A.A. Wube et al. / European Journal of Medicinal Chemistry 46 (2011) 2091e2101
2099
H-10), 6.40 (dt, J ¼ 14.6, 6.8 Hz, 1H, H-20), 6.37 (s, 1H, H-3), 4.82 (d,
4J ¼ 2.4 Hz, 2H, NeCH2eChCH), 2.48 (t, 4J ¼ 2.4 Hz, 1H,
NeCH2eChCH), 2.29 (q, J ¼ 6.8 Hz, 2H, H-30), 1.50 (quint, J ¼ 7.2 Hz,
2H, H-40),1.36e1.22 (m,14H, H-50e110), 0.87 (t, J ¼ 6.8 Hz, 3H, H-120)
NeCH2eCH3), 1.38e1.21 (m, 16H, H-50e120), 0.87 (t, J ¼ 6.4 Hz, 3H, H-
130). 13C NMR: 177.5 (C-4), 151.8 (C-2), 142.3 (C-20), 140.2 (C-8a), 132.2
d
(C-7), 126.9 (C-4a), 126.8 (C-5), 123.2 (C-10), 123.2 (C-6), 115.3 (C-8),
109.6 (C-3), 42.5 (NeCH2eCH3), 33.1 (C-30), 31.9(C-110), 29.6 (C-100),
29.6 (C-90), 29.5 (C-80), 29.4 (C-70), 29.3 (C-60), 29.1 (C-50), 28.6 (C-40þ),
22.6 (C-120), 14.1 (C-130), 13.9 (NeCH2eCH3). ESI-MS m/z (%): [M þ 1]
354 (100), 326 [M þ 2eC2H5]þ, 312, 282, 268, 212, 198, 186, 172, 159,
117, 103.
13C NMR:
d
177.9 (C-4), 151.6 (C-2), 142.8 (C-20), 140.5 (C-8a), 132.3
(C-7), 126.6 (C-4a), 126.6 (C-5), 123.6 (C-10), 122.9 (C-6), 115.9 (C-8),
109.7 (C-3), 76.9 (NeCH2eChCH), 74.8 (NeCH2eChCH), 38.1
(NeCH2eChCH), 33.1 (C-30), 31.8 (C-100), 29.5 (C-90), 29.5 (C-80),
29.4 (C-70), 29.2 (C-60), 29.1 (C-50), 28.6 (C-40), 22.6 (C-110), 14.0
(C-120). ESI-MS m/z (%): [M þ 1]þ 350 (100), 310 [M þ 2eC3H3]þ, 294,
280, 236, 224, 210, 198, 184, 160, 107.
4.2.3.25. 1-(2-Propenyl)-2-[(1E)-tridecenyl]-4-(1H)-quinolone
(20c). Prepared from (E)-3-pentadecen-2-one (8) (1.5 g, 6.7 mmol)
inTHF (25 mL), LDA (3.4 mL, 6.7 mmol) and N-2-propenyl isatoic acid
anhydride (12) (1.02 g, 5.0 mmol) in THF (20 mL). 20c was formed as
yellow oil (0.76 g, 42%). IR (KBr, nmax cmꢀ1): 3443, 2924, 2853, 1624,
4.2.3.22. 1-Butyl-2-[(1E)-dodecenyl]-4-(1H)-quinolone (19e). Prepared
from (E)-3-tetradecen-2-one(7) (1.3g, 6.2 mmol)inTHF(25 mL), LDA
(3.1 mL, 6.2 mmol) and N-butyl isatoic acid anhydride (14) (1.02 g,
4.6 mmol) in THF (20 mL). 19e was formed as light yellow oil (0.81 g,
48%). IR (KBr, nmax cmꢀ1): 3424, 2925, 2854, 1623, 1598, 1486, 1423,
1599, 1486, 1422, 759. 1H NMR:
d
8.40 (dd, J ¼ 8.0, 1.6 Hz, 1H, H-5),
7.58 (td, J ¼ 8.0, 1.6 Hz, 1H, H-7), 7.35 (d, J ¼ 8.4 Hz, 1H, H-8), 7.31 (t,
J ¼ 7.6 Hz, 1H, H-6), 6.41 (s, 1H, H-3), 6.37 (dt, J ¼ 16.0, 6.4 Hz, 1H,
H-20), 6.31 (d, J ¼ 16.0 Hz,1H, H-10), 6.02 (ddt, J ¼ 17.2,10.7, 4.0 Hz,1H,
NeCH2eCH]CH2), 5.29 (d, J ¼ 10.8 Hz, 1H, NeCH2eCH]CHHb),
5.00 (d, J ¼ 17.2 Hz, 1H, NeCH2eCH]CHaH), 4.74 (d, J ¼ 2.0 Hz, 2H,
NeCH2eCH]CH2), 2.23 (q, J ¼ 6.8 Hz, 2H, H-30), 1.47 (m, 2H, H-40),
1.36e1.21 (m,16H, H-50e120), 0.86 (t, J ¼ 6.8 Hz, 3H, H-130).13C NMR:
1176, 759.1H NMR:
d
8.44 (d, J ¼ 8.4 Hz,1H, H-5), 7.64 (t, J ¼ 8.4 Hz,1H,
H-7), 7.46 (d, J ¼ 8.4 Hz, 1H, H-8), 7.34 (t, J ¼ 7.6 Hz, 1H, H-6), 6.44 (s,
1H, H-3), 6.37 (d, J ¼ 16.0 Hz,1H, H-10), 6.35 (dt, J ¼ 16.0, 6.4 Hz,1H, H-
20), 4.14 (t, J ¼ 8.0 Hz, 2H, NeCH2e(CH2)eCH3), 2.27 (q, J ¼ 7.2 Hz, 2H,
H-30),1.80 (quint, J ¼ 7.6 Hz, 2H, NeCH2eCH2eCH2eCH3),1.49 (quint,
J ¼ 7.2 Hz, 2H, H->40), 1.44 (m, 2H, Ne(CH2)2eCH2eCH3), 1.37e1.22
(m, 14H, H-50e110), 1.01 (t, J ¼ 7.6 Hz, 3H, Ne(CH2)3eCH3), 0.87 (t,
d
177.9 (C-4), 152.2 (C-2), 142.2 (C-20), 140.9 (C-8a), 132.1 (C-7), 131.1
(NeCH2eCH]CH2), 126.6 (C-4a), 126.5 (C-5), 123.5 (C-10), 123.3
(C-6), 117.5 (NeCH2eCH]CH2), 115.9 (C8), 109.3 (C-3), 50.0
(NeCH2eCH]CH2), 33.0 (C-30), 31.8 (C-110), 29.6 (C-100), 29.5 (C-90),
29.5 (C-80), 29.4 (C-70), 29.3 (C-60), 29.1 (C-50),þ28.6 (C-40), 22.6
(C-120), 14.0 (C-130). ESI-MS m/z (%): [M þ 1] 366 (100), 324
[M þ 2eC3H5]þ, 306, 224, 210, 198, 184, 146, 107.
J ¼ 6.8 Hz, 3H, H-120). 13C NMR:
d
177.5 (C-4),151.9 (C-2),142.0 (C-20),
140.4 (C-8a), 132.0 (C-7), 126.8 (C-4a),126.8 (C-5), 123.5 (C-10), 123.2
(C-6),115.4 (C-8),109.6 (C-3), 47.3 (NeCH2e(CH2)2eCH3), 33.1 (C-30),
31.8 (C-100), 30.6 (NeCH2eCH2eCH2eCH3), 29.5 (C-90), 29.5 (C-80),
29.4 (C-70), 29.2 (C-60), 29.1 (C-50), 28.6 (C-40), 22.6 (C-11), 19.9
(Ne(CH2)2eCH2eCH3),14.0 (C-140),13.7(Ne(CH2)3eCH3). ESI-MS m/
z (%): [M þ 1]þ 368 (100), 312, 298, 284, 256, 242, 198, 172, 159, 117,
105.
4.2.3.26. 1-Pentyl-2-[(1E)-tridecenyl]-4-(1H)-quinolone (20f). Prepared
from (E)-3-pentadecen-2-one (8) (1.5 g, 6.7 mmol) in THF (25 mL), LDA
(3.4 mL, 6.7 mmol) and N-pentyl isatoic acid anhydride (15) (1.17 g,
5.0 mmol) in THF (20 mL). 20f was formed as a yellow semisolid
(0.98 g, 50%). IR (KBr, nmax cmꢀ1): 3424, 2925, 2854, 1624, 1598, 1486,
4.2.3.23. 1-Pentyl-2-[(1E)-dodecenyl]-4-(1H)-quinolone (19f). Prepared
from (E)-3-tetradecen-2-one (7) (1.3 g, 6.2 mmol) in THF (25 mL), LDA
(3.1 mL, 6.2 mmol) and N-pentyl isatoic acid anhydride (15) (1.09 g,
4.6 mmol) in THF (20 mL). 19f was formed as a light yellow semisolid
(0.75 g, 43%). IR (KBr, nmax cmꢀ1): 3423, 2925, 2854, 1624, 1598, 1486,
1422, 759. 1H NMR:
d
8.43 (dd, J ¼ 8.0, 1.6 Hz, 1H, H-5), 7.62 (td, J ¼ 8.0,
1.6 Hz, 1H, H-7), 7.44 (d, J ¼ 8.4 Hz, 1H, H-8), 7.32 (t, J ¼ 7.6 Hz, 1H, H-6),
6.41 (d, J ¼ 15.2 Hz, 1H, H-10), 6.38 (s, 1H, H-3), 6.34 (dt, J ¼ 15.2, 6.8 Hz,
1H, H-20), 4.11 (t, J ¼ 8.4 Hz, 2H, NeCH2e(CH2)3eCH3), 2.26 (q,
J ¼ 6.8 Hz, 2H, H-30), 1.80 (m, 2H, NeCH2eCH2e(CH2)2eCH3), 1.49
(quint, J ¼ 7.2 Hz, 2H, H-40), 1.41e1.37 (m, 4H, Ne(CH2)2eCH2eCH2eCH3),
1.34e1.22 (m, 16H, H-50e120), 0.94 (t, J ¼ 6.8 Hz, 3H, Ne(CH2)4eCH3), 0.86
1422, 759. 1H NMR:
d
8.44 (dd, J ¼ 8.0, 1.6 Hz, 1H, H-5), 7.64 (td, J ¼ 8.0,
1.6 Hz, 1H, H-7), 7.45 (d, J ¼ 8.4 Hz, 1H, H-8), 7.34 (t, J ¼ 7.6 Hz, 1H, H-6),
6.42 (d, J ¼ 15.6 Hz, 1H, H-10), 6.39 (s, 1H, H-3), 6.36 (dt, J ¼ 15.6, 6.8 Hz,
1H, H-20), 4.11 (t, J ¼ 8.0 Hz, 2H, NeCH2e(CH2)3eCH3), 2.27
(q, J ¼ 6.8 Hz, 2H, H-30), 1.81 (m, 2H, NeCH2eCH2e(CH2)2eCH3),
(t, J ¼ 6.8 Hz, 3H, H-130). 13C NMR:
d
177.6 (C-4), 151.9 (C-2), 141.9 (C-20),
1.50 (quint,
J
¼
6.8 Hz, 2H, H-40), 1.44e1.39 (m, 4H,
140.4 (C-8a), 132.0 (C-7), 126.8 (C-4a), 126.8 (C-5), 123.5 (C-10), 123.1 (C-6),
115.4 (C-8), 109.7 (C-3), 47.5 (NeCH2e(CH2)3eCH3), 33.1 (C-30), 31.9 (C-
110), 29.6 (C-100), 29.6 (C-90), 29.5 (C-80), 29.4 (C-70), 29.3 (C-60), 29.1
(C-50), 28.7 (NeCH2eCH2e(CH2)2eCH3), 28.6 (C-40), 28.3
(Ne(CH2)2eCH2eCH2eCH3), 22.6 (C-120), 22.3 (Ne(CH2)3eCH2eCH3),
14.0 (C-130), 13.9 (Ne(CH2)4eCH3). ESI-MS m/z (%): [M þ 1]þ 396 (100),
324 [M þ 2eC5H11]þ, 310, 282, 256, 240, 198, 184, 159.
Ne(CH2)2eCH2eCH2eCH3), 1.32e1.23 (m, 14H, H-50e110), 0.94 (t,
J ¼ 6.8 Hz, 3H, Ne(CH2)4eCH3), 0.87 (t, J ¼ 6.8 Hz, 3H, H-120). 13C NMR:
d
177.6 (C-4), 151.9 (C-2), 142.0 (C-20), 140.4 (C-8a), 132.1 (C-7), 126.9 (C-
4a), 126.8 (C-5), 123.5 (C-10), 123.2 (C-6), 115.4 (C-8), 109.7 (C-3), 47.6
(NeCH2e(CH2)3eCH3), 33.1 (C-30), 31.9 (C-100), 29.6 (C-90), 29.6 (C-80),
29.4 (C-70), 29.3 (C-60), 29.1 (C-50), 28.8 (NeCH2eCH2e(CH2)2eCH3),
28.6 (C-40), 28.3 (Ne(CH2)2eCH2eCH2eCH3), 22.6 (Ce110), 22.3
(Ne(CH2)3eCH2eCH3), 14.0 (C-120), 13.9 (Ne(CH2)4eCH3). ESI-MS m/z
(%): [M þ 1]þ 382 (100), 310 [M þ 2eC5H11]þ, 284, 256, 240, 198, 184,
159.
4.2.3.27. 1-Propyl-2-[(1E)-tetradecenyl]-4-(1H)-quinolone
(21b). Prepared from (E)-3-hexadecen-2-one (9) (1.5 g, 6.3 mmol)
in THF (25 mL), LDA (3.2 mL, 6.3 mmol) and N-propyl isatoic acid
anhydride (11) (0.96 g, 4.7 mmol) in THF (20 mL). 21b was formed
as light yellow oil (0.87 g, 49%). IR (KBr, nmax cmꢀ1): 3422, 2924,
4.2.3.24. 1-Ethyl-2-[(1E)-tridecenyl]-4-(1H)-quinolone (20a). Prepared
from (E)-3-pentadecen-2-one (8) (1.5 g, 6.7 mmol) inTHF (25 mL), LDA
(3.4 mL, 6.7 mmol) and N-ethyl isatoic acid anhydride (10) (0.96 g,
5.0 mmol) in THF (20 mL). 20a was formed as a yellow semisolid
(0.79 g, 45%). IR (KBr, nmax cmꢀ1): 3422, 2925, 2853, 1626, 1597, 1487,
2853, 1625, 1598, 1485, 1422, 759. 1H NMR:
d
8.44 (d, J ¼ 8.0 Hz, 1H,
H-5), 7.64 (t, J ¼ 7.6 Hz, 1H, H-7), 7.45 (d, J ¼ 8.0 Hz, 1H, H-8), 7.34 (t,
J ¼ 7.6 Hz, 1H, H-6), 6.42 (s, 1H, H-3), 6.26 (d, J ¼ 14.8 Hz, 1H, H-10),
6.36 (dt, J ¼ 14.8, 6.4 Hz, 1H, H-20), 4.10 (t, J ¼ 8.0 Hz, 2H,
NeCH2eCH2eCH3), 2.27 (q, J ¼ 6.8 Hz, 2H, H-30), 1.84 (m, 2H,
NeCH2eCH2eCH3), 1.50 (m, 2H, H-40), 1.38e1.22 (m, 18H, H-
50e130),1.04 (t, J ¼ 7.2 Hz, 3H, Ne(CH2)2eCH3), 0.87 (t, J ¼ 7.2 Hz, 3H,
1423, 1177, 759. 1H NMR:
d
8.44 (dd, J ¼ 8.0, 1.6 Hz, 1H, H-5), 7.65 (td,
J ¼ 8.0, 1.6 Hz, 1H, H-7), 7.50 (d, J ¼ 8.4 Hz, 1H, H-8), 7.34 (t, J ¼ 7.6 Hz,
1H, H-6), 6.45 (d, J ¼ 15.2 Hz, 1H, H-10), 6.42 (s, 1H, H-3), 6.37 (dt,
J ¼ 15.2, 6.4 Hz, 1H, H-20), 4.25 (q, J ¼ 6.4 Hz, 2H, NeCH2eCH3), 2.27 (q,
J ¼ 6.4 Hz, 2H, H-30), 1.49 (m, 2H, H-40), 1.44 (t, J ¼ 6.4 Hz, 3H,
H-140). 13C NMR: 177.5 (C-4), 152.0 (C-2), 142.1 (C-20), 140.4 (C-8a),
d
132.1 (C-7), 126.8 (C-4a), 126.8 (C-5), 123.5 (C-10), 123.2 (C-6), 115.5