(2H, both br.s, H-29), 6.89 (2H, m, H-2ꢅ, 6ꢅ), 6.98 (2H, m, H-3ꢅ, 5ꢅ) (for all compounds only characteristic proton resonances
are given). C H FN O .
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2 2
N-[3-Oxo-20(29)-lupen-28-oyl]-4-(3,4-dichlorophenyl)-piperazine (3). Yield 86.7%, white crystalline compound,
–1
99.2% purity (HPLC analysis), mp 182-183°C. IR spectrum (TIR, ꢄ, cm ): 2941, 1700 (C=O), 1626 (CONH), 1593, 1483,
1411, 1232, 1192, 1026, 882, 801.
PMR spectrum (600 MHz, CDCl , ꢀ, ppm): 0.93, 0.97, 1.01, 1.06 (15H, 4s, CH -23, 24, 25, 26, 27), 1.68 (3H, s,
3
3
CH -30), 2.39 (1H, m, H-2), 2.49 (1H, m, H-2), 2.91 (1H, m, H-13), 2.99 (1H, m, H-19), 3.11 (4H, m, H-3ꢁ, 3ꢁ, 5ꢁ, 5ꢁ), 3.76 (4H,
3
m, H-2ꢁ, 2ꢁ, 6ꢁ, 6ꢁ), 4.74 and 4.59 (2H, both br.s, H-29), 6.76 (1H, m, H-6ꢅ), 6.96 (1H, m, H-5ꢅ), 7.29 (1H, m, H-2ꢅ).
C H Cl N O .
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2 2 2
N-[3-Oxo-20(29)-lupen-28-oyl]-4-(4-nitrophenyl)-piperazine (4). Yield 78.5%, yellow crystalline compound, 99.2%
–1
purity (HPLC analysis), mp 197–198°C. IR spectrum (TIR, ꢄ, cm ): 2940, 1700 (C=O), 1626 (CONH), 1593, 1501, 1328,
1243, 1190, 1113, 1024, 879, 835.
PMR spectrum (600 MHz, CDCl , ꢀ, ppm, J/Hz): 0.93, 0.98, 0.99, 1.03, 1.08 (each 3H, s, CH -23, 24, 25, 26, 27),
3
3
1.69 (3H, s, CH -30), 2.39 (1H, m, H-2), 2.49 (1H, m, H-2), 2.90 (1H, m, H-13), 3.00 (1H, td, J = 10.8, J = 4.2, H-19), 3.41
3
1
2
(4H, m, H-3ꢁ, 3ꢁ, 5ꢁ, 5ꢁ), 3.80 (4H, m, H-2ꢁ, 2ꢁ, 6ꢁ, 6ꢁ), 4.74 and 4.60 (2H, both br.s, H-29), 6.85 (2H, d, J = 9.0, H-2ꢅ, 6ꢅ), 8.14
(2H, d, J = 9.0, H-3ꢅ, 5ꢅ). C H N O .
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3 4
N-[3-Oxo-20(29)-lupen-28-oyl]-4-(2-pyridyl)-piperazine (5). Yield 87.6%, white crystalline compound, 99.3%
–1
purity (HPLC analysis), mp 158–159°C. IR spectrum (TIR, ꢄ, cm ): 2938, 1703 (C=O), 1633 (CONH), 1592, 1478, 1435,
1243, 1189, 1020, 980, 882, 773.
PMR spectrum (600 MHz, CDCl , ꢀ, ppm, J/Hz): 0.93, 0.98, 1.01, 1.06 (15H, 4s, CH -23, 24, 25, 26, 27), 1.69 (3H,
3
3
s, CH -30), 2.39 (1H, m, H-2), 2.49 (1H, m, H-2), 2.94 (1H, m, H-13), 3.00 (1H, td, J = 10.8, J = 3.6, H-19), 3.51 (4H, m,
3
1
2
H-3ꢁ, 3ꢁ, 5ꢁ, 5ꢁ), 3.73 (4H, m, H-2ꢁ, 2ꢁ, 6ꢁ, 6ꢁ), 4.74 and 4.59 (2H, both br.s, H-29), 6.68 (2H, m, H-3ꢅ, 5ꢅ), 7.52 (1H, m, H-4ꢅ),
8.20 (1H, m, H-6ꢅ). C H N O .
39 57
3 2
N-[3-Oxo-20(29)-lupen-28-oyl]-4-(2-pyrimidyl)-piperazine (6). Yield 77.8%, white crystalline compound, 99.1%
–1
purity (HPLC analysis), mp 109–110°C. IR spectrum (TIR, ꢄ, cm ): 2940, 1703 (C=O), 1633 (CONH), 1584, 1448, 1257,
1188, 982, 879, 797.
PMR spectrum (600 MHz, CDCl , ꢀ, ppm, J/Hz): 0.93, 0.98, 1.02, 1.06 (15H, 4s, CH -23, 24, 25, 26, 27), 1.69 (3H,
3
3
s, CH -30), 2.39 (1H, m, H-2), 2.50 (1H, m, H-2), 2.94 (1H, m, H-13), 3.00 (1H, td, J = 10.8, J = 3.6, H-19), 3.69 (4H, m,
3
1
2
H-3ꢁ, 3ꢁ, 5ꢁ, 5ꢁ), 3.76 (4H, m, H-2ꢁ, 2ꢁ, 6ꢁ, 6ꢁ), 4.74 and 4.59 (2H, both br.s, H-29), 6.55 (1H, m, H-5ꢅ), 8.33 (2H, m, H-4ꢅ, 6ꢅ).
C H N O .
38 56
4 2
N-[3-Oxo-20(29)-lupen-28-oyl]-4-(4-trifluoromethylphenyl)-piperazine (7). Yield 74.9%, white crystalline
–1
compound, 98.9% purity (HPLC analysis), mp 229–230°C. IR spectrum (TIR, ꢄ, cm ): 2944, 1704 (C=O), 1626 (CONH),
1525, 1458, 1332, 1230, 1112, 1073, 1023, 885, 830.
PMR spectrum (600 MHz, CDCl , ꢀ, ppm, J/Hz): 0.93, 0.97, 0.98, 1.02, 1.06 (each 3H, s, CH -23, 24, 25, 26, 27),
3
3
1.69 (3H, s, CH -30), 2.39 (1H, m, H-2), 2.49 (1H, m, H-2), 2.92 (1H, m, H-13), 3.00 (1H, td, J = 11.4, J = 4.2, H-19), 3.24
3
1
2
(4H, m, H-3ꢁ, 3ꢁ, 5ꢁ, 5ꢁ), 3.78 (4H, m, H-2ꢁ, 2ꢁ, 6ꢁ, 6ꢁ), 4.74 and 4.60 (2H, both br.s, H-29), 6.94 (2H, d, J = 8.4, H-2ꢅ, 6ꢅ), 7.51
(2H, d, J = 8.4, H-3ꢅ, 5ꢅ). C H F N O .
41 57
3 2 2
ACKNOWLEDGMENT
The work was supported financially by Korea Forest Service [Forest Science & Technology Projects
(S120808L1201106)].
REFERENCES
1.
2.
3.
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