Med Chem Res
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1425, 1141. H NMR (CDCl3, 500 MHz): 5.23 (1H, s, H-
12), 4.04–4.01 (2H, m, CH2), 3.20 (1H, dd, J = 15 Hz, 10
Hz, H-3), 2.48–2.36 (4H, brm, CH2), 2.29 (2H, s, CH2),
2.23 (1H, d, J = 10 Hz, H-18), 1.64–1.61 (m, CH2),
1.58–1.56 (m, CH2), 1.07 (CH3, s, H-27), 0.99 (CH3, s, H-
25), 0.94 (CH3, s, H-26), 0.93 (CH3, s, H-24), 0.88 (CH3, s,
H-23), 0.85 (CH3, d, J = 10 Hz, H-30), 0.78 (CH3, d, J = 16
Hz, H-29). 13C NMR (CDCl3, 125 MHz): 177.6 (C-28),
138.3 (C-13), 125.5 (C-12), 79.1 (C-3), 62.7 (CH2), 55.3
(C-5), 55.1 (CH2), 53.2 (C-18), 52.8 (CH2), 48.1 (C-17),
47.6 (C-9), 46.0 (CH2), 42.1 (C-14), 39.6 (C-8), 39.1 (C-
19), 38.9 (C-1), 38.8 (C-4), 38.6 (C-20), 37.0 (C-10), 36.8
(C-22), 33.1 (C-7), 30.7 (C-21), 29.7 (CH2), 28.2 (C-23),
28.0 (C-15), 27.2 (C-3), 24.3 (C-16), 23.6 (C-11), 23.3 (C-
27), 23.37 (CH2), 21.2 (C-30), 18.3 (C-6), 17.3 (C-26), 17.0
(C-29), 15.7 (C-25), 15.5 (C-24).
18.2 (C-6), 16.8 (C-26), 16.7 (C-29), 15.5 (C-25), 15.1
(C-24).
(4-(Piperidin-1-yl) butyl) 3-hydroxy-urs-12-en-28-oate
(3h) Yield: 46 %; colorless oil; ESI-MS: 596 [M+H]+; IR
(KBr, cm−1) v: 3498, 3236, 2934, 2802, 1710, 1454, 1093.
1H NMR (CDCl3, 500 MHz): 5.23 (1H, s, H-12), 3.99 (2H,
t, J = 5 Hz, CH2), 3.20 (1H, dd, J = 10 Hz, 5 Hz, H-3), 2.39
(4H, brs, CH2), 2.32 (2H, t, J = 7.5 Hz, CH2), 2.23 (1H, d, J
= 10 Hz, H-18), 1.65–1.61 (m, CH2), 1.55–1.50 (m, CH2),
1.07 (CH3, s, H-27), 0.98 (CH3, s, H-25), 0.94 (CH3, s, H-
26), 0.93 (CH3, s, H-24), 0.91 (CH3, s, H-23), 0.86 (CH3, d,
J = 10 Hz, H-30), 0.77 (CH3, d, J = 15 Hz, H-29). 13C NMR
(CDCl3, 125 MHz): 177.6 (C-28), 138.2 (C-13), 125.6 (C-
12), 79.0 (C-3), 64.2 (CH2), 59.0 (CH2), 55.3 (C-5), 54.9
(C-18), 52.9 (CH2), 48.1 (C-17), 47.6 (C-9), 42.1 (C-14),
39.6 (C-8), 39.1 (C-19), 38.9 (C-1), 38.8 (C-4), 38.6 (C-20),
37.0 (C-10), 36.8 (C-22), 33.1 (C-7), 30.7 (C-21), 28.2 (C-
23), 28.0 (C-15), 27.3 (C-3), 26.8 (CH2), 25.9 (CH2), 24.4
(C-16), 24.2 (CH2), 23.6 (C-11), 23.5 (CH2), 23.3 (C-27),
21.2 (C-30), 18.3 (C-6), 17.2 (C-26), 17.1 (C-29), 15.7 (C-
25), 15.5 (C-24).
(3-(Pyrrolidin-1-yl) propyl) 3-hydroxy-urs-12-en-28-oate
(3f) Yield: 53 %; colorless oil; ESI-MS: 568 [M+H]+; IR
(KBr, cm−1) v: 3431, 2945, 2868, 1728, 1458, 1045. H
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NMR (CDCl3, 500 MHz): 5.21 (1H, s, H-12), 4.07–3.99
(2H, m, CH2), 3.20 (1H, dd, J = 10 Hz, 10 Hz, H-3), 2.76
(2H, brs, CH2), 2.66–2.63 (4H, m, CH2), 2.19 (1H, d, J =
10 Hz, H-18), 1.65–1.62 (m, CH2), 1.59–1.57 (m, CH2),
1.05 (CH3, s, H-27), 0.96 (CH3, s, H-25), 0.92 (CH3, s, H-
26), 0.91 (CH3, s, H-24), 0.88 (CH3, s, H-23), 0.83 (CH3, d,
J = 6 Hz, H-30), 0.76 (CH3, d, J = 20 Hz, H-29). 13C NMR
(CDCl3, 125 MHz): 177.5 (C-28), 138.4 (C-13), 125.5 (C-
12), 79.0 (C-3), 62.2 (CH2), 55.2 (C-5), 54.0 (CH2), 53.1
(C-18), 52.8 (CH2), 48.1 (C-17), 47.5 (C-9), 42.1 (C-14),
39.6 (C-8), 39.1 (C-19), 38.9 (C-1), 38.8 (C-4), 38.6 (C-20),
37.0 (C-10), 36.8 (C-22), 33.0 (C-7), 30.7 (C-21), 29.7
(CH2), 28.2 (C-23), 28.0 (C-15), 27.2 (C-2), 24.3 (C-16),
23.6 (C-11), 23.4 (C-27), 23.35 (CH2), 21.2 (C-30), 18.3
(C-6), 17.3 (C-26), 17.0 (C-29), 15.7 (C-25), 15.5 (C-24).
(4-(Pyrrolidin-1-yl) butyl) 3-hydroxy-urs-12-en-28-oate
(3i) Yield: 41.6 %; colorless oil; ESI-MS: 582 [M+H]+; IR
(KBr, cm−1) v: 3530, 2946, 2858, 1721, 1456, 1378, 1045.
1H NMR (CDCl3, 500 MHz): 5.24 (1H, s, H-12), 4.01–3.98
(2H, m, CH2), 3.19 (1H, dd, J = 10 Hz, 10 Hz, H-3), 2.52
(4H, brs, CH2), 2.47 (2H, t, J = 7.5 Hz, CH2), 2.21 (1H, d, J
= 10 Hz, H-18), 1.80–1.76 (2H, m, CH2), 1.65–1.62 (2H,
m, CH2), 1.36–1.39 (2H, m, CH2), 1.07 (CH3, s, H-27),
0.98 (CH3, s, H-25), 0.94 (CH3, s, H-26), 0.93 (CH3, s, H-
24), 0.91 (CH3, s, H-23), 0.86 (CH3, d, J = 10 Hz, H-30),
0.77 (CH3, d, J = 10 Hz, H-29). 13C NMR (CDCl3, 125
MHz): 177.6 (C-28), 138.2 (C-13), 125.6 (C-12), 79.0 (C-
3), 64.1 (CH2), 56.1 (CH2), 55.3 (C-5), 54.2 (CH2), 52.9 (C-
18), 48.1 (C-17), 47.6 (C-9), 42.1 (C-14), 39.6 (C-8), 39.1
(C-19), 38.9 (C-1), 38.8 (C-4), 38.7 (C-20), 37.0 (C-10),
36.8 (C-22), 33.1 (C-7), 30.7 (C-21), 28.2 (C-23), 28.0 (C-
15), 27.3 (C-2), 26.8 (CH2), 25.5 (CH2), 24.2 (C-16), 23.6
(C-11), 23.5 (CH2), 23.4 (C-27), 21.2 (C-30), 18.3 (C-6),
17.2 (C-26), 17.1 (C-29), 15.7 (C-25), 15.5 (C-24).
(3-Morpholinopropyl) 3-hydroxy-urs-12-en-28-oate (3g)
Yield: 51 %; colorless oil; ESI-MS: 584 [M+H]+; IR (KBr,
cm−1) v: 3458, 2949, 2868, 1714, 1454, 1384, 1118. H
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NMR (CD3COCD3-d6, 500 MHz): 5.23 (1H, t, J = 5 Hz, H-
12), 4.08–3.99 (2H, m, CH2), 3.60 (4H, t, J = 5 Hz, CH2),
3.15 (1H, dd, J = 10 Hz, 10 Hz, H-3), 2.85 (2H, brs, CH2),
2.45–2.33 (6H, m, CH2), 2.24 (1H, d, J = 10 Hz, H-18),
1.12 (CH3, s, H-27), 0.98 (CH3, s, H-25), 0.96 (CH3, s, H-
26), 0.95 (CH3, s, H-24,), 0.89 (CH3, s, H-23), 0.87 (CH3,
d, J = 10 Hz, H-30), 0.79 (CH3, d, J = 5 Hz, H-29).13C
NMR (CD3COCD3-d6, 500 MHz): 176.5 (C-28), 138.4 (C-
13), 125.5 (C-12), 78.3 (C-3), 66.6 (CH2), 61.8 (CH2), 55.3
(CH2), 55.2 (C-5), 53.8 (CH2), 53.0 (C-18), 47.8 (C-17),
47.6 (C-9), 41.9 (C-14), 39.6 (C-8), 39.0 (C-19), 38.9 (C-1),
38.7 (C-4), 38.7 (C-20), 36.9 (C-10), 36.7 (C-22), 33.0 (C-
7), 30.4 (C-21), 27.9 (C-23), 27.8 (C-15), 27.2 (C-2), 25.6
(CH2), 24.1 (C-16), 23.2 (C-11), 23.2 (C-27), 20.6 (C-30),
(4-Morpholinobutyl) 3-hydroxy-urs-12-en-28-oate (3j)
Yield: 51 %; colorless oil; ESI-MS: 598 [M+H]+; IR (KBr,
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cm−1) v: 3560, 3375, 2949, 2854, 1701, 1465, 1118. H
NMR (CDCl3, 500 MHz): 5.28 (1H, s, H-12), 4.01–3.98
(2H, m, CH2), 3.72 (4H, t, J = 5 Hz, CH2), 3.20 (1H, dd, J
= 10 Hz, 10 Hz, H-3), 2.43 (4H, brs, CH2), 2.34 (2H, t, J =
7.5 Hz, CH2), 2.23 (1H, d, J = 10 Hz, H-18), 1.07 (CH3, s,
H-27), 0.98 (CH3, s, H-25), 0.94 (CH3, s, H-26), 0.93 (CH3,
s, H-24), 0.91 (CH3, s, H-23), 0.86 (CH3, d, J = 10 Hz, H-
30), 0.77 (CH3, d, J = 15 Hz, H-29). 13C NMR (CDCl3,
125 MHz):177.6 (C-28), 138.2 (C-13), 125.6 (C-12), 79.0