Jin et al.
FULL PAPER
3β-[Methyl-[2-(4-methylphenoxy)ethyl]-amino]-
con-5-enine (7c) Yield 88%, white solid, m.p. 77-79
℃; purity, 98.8% (HPLC); 1H NMR (400 MHz, CDCl3)
δ: 0.93 (s, 3H), 1.05 (d, J=6.0 Hz, 3H), 2.44 (s, N-CH3,
3H), 2.28 (s, N-CH3, 3H), 2.22 (s, CH3, 3H), 3.00 (d,
J=10.4 Hz, 1H), 2.87 (t, J=6.0 Hz, 2H), 4.01 (t, J=
6.0 Hz, 2H), 5.35 (br s, 1H), 6.80 (d, J=8.0 Hz, 2H),
7.06 (d, J=8.0 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ:
38.7, 27.6, 55.8, 34.6, 141.9, 120.7, 32.0, 33.5, 41.2,
37.0, 22.0, 38.4, 50.4, 53.5, 24.5, 24.7, 50.0, 64.6, 19.5,
64.2, 14.8, 38.4, 63.2, 66.7, 52.3, 114.3 (C×2), 129.8
(C×2), 141.9, 156.7; ESIMS m/z: 477.3 [M+H]+.
3β-[[2-(4-Methoxyphenoxy)ethyl]methylamino]-
con-5-enine (7d) Yield 92%, white solid, m.p. 106-
49.9, 64.4, 19.5, 63.8, 14.2, 39.0, 63.8, 70.3, 51.9, 114.5,
121.9, 129.0, 134.2, 140.0, 157.2; ESIMS m/z: 553.4
[M+H]+.
3β-[Methyl-[2-(2-naphthoxy)ethyl]amino]con-5-
enine (7h) Yield 85%, yellow oil; purity, 97.1%
1
(HPLC); H NMR (400 MHz, CDCl3) δ: 0.94 (s, 3H),
1.19 (d, J=6.4 Hz, 3H), 2.44 (s, N-CH3, 3H), 2.28 (s,
N-CH3, 3H), 3.21 (d, J=10.4 Hz, 1H), 2.97 (t, J=6.0
Hz, 2H), 4.18 (t, J=6.0 Hz, 2H), 5.35 (br s, 1H), 7.14 (s,
1H), 7.15 (d, J=8.0 Hz, 1H), 7.32 (t, J=8.0 Hz, 1H),
7.43 (t, J=8.0 Hz, 1H), 7.70-7.76 (m, 3H); 13C NMR
(125 MHz, CDCl3) δ: 38.4, 27.1, 55.5, 34.6, 141.7,
120.6, 31.9, 33.5, 41.1, 37.0, 22.0, 38.1, 50.9, 53.3, 23.9,
24.8, 49.8, 64.1, 19.5, 63.3, 13.9, 38.9, 63.3, 66.6, 52.3,
106.6, 119.0, 123.5, 126.3, 126.7, 127.6, 128.9, 129.3,
134.5, 156.8; ESIMS m/z: 513.2 [M+H]+.
1
108 ℃; purity, 97.5% (HPLC); H NMR (400 MHz,
CDCl3) δ: 0.93 (s, 3H), 1.04 (d, J=6.0 Hz, 3H), 2.43 (s,
N-CH3, 3H), 2.21 (s, N-CH3, 3H), 3.76 (s, OCH3, 3H),
2.99 (d, J=10.4 Hz, 1H), 2.92 (t, J=6.0 Hz, 2H), 3.99
(t, J=6.0 Hz, 2H), 5.35 (br s, 1H), 6.81-6.85 (m, 4H);
13C NMR (125 MHz, CDCl3) δ: 38.6, 27.5, 55.7, 34.6,
141.9, 120.7, 32.0, 33.5, 41.1, 37.0, 22.0, 38.4, 50.5,
53.5, 24.5, 24.7, 50.0, 64.4, 19.5, 64.2, 14.7, 38.9, 63.3,
55.8, 67.3, 52.4, 114.5 (C×2), 120.7 (C×2), 153.7,
153.0; ESIMS m/z: 493.4 [M+H]+.
3β-[Methyl-[2-(1-naphthoxy)ethyl]amino]con-5-
enine (7i) Yield 90%, white solid, m.p. 133-135 ℃;
1
purity, 97.6% (HPLC); H NMR (400 MHz, CDCl3) δ:
0.95 (s, 3H), 1.04 (d, J=6.0 Hz, 3H), 2.45 (s, N-CH3,
3H), 2.22 (s, N-CH3, 3H), 3.00 (d, J=10.4 Hz, 1H),
3.06 (t, J=6.0 Hz, 2H), 4.21 (t, J=6.0 Hz, 2H), 5.37 (br
s, 1H), 6.80 (d, J=8.0 Hz, 1H), 7.34-7.49 (m, 4H),
7.78 (d, J=8.0 Hz, 1H), 8.26 (d, J=8.0 Hz, 1H); 13C
NMR (125 MHz, CDCl3) δ: 38.6, 27.5, 55.7, 34.8, 141.8,
120.8, 32.0, 33.4, 41.1, 37.0, 22.0, 38.4, 50.5, 53.5, 24.4,
24.9, 49.9, 64.4, 19.5, 64.1, 14.6, 39.1, 63.3, 67.2, 52.4,
104.5, 120.1, 122.1, 125.0, 125.6, 125.8, 126.3, 127.3,
134.4, 154.6; ESIMS m/z: 513.2 [M+H]+.
3β-[[2-(2,4-Dichlorophenoxy)ethyl]methyamino]-
con-5-enine (7e) Yield 79%, white solid, m.p. 73-75
℃; purity, 97.8% (HPLC); 1H NMR (400 MHz, CDCl3)
δ: 0.94 (s, 3H), 1.04 (d, J=6.4 Hz, 3H), 2.43 (s, N-CH3,
3H), 2.21 (s, N-CH3, 3H), 2.99 (d, J=10.4 Hz, 1H),
2.93 (t, J=6.0 Hz, 2H), 4.06 (t, J=6.0 Hz, 2H), 5.35 (br
s, 1H), 6.84 (d, J=8.0 Hz, 1H), 7.16 (d, J=8.0 Hz, 1H),
7.34 (d, J=2.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ:
38.7, 27.6, 55.8, 34.8, 141.8, 120.8, 32.0, 33.5, 41.1,
37.0, 22.0, 38.4, 50.4, 53.5, 24.5, 24.8, 50.0, 64.6, 19.5,
64.3, 14.8, 39.2, 63.2, 68.7, 52.1, 113.9, 123.6, 125.6,
127.5, 129.9, 153.3; ESIMS m/z: 531.2 [M+H]+.
3β-[[2-(4-Chlorophenoxy)ethyl]methylamino]-
con-5-enine (7f) Yield 86%, white solid, m.p. 91-93
℃; purity, 98.0 % (HPLC); 1H NMR (400 MHz, CDCl3)
δ: 0.93 (s, 3H), 1.04 (d, J=6.0 Hz, 3H), 2.42 (s, N-CH3,
3H), 2.22 (s, N-CH3, 3H), 2.99 (d, J=10.4 Hz, 1H),
2.88 (t, J=6.0 Hz, 2H), 4.00 (t, J=6.0 Hz, 2H), 5.35 (br
s, 1H), 6.82 (d, J=8.8 Hz, 2H), 7.21 (d, J=8.8 Hz, 1H);
13C NMR (125 MHz, CDCl3) δ: 38.7, 27.6, 55.8, 34.6,
141.8, 120.8, 32.0, 33.5, 41.1, 37.0, 22.0, 38.4, 50.4,
53.5, 24.5, 24.7, 50.0, 64.5, 19.5, 64.2, 14.8, 38.9, 63.2,
67.1, 52.2, 115.7 (C×2), 129.2 (C×2), 125.4, 157.4;
ESIMS m/z: 497.3 [M+H]+.
3β-[[2-(4-Chloro-1-naphthoxy)ethyl]methyl-
amino]con-5-enine (7j) Yield 85%, yellow oil, purity,
1
97.3% (HPLC); H NMR (400 MHz, CDCl3) δ: 0.95 (s,
3H), 1.05 (d, J=6.0 Hz, 3H), 2.47 (s, N-CH3, 3H), 2.23
(s, N-CH3, 3H), 3.00 (d, J=10.4 Hz, 1H), 3.05 (t, J=
6.0 Hz, 2H), 4.19 (t, J=6.0 Hz, 2H), 5.36 (br s, 1H),
6.71 (d, J=8.0 Hz, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.51 (t,
J=8.0 Hz, 1H), 7.60 (t, J=8.0 Hz, 1H), 8.18 (d, J=8.0
Hz, 1H), 8.29 (d, J=8.0 Hz, 1H); 13C NMR (125 MHz,
CDCl3) δ: 38.5, 27.4, 55.7, 34.8, 141.8, 120.8, 32.0,
33.5, 41.1, 37.0, 22.0, 38.4, 50.5, 53.5, 24.3, 24.9, 49.9,
64.2, 19.5, 64.2, 14.5, 39.0, 63.5, 67.5, 52.3, 104.6,
122.5, 123.1, 124.2, 125.7, 125.7, 126.6, 127.4, 131.3,
153.8; ESIMS m/z: 547.4 [M+H]+.
3β-[[2-(2-Methoxyphenoxy)ethyl]methylamino]-
con-5-enine (7k) Yield 82%, yellow oil. purity, 97.4%
1
(HPLC); H NMR (400 MHz, CDCl3) δ: 0.93 (s, 3H),
1.05 (d, J=6.0 Hz, 3H), 2.41 (s, N-CH3, 3H), 2.22 (s,
N-CH3, 3H), 3.00 (d, J=10.4 Hz, 1H), 2.96 (t, J=6.0
Hz, 2H), 4.10 (t, J=6.0 Hz, 2H), 5.34 (br s, 1H), 6.87-
6.92 (m, 4H); 13C NMR (125 MHz, CDCl3) δ: 38.6, 27.5,
55.8, 34.6, 141.8, 120.7, 32.0, 33.4, 41.1, 37.0, 22.0,
38.4, 50.4, 53.5, 24.4, 24.6, 49.9, 64.4, 19.5, 64.2, 14.7,
38.9, 63.3, 67.3, 52.1, 55.8, 111.7, 112.9, 120.8, 121.0,
148.3, 149.3; ESI-MS m/z: 493.4 [M+H]+.
3β-[[2-(2,4-Dinitrophenoxy)ethyl]methylamino]-
con-5-enine (7g) Yield 90%, white solid. m.p. 145-
1
147 ℃; purity, 97.8 % (HPLC); H NMR (400 MHz,
CDCl3) δ: 0.93 (s, 3H), 1.05 (d, J=6.0 Hz, 3H), 2.37 (s,
N-CH3, 3H), 2.25 (s, N-CH3, 3H), 3.12 (d, J=10.4 Hz,
1H), 2.97 (t, J=6.0 Hz, 2H), 4.27 (t, J=6.0 Hz, 2H),
5.35 (br s, 1H), 7.23 (d, J=8.8 Hz, 1H), 8.42 (d,
J=8.8 Hz, 1H), 8.76 (d, J=2.0 Hz, 1H); 13C NMR (125
MHz, CDCl3) δ: 38.3, 27.3, 55.6, 34.7, 141.5, 120.9,
32.0, 33.5, 41.1, 37.0, 22.0, 38.3, 50.7, 53.4, 24.1, 24.8,
Bioassay procedures for AChE inhibition
The procedure of testing AChE inhibiting activity
was same with those reported in our previous paper.[7]
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© 2013 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2013, 31, 1228—1233