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(1H, d, J=2.5 Hz, C-4-H), 6.76 (1H, dd, J=8.7 Hz and
J=2.5 Hz, C-2-H), 7.19 (1H, d, J=8.7 Hz, C-1-H),
7.31–7.44 (5H, m, C6H5) and 10.63 (1H, s, NH); 13C
NMR (DMSO-d6) d 16.2 (q), 25.1, 25.2, 29.2, 32.4, 32.7
(all t), 37.8, 40.3 (all d), 40.5 (s), 41.9 (d), 68.9 (t), 112.2,
114.1, 126.0, 127.3 (2ꢁ), 127.4, 128.2 (2ꢁ) (all d), 131.5,
137.0, 137.1, 156.0, 172.1 and 178.9 (all s). MS m/z
(FAB+) 390.2 [58, (M+H)+], 91.1 [100, (CH2Ar)+].
HRMS m/z (FAB+) calcd for C25H28NO3: 390.2069.
Found: 390.2059. Anal. calcd for C25H27NO3: C, 77.09;
H, 6.99; N, 3.60. Found: C, 76.90; H, 6.99; N, 3.73.
137.0, 156.7, 171.3 and 178.2 (all s). MS m/z (FAB+)
446.3 [97, (M+H)+], 91.0 [100, (CH2Ar)+]. HRMS m/z
(FAB+) calcd for C29H36NO3: 446.2695. Found:
446.2691. Anal. calcd for C29H35NO3: C, 78.17; H, 7.92;
N, 3.14. Found: C, 77.80; H, 7.89; N, 3.13.
3-Benzyloxy-N-pentyl-16,17-seco-estra-1,3,5(10)-triene-
16,17-imide (14). White solid (550 mg, 93%). For ana-
lysis, a sample was recrystallized from EtOH to give
colorless needles: mp 104–107 ꢀC. IR (KBr) nmax 3100–
3000, 2960–2870, 1720, 1660, 1610–1500 cmꢂ1 1H
.
NMR (CDCl3) d 0.89 (3H, t, J=7.2 Hz, C-50-H3), 1.16
(3H, s, C-18-H3), 1.20–2.98 (17H, m), 2.83–2.89 (2H, m,
C-6-H2), 3.66–3.82 (2H, m, N–CH2), 5.03 (2H, s,
OCH2Ar), 6.72 (1H, d, J=2.7 Hz, C-4-H), 6.80 (1H, dd,
J=8.6 Hz and J=2.7 Hz, C-2-H), 7.21 (1H, d, J=8.6
Hz, C-1-H) and 7.30–7.44 (5H, m, C6H5); 13C NMR
(CDCl3) d 14.1, 16.6 (all q), 22.5, 25.6, 25.8, 27.7, 29.2,
29.7, 33.7, 33.8 (all t), 38.7 (d), 40.1 (t), 40.3 (d), 41.5 (s),
42.5 (d), 70.0 (t), 112.5, 114.5, 126.1, 127.3 (2ꢁ), 127.8,
128.4 (2ꢁ) (all d), 131.5, 137.0, 137.2, 156.8, 171.4 and
178.4 (all s). MS m/z (FAB+) 460.2 [78, (M+H)+],
91.1 [100, (CH2Ar)+]. HRMS m/z (FAB+) calcd for
C30H38NO3: 460.2852. Found: 460.2845. Anal. calcd for
C30H37NO3: C, 78.40; H, 8.11; N, 3.05. Found: C,
78.20; H, 8.08; N, 3.01.
3-Benzyloxy-N-ethyl-16,17-seco-estra-1,3,5(10)-triene-
16,17-imide (11). White solid (502 mg, 94%): mp 93–
95 ꢀC. IR (KBr) nmax 2975–2865, 1715, 1665, 1605–1500
0
cmꢂ1. H NMR (CDCl3) 1.11 (3H, t, J=7.2 Hz, C-2 -
H3), 1.16 (3H, s, C-18-H3), 1.31–2.98 (11H, m), 2.85–
2.90 (2H, m, C-6-H2), 3.81 (2H, m, N–CH2), 5.04 (2H,
s, OCH2Ar), 6.72 (1H, d, J=2.7 Hz, C-4-H), 6.81 (1H,
dd, J=8.6 Hz and J=2.7 Hz, C-2-H), 7.22 (1H, d,
J=8.6 Hz, C-1-H) and 7.30–7.44 (5H, m, C6H5); 13C
NMR (CDCl3) d 13.1, 16.4 (all q), 25.5, 25.7, 29.6, 33.5,
33.6, 35.0 (all t), 38.5, 40.2 (all d), 41.3 (s), 42.4 (d), 69.8
(t), 112.4, 114.4, 126.0, 127.1 (2ꢁ), 127.6, 128.3 (2ꢁ) (all
d), 131.4, 136.9, 137.0, 156.7, 171.1 and 178.0 (all s). MS
m/z (FAB+) 418.3 [90, (M+H)+], 91.0 [100,
(CH2Ar)+]. HRMS m/z (FAB+) calcd for C27H31NO3:
417.2304. Found: 417.2306.
1
3-Benzyloxy-N-hexyl-16,17-seco-estra-1,3,5(10)-triene-
16,17-imide (15). White solid (575 mg, 94%). For ana-
lysis, a sample was recrystallized from EtOH to give
white needles: mp 108–111 ꢀC. IR (KBr) nmax 2960–
2860, 1720, 1665, 1615–1500 cmꢂ1. 1H NMR (CDCl3) d
0.87 (3H, t, J=6.6 Hz, C-60-H3), 1.16 (3H, s, C-18-H3),
1.28–2.98 (19H, m), 2.84–2.89 (2H, m, C-6-H2), 3.74
(2H, m, N–CH2), 5.04 (2H, s, OCH2Ar), 6.72 (1H, d,
J=2.7 Hz, C-4-H), 6.81 (1H, dd, J=8.6 Hz and J=2.7
Hz, C-2-H), 7.22 (1H, d, J=8.6 Hz, C-1-H) and 7.29–
7.44 (5H, m, C6H5); 13C NMR (CDCl3) d 14.1, 16.6 (all
q), 22.6, 25.6, 25.8, 26.7, 28.0, 29.8, 31.6, 33.7, 33.8 (all
t), 38.7 (d), 40.1 (t), 40.4 (d), 41.5 (s), 42.5 (d), 70.0 (t),
112.6, 114.5, 126.1, 127.3 (2ꢁ), 127.8, 128.4 (2ꢁ) (all d),
131.6, 137.0, 137.2, 156.8, 171.4 and 178.4 (all s). MS m/
z (FAB+) 474.3 [68, (M+H)+], 91.0 [100, (CH2Ar)+].
HRMS m/z (FAB+) calcd for C31H40NO3: 474.3008.
Found: 473.2988. Anal. calcd for C31H39NO3: C, 78.61;
H, 8.30; N, 2.96. Found: C, 78.10; H, 8.16; N, 2.98.
3-Benzyloxy-N-propyl-16,17-seco-estra-1,3,5(10)-triene-
16,17-imide (12). White solid (524 mg, 94%). For ana-
lysis, a sample was recrystallized from EtOH to give
white crystals: mp 95–98 ꢀC. IR (KBr) nmax 3035, 2960–
2870, 1720, 1660, 1610–1500 cmꢂ1. 1H NMR (CDCl3) d
0.89 (3H, t, J=7.6 Hz, C-30-H3), 1.16 (3H, s, C-18-H3),
1.32–2.98 (13H, m), 2.83–2.88 (2H, m, C-6-H2), 3.64–
3.80 (2H, m, N–CH2), 5.03 (2H, s, OCH2Ar), 6.72 (1H,
d, J=2.7 Hz, C-4-H), 6.80 (1H, dd, J=8.6 Hz and
J=2.7 Hz, C-2-H), 7.21 (1H, d, J=8.6 Hz, C-1-H) and
7.30–7.44 (5H, m, C6H5); 13C NMR (CDCl3) d 11.4,
16.6 (all q), 21.3, 25.6, 25.8, 29.8, 33.7, 33.8 (all t), 38.7,
40.4 (all d), 41.5 (s), 41.6 (t), 42.5 (d), 70.0 (t), 112.6,
114.5, 126.1, 127.3 (2ꢁ), 127.8, 128.4 (2ꢁ) (all d), 131.5,
137.0, 137.2, 156.8, 171.5 and 178.4 (all s). MS m/z
(FAB+) 432.4 [88, (M+H)+], 91.1 [100, (CH2Ar)+].
HRMS m/z (FAB+) calcd for C28H34NO3: 432.2539.
Found: 432.2522. Anal. calcd for C28H33NO3: C, 77.93;
H, 7.71; N, 3.25. Found: C, 77.60; H, 7.68; N, 3.26.
3-Benzyloxy-N-(40-bromobutyl)-16,17-seco-estra-1,3,5(10)-
triene-16,17-imide (16). White solid (569 mg, 84%). For
analysis, a sample was recrystallized from EtOH to give
white crystals: mp 113–116 ꢀC. IR (KBr) nmax 2935–
2860, 1720, 1670, 1605–1500 cmꢂ1. 1H NMR (CDCl3) d
1.17 (3H, s, C-18-H3), 1.30–3.00 (15H, m), 2.84–2.90
(2H, m, C-6-H2), 3.42 (2H, t, J=6.8 Hz, C-40-H2), 3.79
(2H, m, N–CH2), 5.04 (2H, s, OCH2Ar), 6.72 (1H, d,
J=2.7 Hz, C-4-H), 6.81 (1H, dd, J=8.6 Hz and J=2.7
Hz, C-2-H), 7.21 (1H, d, J=8.6 Hz, C-1-H) and 7.30–
7.45 (5H, m, C6H5); 13C NMR (CDCl3) 17.0 (q), 25.9,
26.1, 27.1, 30.1, 30.5, 33.5, 33.9, 34.1 (all t), 39.0 (d),
39.3 (t), 40.6 (d), 41.8 (s), 42.8 (d), 70.3 (t), 112.9, 114.8,
126.4, 127.6 (2ꢁ), 128.1, 128.8 (2ꢁ) (all d), 131.8, 137.3,
137.5, 157.1, 171.8 and 178.8 (all s). MS m/z (FAB+)
524.1 [42, (M+H)+], 91.0 [100, (CH2Ar)+]. HRMS m/z
3-Benzyloxy-N-butyl-16,17-seco-estra-1,3,5(10)-triene-
16,17-imide (13). White solid (513 mg, 90%). For ana-
lysis, a sample was recrystallized from EtOH to give
white needles: mp 100–103 ꢀC. IR (KBr) nmax 2960–
1
2870, 1720, 1665, 1615–1500 cmꢂ1. H NMR (CDCl3)
0.92 (3H, t, J=7.2 Hz, C-40-H3), 1.16 (3H, s, C-18-H3),
1.28–2.99 (15H, m), 2.84–2.89 (2H, m, C-6-H2), 3.75
(2H, m, N–CH2), 5.04 (2H, s, OCH2Ar), 6.72 (1H, d,
J=2.5 Hz, C-4-H), 6.81 (1H, dd, J=8.6 Hz and J=2.5
Hz, C-2-H), 7.22 (1H, d, J=8.6 Hz, C-1-H) and 7.29–
7.45 (5H, m, C6H5); 13C NMR (CDCl3) d 13.8, 16.5 (all
q), 20.1, 25.5, 25.7, 29.6, 30.0, 33.5, 33.7 (all t), 38.5 (d),
39.7 (t), 40.2 (d), 41.3 (s), 42.4 (d), 69.8 (t), 112.4, 114.4,
126.0, 127.1 (2ꢁ), 127.6, 128.3 (2ꢁ) (all d), 131.4, 136.9,