768
X.-Z. Li et al.
(1H, d, J ¼ 8.4 Hz, H-14), 6.95 (1H, d,
J ¼ 8.4 Hz, H-13), 6.62 (1H, s, H-8), 5.40
(1H, t, J ¼ 6.0 Hz, H-16), 5.05 (1H, t,
J ¼ 6.0 Hz, H-20), 4.55 (2H, d, J ¼
6.0 Hz, H-15), 4.10 (1H, q, J ¼ 6.9 Hz,
H-6), 4.00 (2H, t, J ¼ 6.3 Hz, H-25), 2.36
(2H, t, J ¼ 7.2 Hz, H-27), 2.25–2.30 (4H,
m, H-28, 280), 2.02–2.07 (4H, m, H-
18,19), 1.81–1.83 (2H, m, H-26), 1.68
(3H, s, CH3-24), 1.62 (3H, s, CH3-23),
1.55 (3H, s, CH3-22), 1.44–1.47 (4H, m,
CH3-29, 290), 1.35–1.37 (2H, m, CH3-30),
1.33 (3H, d, J ¼ 6.9 Hz, CH3-7); HR-ESI-
MS: m/z 510.3330 [M þ H]þ (calcd for
C30H44O4N3, 510.3332).
was obtained from (E)-4-(3,7-dimethy-
locta-2,6-dienyloxy)-3-(3-morpholinopro-
poxy)benzaldehyde (0.401 g) (0.179 g,
20
35.0%). White powder, ½aꢀD 262.9
1
(c ¼ 0.60, MeOH); H NMR (300 MHz,
DMSO-d6) dH: 9.78 (1H, br s, NH-1), 8.26
(1H, s, NH-4), 7.17 (1H, br s, H-10), 7.07
(1H, d, J ¼ 8.4 Hz, H-14), 6.94 (1H, d,
J ¼ 8.4 Hz, H-13), 6.55 (1H, s, H-8), 5.40
(1H, t, J ¼ 6.0 Hz, H-16), 5.05 (1H, t,
J ¼ 6.0 Hz, H-20), 4.54 (2H, d, J ¼
6.0 Hz, H-15), 4.08 (1H, q, J ¼ 6.9 Hz,
H-6), 4.00 (2H, t, J ¼ 6.3 Hz, H-25),
3.55 (4H, t, J ¼ 4.5 Hz, H-29, 290), 2.40
(2H, t, J ¼ 6.9 Hz, H-27), 2.31–2.36
(4H, m, H-28, 280), 2.03–2.07 (4H, m,
H-18, 19), 1.84–1.86 (2H, m, H-26), 1.68
(3H, s, CH3-24), 1.62 (3H, s, CH3-23),
1.55 (3H, s, CH3-22), 1.30 (3H, d,
J ¼ 6.9 Hz, CH3-7); HR-ESI-MS: m/z
512.3120 [M þ H]þ (calcd for C29H42O5
N3, 512.3124).
3.8 PJ1475 (16)
By following the same procedure as
described for the preparation of 12, 16
was obtained from (E)-4-(3,7-dimethy-
locta-2,6-dienyloxy)-3-(3-(4-methylpiper-
idin-1-yl)propoxy)benzaldehyde (0.399 g)
20
(0.155 g, 30.1%). White powder, ½aꢀD
260.8 (c ¼ 0.49, MeOH); 1H NMR
(300 MHz, DMSO-d6) d: 9.78 (1H, br s,
NH-1), 8.35 (1H, s, NH-4), 7.06 (1H, br s,
H-10), 7.03 (1H, d, J ¼ 8.4 Hz, H-14),
6.95 (1H, d, J ¼ 8.4 Hz, H-13), 6.62 (1H,
s, H-8), 5.40 (1H, t, J ¼ 6.0 Hz, H-16),
5.05 (1H, t, J ¼ 6.0 Hz, H-20), 4.55 (2H, d,
J ¼ 6.0 Hz, H-15), 4.10 (1H, q,
J ¼ 6.9 Hz, H-6), 4.00 (2H, t, J ¼ 6.3 Hz,
H-25), 2.79 (2H, t, J ¼ 11.3 Hz, H-28,
280), 2.38 (2H, t, J ¼ 7.2 Hz, H-27), 2.03–
2.07 (4H, m, H-18, 19), 1.81–1.83 (2H, m,
H-28, 280), 1.82–1.84 (2H, m, H-26), 1.68
(3H, s, CH3-24), 1.62 (3H, s, CH3-23),
1.55 (3H, s, CH3-22), 1.52 (2H, br s, CH3-
29, 290), 1.32 (3H, d, J ¼ 6.9 Hz, CH3-7),
1.29–1.31 (1H, m, H-30), 1.08–1.11 (2H,
m, H-29, 290), 0.86 (3H, d, J ¼ 6.3 Hz,
CH3-31); HR-ESI-MS: m/z 524.3485
[M þ H]þ (calcd for C31H46O4N3,
524.3488).
3.10 PJ1477 (18)
By following the same procedure as
described for the preparation of 12, 18
was obtained from (E)-4-(3,7-dimethy-
locta-2,6-dienyloxy)-3-(3-(4-methylpiper-
azin-1-yl)propoxy)benzaldehyde (0.414 g)
20
(0.202 g, 38.6%). White powder, ½aꢀD
257.1 (c ¼ 0.71, MeOH); 1H NMR
(300 MHz, DMSO-d6) dH: 9.78 (1H, br
s, NH-1), 8.35 (1H, s, NH-4), 7.06 (1H,
br s, H-10), 7.03 (1H, d, J ¼ 8.4 Hz, H-
14), 6.95 (1H, d, J ¼ 8.4 Hz, H-13), 6.62
(1H, s, H-8), 5.40 (1H, t, J ¼ 6.0 Hz, H-
16), 5.05 (1H, t, J ¼ 6.0 Hz, H-20), 4.54
(2H, d, J ¼ 6.0 Hz, H-15), 4.10 (1H, q,
J ¼ 6.9 Hz, H-6), 4.00 (2H, t, J ¼ 6.3 Hz,
H-25), 2.38–2.42 (2H, m, H-27), 2.27–
2.33(8H, m, H-28, 280, 29, 290), 2.12 (2H,
s, CH3-30), 2.03–2.07 (4H, m, H-18, 19),
1.81–1.83 (2H, m, H-26), 1.68 (3H, s,
CH3-24), 1.62 (3H, s, CH3-23), 1.55 (3H,
s, CH3-22), 1.32 (3H, d, J ¼ 6.9 Hz,
CH3-7); HR-ESI-MS: m/z 525.3441
[M þ H]þ (calcd for C30H45O4N4,
525.3441).
3.9 PJ1476 (17)
By following the same procedure as
described for the preparation of 12, 17