5714
F. Epifano et al. / Bioorg. Med. Chem. Lett. 17 (2007) 5709–5714
146.9, 150.7, 152.2, 161.8, 176.7, 183.8; Anal. Calcd for
C30H30O6: C, 74.06; H, 6.21; O, 19.73. Found: C, 74.03, H,
6.19; O, 19.70.
17.5, 25.4, 26.2, 39.4, 55.8, 55.9, 65.9, 111.6, 114.4, 114.8,
117.7, 119.9, 121.9, 123.8, 123.9, 125.0, 126.6, 128.8, 131.3,
141.7, 142.5, 144.4, 146.2, 150.8, 151.2, 165.0; Anal. Calcd
for C27H32O5: C, 74.29; H, 7.39; O, 18.33. Found: C,
74.28, H, 7.37; O, 18.35.
4-(Acetylamino)phenyl (2E)-3-(4-{[(2E)-2,7-dimethyloc-
ta-2,6-dienyl]oxy}-3-methoxyphenyl)prop-2-enoate (15):
White solid; yield 90%; mp: 223–224 °C; IR (KBr): 1685,
Methyl (2E)-3-(3,4-bis{[(2E)-3-(4-{[(2E)-3,7-dimethyl-
octa-2,6- dienyl]oxy}-3-methoxyphenyl)prop-2-enoyl]ox-
y}phenyl)prop-2-enoate (20): Yellowish solid; yield 36%;
1
1630 cmꢀ1; H NMR (200 MHz, CDCl3 d): 1.59 (s, 3H),
1.66 (s, 3H), 1.74 (s, 3H), 2.09–2.23 (m, 4H), 1.59 (s, 3H),
2.18 (s, 3H), 3.92 (s, 3H), 4.66–4.69 (m, 2H), 4.99–5.12 (m,
2H), 5.48–5.57 (m, 1H), 6.47 (d, 1H, J = 12.8 Hz), 6.88 (d,
1H, J = 6.2 Hz) 7.11–7.27 (m, 4H), 7.54 (d, 1H,
J = 6.2 Hz), 7.80 (d, 2H, J = 12.8 Hz); 13C NMR
(50 MHz, CDCl3 d) 16.1, 17.5, 25.1, 25.6, 26.2, 39.4,
55.9, 65.8, 111.8, 114.1, 116.7, 119.8, 121.9, 122.4, 122.6,
123.8, 128.4, 131.3, 134.7, 141.6, 144.4, 146.3, 146.9, 150.8,
165.7, 167.6; Anal. Calcd for C28H33O5: C, 72.55; H, 7.18;
O, 17.26. Found: C, 72.57, H, 7.17; O, 17.24.
mp: 208–210 °C; IR (KBr): 1699, 1695 cmꢀ1
;
1H NMR
(200 MHz, CDCl3 d): 1.64 (s, 6H), 1.68 (s, 6H), 1.72 (s,
6H), 2.11–2.20 (m, 8H), 3.97 (s, 6H), 3.99 (s, 3H), 4.65–
4.72 (m, 4H), 5.05–5.11 (m, 2H), 5.50–5.56 (m, 2H), 6.40–
7.82 (m, 16H); 13C NMR (50 MHz, CDCl3 d) 16.5, 17.9,
25.4, 26.0, 39.3, 51.4, 55.9, 65.9, 111.6, 114.3, 116.7, 117.8,
119.4, 121.9, 122.0, 123.7, 126.6, 128.5, 129.5, 131.8, 134.8,
136.5, 141.3, 144.4, 144.6, 146.1, 146.4, 150.7, 164.8, 164.9,
168.2; Anal. Calcd for C50H58O10: C, 73.33; H, 7.14; O,
19.54. Found: C, 73.35, H, 7.11; O, 19.56.
Methyl 2-{[(2E)-3-(4-{[(2E)-2,7-dimethylocta-2,6-die-
nyl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}benzoate
(16): Yellow solid; yield 81%; mp: 182–183 °C; IR (KBr):
4-{[(2E)-3-(4-{[(2E)-3,7-Dimethylocta-2,6-dienyl]oxy}-
3-methoxyphenyl)prop-2-enoyl]oxy}phenyl (2E)-3-(4-{[(2E)-
3,7-dimethylocta-2,6-dienyl]oxy}-3-ethylphenyl)prop-2-
enoate (21): Bright yellow solid; yield 69%; mp: 232–233
(d) °C; IR (KBr): 1693 cmꢀ1; 1H NMR (200 MHz, CDCl3
d): 1.61 (s, 6H), 1.67 (s, 6H), 1.70 (s, 6H), 2.09–2.17 (m,
8H), 3.93 (s, 6H), 4.67–4.72 (m, 4H), 5.08–5.12 (m, 4H),
5.52–5.56 (m, 2H), 6.53–7.67 (m, 14H); 13C NMR
(50 MHz, CDCl3 d) 16.1, 17.4, 25.7, 26.3, 39.4, 55.8,
65.7, 111.8, 114.3, 116.8, 119.7, 119.8, 121.8, 123.8, 128.5,
131.5, 141.4, 144.2, 145.4, 146.2, 150.9, 165.8; Anal. Calcd
for C46H54O9: C, 77.02; H, 7.70; O, 15.28. Found: C,
77.01, H, 7.68; O,15.30.
6-{[(2E)-3-(4-{[(2E)-2,7-Dimethylocta-2,6-dienyl]oxy}-
3-methoxyphenyl)-1-methyleneprop-2-enyl]oxy}-9,10-dim-
ethylene-9,10- dihydroanthracen-2-yl (2E)-3-(4-{[(2E)-
2,7-dimethylocta-2,6-dienyl]oxy}-3- methoxyphenyl)prop-
2-enoate (22): Yellowish solid; yield 44%; mp: 252–255
(d) °C; IR (KBr): 1695 cmꢀ1; 1H NMR (200 MHz, CDCl3
d): 1.63 (s, 6H), 1.67 (s, 6H), 1.70 (s, 6H), 2.07–2.20 (m,
8H), 3.97 (s, 6H), 4.67–4.71 (m, 4H), 5.08–5.11 (m, 2H),
5.51–5.54 (m, 2H), 6.50–8.43 (m, 16H); 13C NMR
(50 MHz, CDCl3 d) 16.2, 17.6, 25.6, 26.1, 39.4, 55.9,
65.8, 111.6, 114.7, 116.7, 119.8, 120.3, 121.9, 123.8, 127.6,
128.4, 129.2, 131.3, 132.0, 137.6, 141.8, 144.4, 146.9,
150.7, 157.0, 165.7, 182.9; Anal. Calcd for C54H56O10: C,
74.98; H, 6.53; O, 18.50. Found: C, 74.95, H, 6.51; O,
18.46.
1
1698, 1695 cmꢀ1; H NMR (200 MHz, CDCl3 d): 1.67 (s,
3H), 1.69 (s, 3H), 1.75 (s, 3H), 2.10–2.18 (m, 4H), 3.98 (s,
3H), 3.99 (s, 3H), 4.68–4.72 (m, 2H), 5.06–5.09 (m, 1H),
5.50–5.53 (m, 1H), 6.54–8.08 (m, 9H); 13C NMR (50 MHz,
CDCl3 d) 16.4, 17.7, 25.7, 26.6, 27.5, 39.6, 51.4, 56.1, 67.9,
111.7, 114.2, 116.7, 119.4, 121.0, 121.9, 123.3, 123.9, 127.8,
128.6, 131.9, 132.1, 133.2, 135.2, 144.8, 146.2, 150.9, 155.0,
168.2, 168.5; Anal. Calcd for C28H32O6: C, 72.39; H, 6.94;
O, 20.66. Found: C, 72.40, H, 6.93; O, 20.68.
2-Methoxy-4-[(1E)-3-methoxy-3-oxoprop-1-enyl]phenyl
(2E)-3-(4-{[(2E)-2,7-dimethylocta-2,6-dienyl]oxy}-3-
methoxyphenyl)prop-2-enoate (17): Yellowish solid; yield
63%; mp: 159–161 °C; IR (KBr): 1695, 1692 cmꢀ1
;
1H
NMR (200 MHz, CDCl3 d): 1.62 (s, 3H), 1.69 (s, 3H), 1.75
(s, 3H), 2.11–2.20 (m, 4H), 3.92 (s, 3H), 3.94 (s, 3H), 3.97
(s, 3H), 4.68–4.71 (m, 2H), 5.09–5.11 (m, 1H), 5.49–5.53
(m, 1H), 6.51–7.89 (m, 7H); 13C NMR (50 MHz, CDCl3 d)
16.2, 17.6, 25.8, 26.9, 27.2, 39.4, 55.7, 55.9, 67.9, 111.7,
112.9, 114.0, 117.7, 118.4, 121.5, 123.6, 123.8, 123.9, 127.8,
128.5, 131.5, 132.1, 132.6, 139.2, 144.2, 144.7, 146.4, 150.5,
152.9, 164.9, 169.8; Anal. Calcd for C31H36O7: C,
71.52; H, 6.97; O, 21.51. Found: C, 71.50, H, 6.98; O,
21.50.
Methyl 4-{[(2E)-3-(4-{[(2E)-2,7-dimethylocta-2,6-die-
nyl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-3-meth-
oxybenzoate (18): Yellowish solid; yield 80%; mp: 162–
1
163 °C; IR (KBr): 1698, 1695 cmꢀ1; H NMR (200 MHz,
4-(5,7-Bis{[(2E)-3-(4-{[(2E)-3,7-dimethylocta-2,6-die-
nyl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-4-oxo-3,4-
dihydro-2H-chromen-2-yl)phenyl (2E)-3-(4-{[(2E)-3,7-
dimethylocta-2,6-dienyl]oxy}-3-methoxyphenyl)prop-2-
enoate (23): Yellowish solid; yield 31%; mp: 262–264 (d)
CDCl3d): 1.62 (s, 3H), 1.69 (s, 3H), 1.74 (s, 3H), 2.11–2.19
(m, 4H), 3.94 (s, 3H), 3.95 (s, 3H), 3.97 (s, 3H), 4.68–4.71
(m, 2H), 5.06–5.11 (m, 1H), 5.49–5.53 (m, 1H), 6.51–7.89
(m, 8H); 13C NMR (50 MHz, CDCl3 d) 16.5, 17.6, 25.6,
26.9, 27.3, 39.6, 51.2, 55.9, 56.0, 67.9, 111.7, 112.8, 114.0,
117.7, 121.9, 122.3, 123.6, 126.0, 127.7, 128.8, 131.5, 132.1,
144.8, 146.0, 146.2, 149.2, 150.4, 164.8, 166.2; Anal. Calcd
for C29H34O7: C, 70.43; H, 6.93; O, 22.64. Found: C,
70.41, H, 6.92; O, 22.65.
;
°C; IR (KBr): 1695, 1693 cmꢀ1 1H NMR (200 MHz,
CDCl3 d): 1.64 (s, 9H), 1.68 (s, 9H), 1.75 (s, 9H), 2.09–2.26
(m, 14H), 3.95 (s, 9H), 4.69–4.75 (m, 6H), 5.08–5.56 (m,
7H), 6.53–7.82 (m, 20H); 13C NMR (50 MHz, CDCl3 d)
16.3, 17.5, 25.6, 26.4, 39.3, 55.6, 65.9,78.5, 106.1 108.3,
111.7, 113.1, 114.5, 116.6, 116.7, 119.8, 121.6, 121.8, 123.9,
128.7, 130.0, 131.3, 135.9, 142.0, 144.4, 146.2, 150.1, 150.8,
153.5, 158.4, 165.2, 165.7, 169.3, 189.8; Anal. Calcd for
C75H84O14: C, 74.48; H, 7.00; O, 18.52. Found: C, 74.49,
H, 7.02; O, 18.51.
2-Methoxyphenyl (2E)-3-(4-{[(2E)-3,7-dimethylocta-2,6-
dienyl]oxy}-3-methoxyphenyl)prop-2-enoate (19): Orange
solid; yield 87%; mp: 145–147 °C; IR (KBr): 1696 cmꢀ1
;
1H NMR (200 MHz, CDCl3 d): 1.62 (s, 3H), 1.69 (s, 3H),
1.72 (s, 3H), 2.11–2.20 (m, 4H), 3.91 (s, 3H), 3.94 (s, 3H),
4.68–4.71 (m, 2H), 5.07–5.12 (m, 1H), 5.50–5.53 (m, 1H),
6.53–7.86 (m, 9H); 13C NMR (50 MHz, CDCl3 d) 16.2,
15. Tubaro, A.; Dri, P.; Del Bello, G.; Zilli, C.; Della Loggia, R.
Agents Actions. 1985, 17, 347.