDCl3) δ 174.12, 168.84, 151.32,
129.08, 119.61, 116.02, 62.75, 62.11, 56.75, 56.45, 53.51,
51.48, 48.96, 44.56, 39.87, 34.95, 33.88, 32.61, 29.70,
29.22, 28.29, 27.22, 25.55, 21.98, 21.09, 14.12. IR (KBr) ν:
3415, 2956, 2854, 1723, 1657, 1456, 1384, 1261, 1020,
748, 681; HR-MS (ESI) m/z: Calculated for C28H43N4O3
[M + H]+ ms: 483.3330 found: 483.3329.
1
M5: yellow powder; yield: 64%; m.p.: 193–196 °C; H
NMR (600 MHz, D2O) δ: 7.14 (t, J = 7.8 Hz, 1H), 6.55 (d,
J = 7.8 Hz, 1H), 6.49 (d, J = 7.8 Hz, 1H), 6.48 (s, 1H),
4.10–3.97 (m, 2H), 3.90–3.79 (m, 1H), 3.67 (s, 3H),
3.51–3.49 (m, 1H), 3.47 (s, 3H), 3.37–2.85 (m, 12H),
2.80–2.69 (m, 2H), 2.33 (s, 1H), 2.25–2.18 (m, 2H),
2.02–1.92 (m, 1H), 1.84–1.32 (m, 12H); IR (KBr) ν: 3419,
2940, 2843, 2730, 1729, 1656, 1464, 1389, 1253, 1028,
826; ESI-MS, m/z: 513 {(M + 1)}.
1
M2: yellow powder; yield: 63%; m.p.: 192–194 °C; H
NMR (600 MHz, DMSO-d6) δ: 10.07 (d, J = 4.8 Hz, 2H),
7.37 (t, J = 8.4 Hz, 2H), 7.02 (d, J = 8.4 Hz, 2H), 6.87 (t, J =
8.4 Hz, 1H), 4.82–4.79 (m, 1H), 4.40 (d, J = 15.6 Hz, 1H),
4.20–4.15 (m, 1H), 3.82–3.75 (m, 2H), 3.58–3.52 (m, 4H),
3.45 (d, J = 7.2 Hz, 1H), 4.04 (q, J = 7.2 Hz, 2H),
3.39–3.11 (m, 7H), 2.93–2.77 (m, 2 H), 2.38–2.24 (m, 3H),
2.16–2.01 (m, 2H), 1.91–1.80 (m, 1H), 1.76–1.60 (m, 7H),
1.56–1.42 (m, 3H), 1.17 (t, J = 7.2 Hz, 3H). 13C NMR
(151 MHz, CDCl3) δ 173.71, 168.96, 151.28, 129.08,
119.65, 116.04, 62.94, 61.97, 60.22, 56.61, 56.36, 53.84,
53.47, 48.94, 44.79, 39.73, 35.05, 34.12, 32.39, 31.91,
30.31, 29.69, 28.95, 28.01, 21.96, 20.86, 14.26. IR (KBr) ν:
3412, 2955, 2860, 1722, 1662, 1472, 1274, 1042, 740, 688;
HR-MS (ESI) m/z: Calculated for C29H45N4O3 [M + H]+
ms: 497.3486 found: 497.3492.
1
M6: yellow powder; yield: 61%; m.p.: 188–191 °C; H
NMR (600 MHz, D2O) δ: 6.95 (d, J = 9.0 Hz, 2H), 6.93 (d,
J = 9.0 Hz, 2H), 4.33–4.31 (m, 1H), 4.15–4.12 (m, 1H),
4.02–3.98 (m, 1H), 3.69 (s, 3H), 3.51–3.02 (m, 16H),
2.80–2.69 (m, 2H), 2.35 (s, 1H), 2.27–2.16 (m, 2H),
2.01–1.92 (m, 1H), 1.77–1.31 (m, 12H); IR (KBr) ν: 3427,
2912, 2836, 1723, 1629, 1465, 1282, 1233, 1025, 851; ESI-
MS, m/z: 513 {(M + 1)}.
1
M7: yellow powder; yield: 63%; m.p.: 189–191 °C; H
NMR (600 MHz, D2O) δ: 7.13 (t, J = 8.4 Hz, 1H), 6.95 (s,
1H), 6.85 (d, J = 8.4.0 Hz), 6.82 (d, J = 8.4 Hz,), 4.32–4.29
(m, 1H), 4.15–4.10 (m, 1H), 4.03–3.99 (m, 1H), 3.82–3.00
(m, 16H), 2.80–2.70 (m, 2H), 2.34 (s, 1H), 2.34–2.24 (m,
2H), 2.00 –1.97 (m, 1H), 1.76–1.30 (m, 12H); IR (KBr) ν:
3424, 2939, 2858, 1719, 1657, 1461, 1387, 1269, 1021,
757, 691; ESI-MS, m/z: 517 {(M + 1)}.
1
M3: yellow powder; yield: 68%; m.p.: 187–189 °C; H
NMR (600 MHz, D2O) δ: 7.00 (t, J = 7.8 Hz, 1H), 6.95 (d,
J = 7.8 Hz, 1H), 6.88 (d, J = 8.4 Hz, 1H), 6.86 (t, J =
8.4 Hz, 1H), 4.32–4.30 (m, 1H), 4.16–4.13 (m, 1H),
4.03–3.99 (m, 1H), 3.76–3.01 (m, 16H), 2.80–2.67 (m, 2H),
2.35 (s, 1H), 2.27–2.16 (m, 2H), 2.00–1.94 (m, 1H),
1.76–1.32 (m, 12H), 13C NMR (151 MHz, CDCl3) δ
174.18, 169.04, 152.28, 141.41, 122.83, 120.96, 118.19,
111.21, 62.77, 62.13, 56.77, 56.47, 55.37, 53.78, 51.47,
50.47, 44.55, 39.96, 35.02, 33.91, 32.60, 29.70, 29.21,
28.28, 27.22, 22.69, 21.99, 21.13, 14.12. IR (KBr) ν: 3424,
2936, 2858, 1729, 1647, 1470, 1378, 1258, 1024, 837; HR-
MS (ESI) m/z: Calculated for C29H45N4O4 [M + H]+ ms:
513.3435 found: 513.3438.
1
M8: yellow powder; yield: 65%; m.p.: 189–192 °C; H
NMR (600 MHz, D2O) δ: 7.13 (t, J = 8.4 Hz, 1H), 6.95 (s,
1H), 6.85 (d, J = 8.4 Hz), 6.82 (d, J = 8.4.0 Hz), 4.20–4.17
(m, 1H), 4.06–3.91 (m, 1H), 3.92 (q, J = 7.2 Hz, 2H), 3.67
(s, 3H), 3.62–3.15 (m, 11H), 3.12–3.01 (m, 3H), 2.78–2.65
(m, 2H), 2.34 (s, 1H), 2.25–2.15 (m, 2H), 2.01–1.94 (m,
1H), 1.75–1.34 (m, 12H), 1.02 (t, J = 8.4 Hz, 3H); IR (KBr)
ν: 3423, 2936, 2857, 1731, 1654, 1489, 1456, 1399, 1261,
1026, 744, 686; ESI-MS, m/z: 542.45 {(M + Na+)}.
1
M9: yellow powder; yield: 64%; m.p.: 188–192 °C; H
NMR (600 MHz, D2O) δ: 6.94 (d, J = 7.2 Hz, 2H), (d, J =
7.2 Hz, 2H) 4.23–4.20 (m, 1H), 4.11–3.93 (m, 2H), 3.63–3.49
(m, 1H), 3.69 (s, 3H), 3.51–3.02 (m, 12H), 2.80–2.70 (m, 2H),
2.34 (s, 1H), 2.26–2.17 (m, 2H), 2.01–1.92 (m, 1H), 1.69–1.33
(m, 12H); IR (KBr) ν: 3424, 2922, 2841, 1738, 1663, 1460,
1264, 1023, 741; ESI-MS, m/z: 501 {(M + 1)}.
1
M4: yellow powder; yield: 62%; m.p.: 193–195 °C; H
NMR (600 MHz, D2O) δ: 7.07 (t, J = 7.8 Hz, 1H), 7.02 (d,
J = 7.8 Hz, 1H), 6.92 (d, J = 8.4 Hz, 1H), 6.86 (t, J =
7.8 Hz, 1H), 4.33–4.30 (m, 1H), 4.36–4.33 (m, 1H),