E. Potter et al. / Bioorg. Med. Chem. xxx (2015) xxx–xxx
9
J = 7.1 Hz, 2H, COCH2), 5.32 and 5.39 (s, 2H each, 2 ꢂ NCH2),
7.22–7.78 (m, 8H, ArH; 2 ꢂ vinylic-H), 8.75 (s, 2H, ArH). 13C
NMR (75 MHz; CDCl3): d 14.10, 22.67, 24.94, 25.41, 29.34,
29.47, 29.68, 31.91, 33.57, 34.01, 44.73, 46.58, 122.98, 123.28,
127.58, 128.22, 132.60, 134.86, 135.79, 136.13, 136.27, 136.71,
121.87, 123.58, 128.18, 145.58, 145.82, 151.76, 172.26, 185.86.
IR (KBr; mmax): 3133, 2921, 2848, 1647, 1613, 1567, 1546, 1466,
1246, 1168, 1092, 992, 882, 773, 743, 621 cmꢀ1. UV (CHCl3;
kmax): 382 nm. ESI-HRMS (amu): calcd C27H35NO4 [M+Na]:
460.2464; found [M+Na]: 460.2436.
149.64, 149.84, 154.43, 172.55, 188.11. IR (KBr;
mmax): 3056,
2955, 2918, 1849, 1670, 1650, 1621, 1588, 1578, 1560, 1471,
1427, 1274, 1167, 987, 787 cmꢀ1. UV (CHCl3; kmax): 334 nm.
ESI-HRMS (amu): calcd C33H45N3O2 [M+H]: 516.3590; found
[M+H]: 516.3560.
4.1.2.22. (3E,5E)-3,5-Bis(furan-2-ylmethylene)-1-tetradecanoyl-
piperidin-4-one (E4). Yellow powder; yield: 74%; mp 74–76 °C.
1H NMR (300 MHz; CDCl3): d 0.90 (br s, 3H, CH3); 1.10–1.40 (m,
20H, 10 ꢂ CH2), 1.62 (m, 2H, CH2), 2.44 (t, J = 6.9 Hz, 2H, COCH2),
4.98 and 5.06 (s, 2H each, 2 ꢂ NCH2), 6.54–6.60 (m, 2H, ArH),
6.77 (br s, 2H, ArH), 7.51 and 7.55 (s, 1H each, 2 ꢂ vinylic-H),
7.65 (br s, 2H, ArH). 13C NMR (75 MHz; CDCl3): d 14.12, 22.69,
24.84, 25.34, 29.13, 29.36, 29.48, 29.64, 31.92, 33.42, 33.87,
43.50, 46.14, 112.67, 112.79, 118.05, 118.46, 121.85, 123.57,
128.13, 128.44, 145.56, 145.87, 151.76, 172.26, 185.86. IR (KBr;
4.1.2.18. (3E,5E)-3,5-Bis(pyridin-2-ylmethylene)-1-stearoylpi-
peridin-4-one (D6).
Yellow powder; yield: 25%; mp 102–
104 °C. 1H NMR (300 MHz; CDCl3): d 0.90 (t, J = 6.3 Hz, 3H, CH3),
1.19–1.40 (m, 28H, 14 ꢂ CH2), 1.53–1.58 (m, 2H, CH2), 2.38 (t,
J = 7.5 Hz, 2H, COCH2), 5.33 and 5.39 (s, 2H each, 2 ꢂ NCH2),
7.24–7.28 (m, 2H, ArH), 7.52 (t, J = 7.1 Hz, 2H, ArH), 7.66–7.79
(m, 4H, ArH; 2 ꢂ vinylic-H), 8.76 (br s, 2H, ArH). 13C NMR
(75 MHz; CDCl3): d 14.13, 22.70, 25.42, 29.34, 29.27, 29.49, 29.62,
29.66, 29.71, 31.93, 33.59, 44.72, 46.59, 122.98, 123.29, 127.61,
128.25, 132.60, 134.88, 135.81, 136.15, 136.27, 136.72, 149.65,
149.87, 154.44, 172.49, 188.18. IR (KBr; v): 3056, 2955, 2918,
1849, 1650, 1622, 1588, 1578, 1560, 1471, 1427, 1275, 1167,
987, 787 cmꢀ1. UV (CHCl3; kmax): 334 nm. ESI-HRMS (amu): calcd
m
max): 2949, 2921, 2947, 1643, 1617, 1575, 1542, 1464, 1443,
1255, 1203, 1171, 982, 884, 757, 620 cmꢀ1. UV (CHCl3; kmax):
383 nm. ESI-HRMS (amu): calcd C29H39NO4 [M+Na]: 488.2777;
found [M+Na]: 488.2751.
4.1.2.23.
peridin-4-one (E5).
(3E,5E)-3,5-Bis(furan-2-ylmethylene)-1-palmitoylpi-
Yellow powder; yield: 51%; mp 84–
85 °C. 1H NMR (300 MHz; CDCl3): d 0.90 (t, J = 6.2 Hz, 3H, CH3);
1.24–1.27 (m, 24H, 12 ꢂ CH2), 1.62 (quintet, J = 6.2 Hz, 2H, CH2),
2.45 (t, J = 6.4 Hz, 2H, COCH2), 5.00 and 5.05 (s, 2H each, 2 ꢂ NCH2),
6.58 (br s, 2H, ArH), 6.77–6.78 (m, 2H, ArH), 7.54 (br s, 2H,
2 ꢂ vinylic-H), 7.65 (br s, 2H, ArH). 13C NMR (75 MHz; CDCl3): d
14.09, 22.67, 25.34, 29.34, 29.47, 29.64, 29.67, 31.91, 33.38,
43.54, 46.12, 112.71, 118.31, 121.89, 123.59, 128.33, 145.69,
C35H49N3O2 [M+H]: 544.3903; found [M+H]: 544.3860.
4.1.2.19. (3E,5E)-1-Oleoyl-3,5-bis(pyridin-2-ylmethylene)piperi-
din-4-one (D7).
Orange solid; yield: 45%; mp 72–74 °C. 1H
NMR (300 MHz; CDCl3): d 0.88 (dist. t, 3H, CH3), 1.18–1.40 (m,
22H, 11 ꢂ CH2), 1.49–1.57 (m, 2H, CH2), 1.99–2.05 (m, 4H,
2 ꢂ CH2), 2.38 (t, J = 7.7 Hz, 2H, COCH2), 5.31–5.38 (m, 6H,
2 ꢂ NCH2; 2 ꢂ Z-vinylic), 7.24–7.28 (m, 2H, ArH), 7.51 (t,
J = 6.4 Hz, 2H, ArH), 7.65–7.77 (m, 4H, ArH; 2 ꢂ vinylic-H), 8.74
(br s, 2H, ArH). 13C NMR (75 MHz; CDCl3): d 14.17, 22.65, 25.38,
27.20, 28.96, 29.11, 29.21, 29.42, 29.46, 29.50, 29.68, 29.75, 31.88,
32.58, 33.53, 44.72, 46.57, 122.97, 123.27, 127.57, 128.21, 129.76,
129.93, 132.60, 134.82, 135.79, 136.14, 136.29, 136.70, 149.63,
151.77, 172.28, 185.82. IR (KBr; mmax): 2949, 2920, 2848, 1647,
1613, 1567, 1469, 1256, 1245, 1169, 1093, 992, 774, 744,
622 cmꢀ1. UV (CHCl3; kmax): 385 nm. ESI-HRMS (amu): calcd
C31H43NO4 [M+Na]: 516.3090; found [M+Na]: 516.3047.
4.1.2.24. (3E,5E)-3,5-Bis(furan-2-ylmethylene)-1-stearoylpiperi-
din-4-one (E6).
Yellow powder; yield: 86%; mp 82–84 °C. 1H
NMR (300 MHz; CDCl3): d 0.90 (t, J = 5.9 Hz, 3H, CH3); 1.25–1.28
(m, 28H, 14 ꢂ CH2), 1.63 (quintet, J = 7.0 Hz, 2H, CH2), 2.44 (t,
J = 7.5 Hz, 2H, COCH2), 4.98 and 5.07 (s, 2H each, 2 ꢂ NCH2),
6.55–6.60 (m, 2H, ArH), 6.78 (br s, 2H, ArH), 7.52 and 7.56 (s, 1H
each, vinylic-H), 7.65 (br s, 2H, ArH). 13C NMR (75 MHz; CDCl3): d
14.12, 22.69, 25.34, 29.37, 29.49, 29.66, 29.70, 31.93, 33.43,
43.49, 46.14, 112.66, 112.79, 118.03, 118.44, 121.84, 123.57,
128.17, 128.47, 145.55, 145.86, 151.78, 172.21, 185.91. IR (KBr;
149.80, 154.41, 172.50, 188.08. IR (KBr; mmax): 2990, 2923, 2851,
1676, 1640, 1582, 1560, 1465, 1428, 1273, 1164, 986, 939, 790,
746 cmꢀ1. UV (CHCl3; kmax): 334 nm. ESI-HRMS (amu): calcd
C35H47N3O2 [M+H]: 542.3747; found [M+H]: 542.3703.
4.1.2.20. (3E,5E)-1-Butyryl-3,5-bis(furan-2-ylmethylene)piperi-
din-4-one (E2).
Yellow powder; yield: 66%; mp 116–118 °C.
1H NMR (300 MHz; CDCl3): d 0.95 (t, J = 7.4 Hz, 3H, CH3), 1.68 (sex-
tet, J = 7.4 Hz, 2H, CH2), 2.43 (t, J = 7.5 Hz, 2H, COCH2), 4.98 and 5.07
(br s, 2H each, 2 ꢂ NCH2), 6.54–6.60 (m, 2H, ArH), 6.78 (br s, 2H,
ArH), 7.52 and 7.55 (s, 1H each, 2 ꢂ vinylic-H), 7.65 (br s, 2H,
ArH). 13C NMR (75 MHz; CDCl3): d 13.95, 18.69, 35.20, 43.44,
46.11, 112.66, 112.79, 118.05, 118.44, 121.87, 123.53, 128.13,
m
max): 2952, 2920, 2847, 1643, 1617, 1577, 1543, 1463, 1444,
1254, 1198, 1171, 982, 757, 620 cmꢀ1. UV (CHCl3; kmax): 382 nm.
ESI-HRMS (amu): calcd
[M+Na]: 544.3359.
C33H47NO4 [M+Na]: 544.3403; found
128.46, 145.59, 145.87, 151.77, 171.96, 185.92. IR (KBr;
mmax):
4.1.2.25. (3E,5E)-3,5-Bis(furan-2-ylmethylene)-1-oleoylpiperi-
din-4-one (E7). Brownish/yellow low melting solid; yield:
3109, 1962, 1921, 2872, 2847, 1645, 1609, 1576, 1540, 1464,
1440, 1263, 1244, 1200, 1174, 1024, 977, 753, 621 cmꢀ1. UV (CHCl3;
kmax): 383 nm. ESI-HRMS (amu): calcd C19H19NO4 [M+Na]:
348.1212; found [M+Na]: 348.1189.
28%; 1H NMR (300 MHz; CDCl3): d 0.90 (t, J = 6.6 Hz, 3H, CH3),
1.10–1.40 (m, 22H, 11 ꢂ CH2), 1.63 (m, 2H, CH2), 2.02 (m, 4H,
CH2), 2.44 (t, J = 7.6 Hz, 2H, COCH2), 4.98 and 5.07 (s, 2H each,
2 ꢂ NCH2), 5.36 (m, 2H, Z vinylic-H), 6.58 (m, 2H, ArH), 6.78–6.79
(m, 2H, ArH), 7.52 and 7.56 (s, 1H each, 2 ꢂ vinylic-H), 7.65 (br s,
2H, ArH). 13C NMR (75 MHz; CDCl3): d 14.12, 22.68, 23.49, 27.22,
27.79, 28.95, 29.00, 29.06, 29.33, 29.53, 29.65, 29.72, 29.77,
31.91, 39.69, 44.08, 46.33, 112.70, 112.91, 118.36, 118.66, 122.31,
123.75, 127.40, 127.85, 129.77, 129.97, 145.82, 145.99, 151.48,
4.1.2.21. (3E,5E)-1-Dodecanoyl-3,5-bis(furan-2-ylmethylene)
piperidin-4-one (E3).
Orange powder; yield: 57%; mp 78–
81 °C. 1H NMR (300 MHz; CDCl3): d 0.90 (t, J = 6.1 Hz, 3H, CH3),
1.10–1.40 (m, 16H, 8 ꢂ CH2), 1.62 (quintet, J = 6.7 Hz, 2H, CH2),
2.44 (t, J = 7.6 Hz, 2H, COCH2), 4.98 and 5.06 (s, 2H each,
2 ꢂ NCH2), 6.55–6.60 (m, 2H, ArH), 6.77–6.78 (m, 2H, ArH),
7.52 and 7.55 (s, 1H each, 2 ꢂ vinylic-H), 7.65 (br s, 2H, ArH).
13C NMR (75 MHz; CDCl3): d 14.10, 22.67, 25.34, 29.32, 29.35,
29.47, 29.59, 31.90, 33.40, 43.52, 46.14, 112.72, 118.02, 118.43,
151.70, 168.48, 185.35. IR (KBr;
mmax): 3105, 2924, 2852, 1644,
1611, 1569, 1541, 1465, 1283, 1258, 1166, 1020, 988, 758,
622 cmꢀ1. UV (CHCl3; kmax): 383 nm. ESI-HRMS (amu): calcd
C33H43NO4 [M+Na]: 542.3246; found [M+Na]: 542.3198.