N-Ethyl-9-(4-ꢀ-D-allopyranosyloxyphenyl)-decahydroacridine-1,8-dione (2b). Yield 85%, yellow powder,
–1
mp 142–144ꢁC. IR (KBr, cm ): 3395, 2921, 2845, 1623, 1556, 1504, 1453, 1364, 1330, 1231, 1186, 1119, 1082, 1038, 947,
1
908, 840, 794, 703, 621, 546. H NMR (400 MHz, DMSO-d , ꢂ, ppm, J/Hz): 1.55–1.69 (4H, m, 2 ꢃ CH ), 1.76–1.88 (4H, m,
6
2
2 ꢃ CH ), 1.91–2.01 (4H, m, 2 ꢃ CH ), 2.21 (3H, t, J = 5.6, N-CH -CH ), 2.89 (2H, q, J = 6.0, N-CH ), 3.40–3.89 (6H, m),
2
2
2
3
2
4.46–5.00 (4H, br, 4OH), 5.01 (1H, d, J = 8.0, OCHO), 5.02 (1H, s, CH), 6.79 (2H, d, J = 8.8, ArH), 6.99 (2H, d, J = 8.8, ArH).
+
+
HR-MS-ESI m/z: calcd for C H NO [M + H] 500.2284, found 500.2283; C H NNaO [M + Na] 522.2014,
27 34
8
27 33
8
found 522.2015.
N-Propyl-9-(4-ꢀ-D-allopyranosyloxyphenyl)-decahydroacridine-1,8-dione (2c). Yield 80%, yellow powder,
–1
mp 144–145ꢁC. IR (KBr, cm ): 3407, 2925, 2855, 1930, 1623, 1563, 1506, 1459, 1383, 1229, 1185, 1123, 1082, 1041, 950,
1
836, 619, 547, 470. H NMR (400 MHz, DMSO-d , ꢂ, ppm, J/Hz): 1.58–1.64 (4H, m, 2 ꢃ CH ), 1.76–1.86 (4H, m, 2 ꢃ CH ),
6
2
2
1.93–2.02 (4H, m, 2 ꢃ CH ), 2.19–2.34 (3H, m, CH ), 2.26–2.34 (2H, m, CH ), 2.83–2.89 (2H, m, CH ), 3.39–3.89 (6H, m),
2
3
2
2
4.49–5.03 (4H, br, 4OH), 5.03 (1H, d, J = 6.4, OCHO), 5.04 (1H, s, CH), 6.79 (2H, d, J = 8.8, ArH), 6.98 (2H, d, J = 8.8, ArH).
+
+
HR-MS-ESI m/z: calcd for C H NO [M + H] 514.2441, found 514.2439; C H NNaO [M + Na] 536.2260,
28 36
8
28 35
8
found 536.2223.
N-(4-Methylphenyl)-9-(4-ꢀ-D-allopyranosyloxyphenyl)-decahydroacridine-1,8-dione (2d). Yield 82%, yellow
–1
powder, mp 148–150ꢁC. IR (KBr, cm ): 3414, 2923, 2848, 1724, 1633, 1566, 1507, 1453, 1363, 1286, 1233, 1182, 1113,
1
1082, 1040, 955, 910, 843, 619, 551. H NMR (400 MHz, DMSO-d , ꢂ, ppm, J/Hz): 1.58–1.67 (4H, m, 2 ꢃ CH ), 1.89–2.00
6
2
(4H, m, 2 ꢃ CH ), 2.17–2.22 (4H, m, 2 ꢃ CH ), 2.39 (3H, s, Ar-CH ), 3.38–3.93 (6H, m), 4.49–5.04 (4H, br, 4OH), 5.06 (1H,
2
2
3
d, J = 8.0, OCHO), 5.08 (1H, s, CH), 6.88 (2H, d, J = 8.8, ArH), 7.18 (3H, d, J = 8.8, ArH), 7.35–7.40 (3H, m, ArH).
+
+
HR-MS-ESI m/z: calcd for C H NO [M + H] 562.2441, found 563.2437; C H NNaO [M + Na] 584.2260,
32 36
8
32 35
8
found 584.2245.
N-Phenyl-9-(4-ꢀ-D-allopyranosyloxyphenyl)-decahydroacridine-1,8-dione (2e). Yield 74%, yellow powder,
–1
mp 151–152ꢁC. IR (KBr, cm ): 3413, 2922, 2890, 1631, 1565, 1501, 1453, 1363, 1286, 1233, 1182, 1133, 1081, 1039, 956,
1
909, 852, 713, 620, 550, 442. H NMR (400 MHz, DMSO-d , ꢂ, ppm, J/Hz): 1.59–1.84 (4H, m, 2 ꢃ CH ), 1.89–2.20 (4H, m,
6
2
2 ꢃ CH ), 2.20–2.24 (4H, m, 2 ꢃ CH ), 3.39–3.90 (6H, m), 4.48–5.03 (4H, br, 4OH), 5.06 (1H, d, J = 8.0, OCHO), 5.09 (1H,
2
2
s, CH), 6.89 (2H, d, J = 8.8, ArH), 7.19 (3H, d, J = 8.8, ArH), 7.54–7.61 (4H, m, ArH).
+
+
HR-MS-ESI m/z: calcd for C H NO [M + H] 548.2284, found 548.2271; C H NNaO [M + Na] 570.2014,
31 34
8
31 33
8
found 570.2097.
3,3,6,6-Tetramethyl-N-methyl-9-(4-ꢀ-D-allopyranosyloxyphenyl)-decahydroacridine-1,8-dione (2f). Yield 79%,
–1
yellow powder, mp 134–136ꢁC. IR (KBr, cm ): 3409, 2924, 2871, 1625, 1554, 1504, 1465, 1366, 1314, 1234, 1187, 1116,
1
1037, 945, 839, 619, 544. H NMR (400 MHz, DMSO-d , ꢂ, ppm, J/Hz): 0.95(6H, s, 2 ꢃ CH ), 0.99 (6H, s, 2 ꢃ CH ),
6
3
3
2.04–2.09 (4H, m, 2 ꢃ CH ), 2.39–2.44 (4H, m, 2 ꢃ CH ) 3.27 (3H, s, N-CH ), 3.38–3.90 (6H, m), 4.50–4.98 (4H, br, 4OH),
2
2
3
5.00 (1H, d, J = 8.0, OCHO), 5.03 (1H, s, CH), 6.78 (2H, d, J = 8.6, ArH), 6.99 (2H, d, J = 8.6, ArH).
+
+
HR-MS-ESI m/z: calcd for C H NO [M + H] 542.2754, found 542.2758; C H NNaO [M + Na] 564.2573,
30 40
8
30 39
8
found 564.2576.
3,3,6,6-Tetramethyl-N-ethyl-9-(4-ꢀ-D-allopyranosyloxyphenyl)-decahydroacridine-1,8-dione (2g). Yield 76%,
–1
yellow powder, mp 136–138ꢁC. IR (KBr, cm ): 3425, 2957, 2921, 2852, 1626, 1505, 1465, 1375, 1224, 1113, 1083, 1039,
1
988, 849, 619, 574. H NMR (400 MHz, DMSO-d , ꢂ, ppm, J/Hz): 0.89 (6H, s, 2 ꢃ CH ), 1.02 (6H, s, 2 ꢃ CH ), 2 .00–2.10
6
3
3
(4H, m, 2 ꢃ CH ), 2.15 (3H, t, J = 16.01, N-CH -CH ), 2.38–2.46 (4H, m, 2 ꢃ CH ), 2.70 (2H, q, J = 4.52, N-CH ), 3.42–3.89
2
2
3
2
2
(6H, m), 4.46–4.94 (4H, br, 4OH), 4.99 (1H, d, J = 8.0, OCHO), 5.01 (1H, s, CH), 6.78 (2H, d, J = 8.8, ArH), 7.00 (2H, d,
J = 8.8, ArH).
+
+
HR-MS-ESI m/z: calcd for C H NO [M + H] 556.2910, found 556.2915; C H NNaO [M + Na] 578.2730,
31 42
8
31 41
8
found 578.2734.
The sedative-hypnotic activities of the compounds were investigated by recording the number of spontaneous
locomotion in mice using an actophotometer [11, 12]. Fifty-four mice were randomized into 9 groups of 6 mice each (3 males
and 3 females). All the mice were placed in the multi-spontaneous activity recorder before the experiments to adapt to the
environment. Group A received saline by injection, group B received diazepam (20 mg/kg, i.p.), group C received helicid
(100 mg/kg, i.p.), and groups 2a–2g received the synthesized compounds (100 mg/kg, i.p.). When testing, the prepared solutions
were injected into the mouse stomach with a syringe in a volume of 0.2 mL/10 g body weight, and the spontaneous activity
number was recorded for 5 min after 0, 30, 60, 90 and 120 min. The data were recorded as number of movements per minute.
509