330
Chem. Pharm. Bull.
Vol. 63, No. 5 (2015)
(2H, m, CH2), 1.47–1.38 (2H, m, CH2). 13C-NMR (DMSO- 6.88 (1H, d, J=8.0Hz, H-5′), 6.83 (1H, d, J=15.5Hz, H-5),
d6, 100MHz) δ: 165.0, 147.9, 147.6, 142.1, 139.1, 137.7, 130.9, 6.77 (1H, br s, H-5″), 6.05 (1H, d, J=15.0Hz, H-2), 6.02 (2H, s,
128.3, 128.2, 125.6, 125.2, 124.6, 122.6, 108.4, 105.6, 101.2, –OCH2O–), 3.37–3.28 (2H, m, NCH2), 2.64 (2H, t, J=7.4Hz,
38.4, 34.8, 28.8, 28.5. MS (EI) m/z: 349 [M]+. Anal. Calcd CH2). 13C-NMR (CD3OD, 100MHz) δ: 169.0, 149.8, 149.7,
for C22H23NO3: C, 75.62; H, 6.63; N, 4.01. Found: C, 75.48; H, 142.2, 140.3, 136.1, 136.0, 132.4, 125.9, 124.1, 123.8, 109.4,
6.66; N, 4.05.
106.7, 102.73, 102.70, 40.6, 27.9. MS (EI) m/z: 311 [M]+. Anal.
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-5-(3,4-methylene- Calcd for C17H17N3O3: C, 65.58; H, 5.50; N, 13.50. Found: C,
dioxyphenyl)-2E,4E-pentadienamide (11) Yield 56%. Yellow 65.31; H, 5.41; N, 13.46.
solid. mp 170–172°C. IR (KBr) cm−1: 3341, 1641, 1582, 1515,
N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5-(3,4-methylene-
1
1502, 1255. H-NMR (DMSO-d6, 400MHz) δ: 8.86 (1H, s, dioxyphenyl)-2E,4E-pentadienamide (15) Yield 70%. Yel-
OH), 8.43 (1H, br t, J=5.8Hz, NH), 7.27 (1H, d, J=1.6Hz, low solid. mp 114–117°C. IR (KBr) cm−1: 3360, 3290, 1661,
1
H-2′), 7.19 (1H, dd, J=15.0, 10.0Hz, H-3), 6.99 (1H, dd, J=8.1, 1641, 1590, 1500, 1246. H-NMR (DMSO-d6, 400MHz) δ:
1.6Hz, H-6′), 6.93 (1H, dd, J=15.5, 10.0Hz, H-4), 6.91 (1H, 10.49 (1H, br s, H-1″), 8.61 (1H, br s, OH), 8.16 (1H, br t,
d, J=8.1Hz, H-5′), 6.86 (1H, d, J=15.5Hz, H-5), 6.84 (1H, d, J=5.7Hz, NH), 7.26 (1H, d, J=1.6Hz, H-2′), 7.16 (1H, dd,
J=1.9Hz, H-2″), 6.71 (1H, d, J=8.0Hz, H-5″), 6.67 (1H, dd, J=15.0, 10.1Hz, H-3), 7.12 (1H, d, J=8.5Hz, H-7″), 7.04 (1H,
J=8.0, 1.9Hz, H-6″), 6.13 (1H, d, J=15.0Hz, H-2), 6.04 (2H, d, J=2.3Hz, H-2″), 6.99 (1H, dd, J=8.1, 1.6Hz, H-6′), 6.92
s, –OCH2O–), 4.25 (2H, d, J=5.8Hz, NCH2), 3.74 (3H, s, (1H, dd, J=15.5, 10.1Hz, H-4), 6.91 (1H, d, J=8.1Hz, H-5′),
OCH3). 13C-NMR (DMSO-d6, 100MHz) δ: 165.0, 147.9, 147.7, 6.85 (1H, d, J=15.5Hz, H-5), 6.84 (1H, d, J=2.3Hz, H-4″),
147.5, 145.5, 139.5, 137.9, 130.8, 130.2, 125.2, 124.4, 122.7, 6.59 (1H, dd, J=8.5, 2.3Hz, H-6″), 6.09 (1H, d, J=15.0Hz,
119.9, 115.2, 111.9, 108.4, 105.6, 101.2, 55.6, 42.1. MS (EI) m/z: H-2), 6.04 (2H, s, –OCH2O–), 3.44–3.33 (2H, m, NCH2),
353 [M]+. Anal. Calcd for C20H19NO5: C, 67.98; H, 5.42; N, 2.76 (2H, t, J=7.4Hz, CH2). 13C-NMR (DMSO-d6, 100MHz)
3.96. Found: C, 67.70; H, 5.36; N, 3.93.
δ: 165.1, 150.2, 147.9, 147.7, 139.2, 137.7, 130.9, 130.8, 127.9,
N-[2-(4-Hydroxyphenyl)ethyl]-5-(3,4-methylenedioxy- 125.3, 124.7, 123.1, 122.6, 111.6, 111.3, 110.8, 108.4, 105.6,
phenyl)-2E,4E-pentadienamide (12) Yield 69%. Pale orange 102.2, 101.2, 25.4. MS (EI) m/z: 376 [M]+. Anal. Calcd for
solid. mp 193–194°C. IR (KBr) cm−1: 3281, 1641, 1614, 1602, C22H20N2O4: C, 70.20; H, 5.36; N, 7.44. Found: C, 70.17; H,
1546, 1501, 1240. 1H-NMR (DMSO-d6, 400MHz) δ: 9.18 5.60; N, 7.40.
(1H, br s, OH), 8.09 (1H, br t, J=5.6Hz, NH), 7.24 (1H, d,
5-(3,4-Methylenedioxyphenyl)-N-[2-(2-pyridinyl)ethyl]-
J=1.6Hz, H-2′), 7.12 (1H, dd, J=15.0, 10.1Hz, H-3), 6.98 (2H, 2E,4E-pentadienamide (16) Yield 66%. Colorless solid. mp
d, J=8.4Hz, H-2″ and H-6″), 6.98–6.95 (1H, m, H-6′), 6.89 144–145°C. IR (KBr) cm−1: 3299, 1643, 1607, 1540, 1499,
1
(1H, dd, J=15.5, 10.1Hz, H-4), 6.88 (1H, d, J=8.0Hz, H-5′), 1256. H-NMR (DMSO-d6, 400MHz) δ: 8.49–8.46 (1H, m,
6.82 (1H, d, J=15.5Hz, H-5), 6.66 (2H, d, J=8.4Hz, H-3″ and H-6″), 8.13 (1H, brt, J=5.6Hz, NH), 7.68 (1H, td, J=7.6,
H-5″), 6.05 (1H, d, J=15.0Hz, H-2), 6.02 (2H, s, –OCH2O–), 1.9Hz, H-4″), 7.25–7.18 (2H, m, H-3″ and H-5″), 7.23 (1H,
3.31–3.23 (2H, m, NCH2), 2.61 (2H, t, J=7.4Hz, CH2). d, J=1.7Hz, H-2′), 7.12 (1H, dd, J=15.0, 9.9Hz, H-3), 6.97
13C-NMR (DMSO-d6, 100MHz) δ: 165.1, 155.6, 147.9, 147.7, (1H, dd, J=8.1, 1.7Hz, H-6′), 6.89 (1H, dd, J=15.4, 9.9Hz,
139.2, 137.8, 130.9, 129.5, 129.4, 125.3, 124.6, 122.6, 115.1, H-4), 6.88 (1H, d, J=8.1Hz, H-5′), 6.83 (1H, d, J=15.4Hz,
108.4, 105.6, 101.2, 40.7, 34.4. MS (EI) m/z: 337 [M]+. Anal. H-5), 6.03 (1H, d, J=15.0Hz, H-2), 6.02 (2H, s, –OCH2O–),
Calcd for C20H19NO4: C, 71.20; H, 5.68; N, 4.15. Found: C, 3.52–3.44 (2H, m, NCH2), 2.88 (2H, t, J=7.3Hz, CH2).
70.95; H, 5.69; N, 4.16.
13C-NMR (DMSO-d6, 100MHz) δ: 165.1, 159.1, 149.0, 147.9,
N-[2-(3,4-Dihydroxyphenyl)ethyl]-5-(3,4-methylenedioxy- 147.7, 139.2, 137.8, 136.4, 130.8, 125.2, 124.5, 123.1, 122.6,
phenyl)-2E,4E-pentadienamide (13) Yield 64%. Pale orange 121.5, 108.4, 105.6, 101.2, 38.6, 37.4. MS (EI) m/z: 322 [M]+.
solid. mp 169–170°C. IR (KBr) cm−1: 3332, 3276, 1645, 1587, Anal. Calcd for C19H18N2O3: C, 70.79; H, 5.63; N, 8.69. Found:
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1503, 1255. H-NMR (DMSO-d6, 400MHz) δ: 8.70 (2H, br s, C, 70.71; H, 5.57; N, 8.69.
OH), 8.08 (1H, br t, J=5.4Hz, NH), 7.24 (1H, d, J=1.6Hz,
( )-5-(3,4-Methylenedioxyphenyl)-N-(1-phenylethyl)-2E,4E-
H-2′), 7.12 (1H, dd, J=14.9, 10.1Hz, H-3), 6.97 (1H, dd, J=8.1, pentadienamide (17) Yield 83%. Pale orange solid. mp
1.6Hz, H-6′), 6.90 (1H, dd, J=15.5, 10.1Hz, H-4), 6.89 (1H, 163–165°C. IR (KBr) cm−1: 3282, 1643, 1603, 1539, 1502,
d, J=8.1Hz, H-5′), 6.82 (1H, d, J=15.5Hz, H-5), 6.61 (1H, 1244. 1H-NMR (DMSO-d6, 100 MHz) δ: 8.47 (1H, brd,
d, J=8.0Hz, H-5″), 6.56 (1H, d, J=2.0Hz, H-2″), 6.42 (1H, J=8.1Hz, NH), 7.34–7.29 (4H, m, Ph), 7.26 (1H, d, J=1.6Hz,
dd, J=8.0, 2.0Hz, H-6″), 6.04 (1H, d, J=14.9Hz, H-2), 6.02 H-2′), 7.25–7.19 (1H, m, Ph), 7.15 (1H, dd, J=15.0, 10.2Hz,
(2H, s, –OCH2O–), 3.28–3.20 (2H, m, NCH2), 2.53 (2H, t, H-3), 6.99 (1H, dd, J=8.2, 1.6Hz, H-6′), 6.93 (1H, dd, J=15.5,
J=7.5Hz, CH2). 13C-NMR (DMSO-d6, 100MHz) δ: 165.0, 10.2Hz, H-4), 6.90 (1H, d, J=8.2Hz, H-5′), 6.85 (1H, d,
147.9, 147.7, 145.0, 143.5, 139.2, 137.7, 130.9, 130.2, 125.3, J=15.5Hz, H-5), 6.15 (1H, d, J=15.0Hz, H-2), 6.04 (2H, s,
124.6, 122.6, 119.2, 115.9, 115.5, 108.4, 105.6, 101.2, 40.7, 34.7. –OCH2O–), 5.01 (1H, dq, J=8.1, 7.0Hz, NCH), 1.38 (3H, d,
MS (EI) m/z: 353 [M]+. Anal. Calcd for C20H19NO5: C, 67.98; J=7.0Hz, CH3). 13C-NMR (DMSO-d6, 100MHz) δ: 164.3,
H, 5.42; N, 3.96. Found: C, 67.70; H, 5.37; N, 3.96.
147.9, 147.7, 144.7, 139.6, 137.9, 130.8, 128.2, 126.6, 126.0,
N-[2-(1H-Imidazol-4-yl)ethyl]-5-(3,4-methylenedioxy- 125.2, 124.5, 122.7, 108.4, 105.6, 101.2, 47.8, 22.5. MS (EI)
phenyl)-2E,4E-pentadienamide (14) Yield 76%. Pale orange m/z: 321 [M]+. Anal. Calcd for C20H19NO3: C, 74.75; H, 5.96;
solid. mp 193–194°C. IR (KBr) cm−1: 3287, 3267, 1641, 1602, N, 4.36. Found: C, 74.73; H, 5.96; N, 4.37.
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1539, 1503, 1260. H-NMR (DMSO-d6, 400MHz) δ: 8.11 (1H,
( )-N-(1-Methyl-3-phenylpropyl)-5-(3,4-methylenedioxy-
br t, J=5.6Hz, NH), 7.50 (1H, d, J=1.1Hz, H-2″), 7.23 (1H, d, phenyl)-2E,4E-pentadienamide (18) Yield 60%. Pale yel-
J=1.6Hz, H-2′), 7.13 (1H, dd, J=15.0, 10.0Hz, H-3), 6.97 (1H, low solid. mp 183–185°C. IR (KBr) cm−1: 3271, 1645, 1616,
dd, J=8.0, 1.6Hz, H-6′), 6.90 (1H, dd, J=15.5, 10.0Hz, H-4), 1540, 1502, 1252. 1H-NMR (DMSO-d4, 400MHz) δ: 7.95