3660
J. M. Kim et al. / Bioorg. Med. Chem. 10 (2002) 3649–3661
1
Compound 33. H NMR(CDCl ) d 1.27 (dd, J=3.6,
2H), 3.56 (q, J=4.0 Hz, 2H), 3.87 (s, 6H), 5.06 (s, 2H),
5.93 (s, 2H), 6.70 (dd, J=1.2, 8.0 Hz, 1H), 6.74 (d,
J=7.6 Hz, 1H), 6.82 (d, J=1.2 Hz, 1H), 7.02 (s, 2H),
7.28–7.36 (m, 3H), 7.47 (d, J=7.2 Hz, 2H), 8.10 (bs,
1H); MALDI calcd for C32H39N3O6=561.67,
obsd=560.20. Anal. calcd for C39N3O62HCl: C, 60.57;
H, 6.51; N, 6.62; Found: C, 60.46; H, 6.73; N, 6.65.
3
12.2 Hz, 2H), 1.31 (dd, J=3.6, 12.2 Hz, 2H), 1.64 (bs,
1H), 1.75 (quintet, J=6.0 Hz, 2H), 1.82 (d, J=12.8 Hz,
2H), 2.02 (t, J=10.0 Hz, 2H), 2.40 (tt, J=4.0, 10.0 Hz,
1H), 2.83 (t, J=5.2 Hz, 2H), 2.90 (d, J=12.0 Hz, 2H), 2.95
(d, J=5.2 Hz, 2H), 3.55 (q, J=5.6 Hz, 2H), 3.78 (s, 6H),
4.18 (t, J=7.6 Hz, 1H), 5.05 (s, 2H), 7.00 (s, 2H), 7.16–7.37
(m, 13H), 7.48 (d, J=6.8 Hz, 2H), 8.11 (bs, 1H); MALDI
calcd for C38H45N3O4=607.78, obsd=605.57.
1
Compound 39. H NMR(CDCl ) d 1.36 (dd, J=3.6,
3
12.2 Hz, 2H), 1.41 (dd, J=3.6, 12.2 Hz, 2H), 1.76
(quintet, J=5.6 Hz, 2H), 1.87 (d, J=11.6 Hz, 2H), 1.98
(t, J=11.6 Hz, 2H), 2.35 (s, 3H), 2.46 (tt, J=4.0, 10.0
Hz, 1H), 2.84 (t, J=6.0 Hz, 2H), 2.85 (d, J=11.6 Hz,
2H), 3.43 (s, 2H), 3.55 (q, J=6.0 Hz, 2H), 3.86 (s, 6H),
5.06 (s, 2H), 7.03 (s, 2H), 7.08 (t, J=7.2 Hz, 2H), 7.11
(s, 1H), 7.20 (t, J=7.2 Hz, 1H), 7.27–7.39 (m, 3H), 7.47
(d, J=6.8 Hz, 2H), 8.12 (bs, 1H); HRMS-FAB (m/z)
[M+H]+ calcd for C32H42N3O4 532.3163; found
532.3175.
1
Compound 34. H NMR(CDCl ) d 1.39 (dd, J=3.6,
3
12.2 Hz, 2H), 1.43 (dd, J=3.6, 12.2 Hz, 2H), 1.79
(quintet, J=6.0 Hz, 2H), 1.81 (bs, 1H), 1.93 (d, J=12.0
Hz, 2H), 2.04 (t, J=12.0 Hz, 2H), 2.45 (tt, J=4.0, 10.0
Hz, 1H), 2.57 (dd, J=6.0, 10.8 Hz, 2H), 2.79 (dd,
J=6.0, 10.8 Hz, 2H), 2.85 (t, J=6.0 Hz, 2H), 2.96 (d,
J=11.6 Hz, 2H), 3.56 (q, J=5.6 Hz, 2H), 3.86 (s, 6H),
5.05 (s, 2H), 7.02 (s, 2H), 7.19 (d, J=5.6 Hz, 2H), 7.27–
7.36 (m, 3H), 7.47 (d, J=6.8 Hz, 2H), 7.98 (bs, 1H);
HRMS-FAB (m/z) [M+H]+ calcd for C32H42N3O4
532.3176; found 532.3174.
1
Compound 40. H NMR(CDCl ) d 1.36 (dd, J=3.6,
3
12.2 Hz, 2H), 1.41 (dd, J=3.6, 12.2 Hz, 2H), 1.76
(quintet, J=6.0 Hz, 2H), 1.87 (d, J=12.4 Hz, 2H), 2.02
(t, J=12.0 Hz, 2H), 2.44 (tt, J=4.0, 10.0 Hz, 1H), 2.58
(t, J=6.0 Hz, 2H), 2.83 (t, J=6.4 Hz, 2H), 2.90 (d,
J=12.0 Hz, 2H), 3.55 (t, J=6.0 Hz, 2H), 3.56 (t, J=6.0
Hz, 2H), 3.86 (s, 6H), 4.53 (s, 2H), 5.05 (s, 2H), 7.01 (s,
2H), 7.28–7.36 (m, 8H), 7.47 (d, J=6.8 Hz, 2H), 7.99
(bs, 1H); HRMS-FAB (m/z) [M+H]+ calcd for
C33H44N3O5, 562.3272; found, 562.3281.
1
Compound 35. H NMR(CDCl ) d 1.35 (dd, J=3.6,
3
12.2 Hz, 2H), 1.39 (dd, J=3.6, 12.2 Hz, 2H), 1.75
(quintet, J=5.6 Hz, 2H), 1.86 (d, J=12.4 Hz, 2H), 2.03
(t, J=11.6 Hz, 2H), 2.43 (tt, i=4.0, 10.0 Hz, 1H), 2.82
(t, J=5.6 Hz, 2H), 2.94 (d, J=11.6 Hz, 2H), 3.55 (q,
J=5.6 Hz, 2H), 3.68 (s, 2H), 3.76 (s, 3H), 3.81 (s, 6H),
5.05 (s, 2H), 6.99 (s, 1H), 7.01 (s, 2H), 7.12 (dt, J=1.2,
6.8 Hz, 1H), 7.23 (dt, J=1.2, 6.8 Hz, 1H), 7.29–7.36 (m,
4H), 7.47 (d, J=8.4 Hz, 2H), 7.68 (d, J=7.6 Hz, 1H),
8.05 (bs, 1H); HRMS-FAB (m/z) [M+H]+ calcd for
C34H43N4O4 571.3295; found 571.3284.
1
Compound 41. H NMR(CDCl ) d 1.32 (dd, J=3.6,
3
12.2 Hz, 2H), 1.36 (dd, J=3.6, 12.2 Hz, 2H), 1.76
(quintet, J=6.0 Hz, 2H), 1.87 (d, J=12.0 Hz, 2H), 1.97
(t, J=11.6 Hz, 2H), 2.00 (bs, 1H), 2.46 (tt, J=4.0, 10.0 Hz,
1H), 2.79 (d, J=11.6 Hz, 2H), 2.82 (t, J=6.0 Hz, 2H), 3.45
(s, 1H), 3.48 (s, 2H), 3.55 (q, J=5.6 Hz, 2H), 3.86 (s, 6H),
5.06 (s, 2H), 6.00 (dd, J=2.8, 5.6 Hz, 1H), 6.11 (dd, J=2.8,
5.6 Hz, 1H), 6.74 (dd, J=2.8, 4.2 Hz, 1H), 7.02 (s, 2H),
7.29–7.36 (m, 3H), 7.47 (d, J=8.4 Hz, 2H), 7.93 (bs, 1H);
MALDI calcd for C29H38N4O4=506.64, obsd=504.45.
1
Compound 36. H NMR(CDCl ) d 1.39 (dd, J=3.6,
3
12.2 Hz, 2H), 1.43 (dd, J=3.6, 12.2 Hz, 2H), 1.75
(quintet, J=6.0 Hz, 2H), 1.87 (d, J=11.2 Hz, 2H), 2.04
(t, J=11.6 Hz, 2H), 2.45 (tt, J=4.0, 10.0 Hz, 1H), 2.84
(t, J=5.6 Hz, 2H), 2.88 (d, J=11.6 Hz, 2H), 3.56 (q,
J=6.4 Hz, 2H), 3.63 (s, 2H), 3.87 (s, 6H), 5.06 (s, 2H),
7.03 (s, 2H), 7.28–7.36 (m, 3H), 7.45–7.49 (m, 5H), 7.71
(s, 1H), 7.79–7.84 (m, 3H), 8.14 (bs, 1H); MALDI calcd
for C35H41N3O4=567.72, obsd=565.43. Anal. calcd for
C35H41N3O42HCl: C, 65,62; H, 6.76; N, 6.56; Found: C,
65.48; H, 6.60; N, 6.52.
1
Compound 42. H NMR(CDCl ) d 1.33 (dd, J=3.6,
3
12.2 Hz, 2H), 1.38 (dd, J=3.6, 12.4 Hz, 2H), 1.73
(quintet, J=6.0 Hz, 2H), 1.86 (d, J=12.4 Hz, 2H), 1.93
(t, J=11.6 Hz, 2H), 2.22 (s, 3H), 2.41 (tt, J=4.0, 10.4
Hz, 1H), 2.76 (d, J=12. 0 Hz, 2H), 2.80 (t, J=6.0 Hz,
2H), 3.52 (q, J=6.4 Hz, 2H), 3.83 (s, 6H), 5.03 (s, 2H),
7.00 (s, 2H), 7.25–7.36 (m, 3H), 7.45 (d, J=8.0 Hz, 2H),
7.97 (t, J=4.8 Hz, 1H); HRMS-FAB (m/z) [M+H]+
calcd for C25H36N3O4 442.2706; found 442.2728.
1
Compound 37. H NMR(CDCl ) d 1.38 (dd, J=3.0,
3
12.0 Hz, 2H), 1.42 (dd, J=3.0, 12.0 Hz, 2H), 1.71 (bs,
1H), 1.76 (t, J=5.6 Hz, 2H), 1.89 (d, J=10.4 Hz, 2H),
2.05 (t, J=11.2 Hz, 2H), 2.46 (tt, J=4.0, 10.0 Hz, 1H),
2.86 (t, J=5.6 Hz, 2H), 2.89 (d, J=11.6 Hz, 2H), 3.51
(s, 2H), 3.57 (q, J=6.0 Hz, 2H), 3.88 (s, 6H), 5.06 (s,
2H), 7.03 (s, 2H), 7.27–7.38 (m, 6H), 7.44–7.48 (m, 4H),
7.54–7.61 (m, 4H), 8.12 (bs, 1H); MALDI calcd for
C37H43N3O4=593.76, obsd=591.36. Anal. calcd for
C37H43N3O42HCl: C, 66.80; H, 6.80; N, 6.30; Found: C,
66.80; H, 7.00; N, 6.42.
1
Compound 43. H NMR(CDCl ) d 1.35 (dd, J=3.6,
3
12.0 Hz, 2H), 1.39 (dd, J=3.6, 12.0 Hz, 2H), 1.79
(quintet, J=5.6 Hz, 2H), 1.89 (d, J=12.0 Hz, 2H), 2.06
(t, J=11.6 Hz, 2H), 2.49 (tt, J=4.0, 10.8 Hz, 1H), 2.82
(t, J=6.0 Hz, 2H), 2.89 (d, J=11.6 Hz, 2H), 2.97 (d,
J=7.2 Hz, 2H), 3.54 (q, J=6.0 Hz, 2H), 4.20 (t, J=7.6
Hz, 1H), 5.09 (s, 2H), 6.97 (d, J=8.8 Hz, 2H), 7.16–7.20
(m, 2H), 7.24–7.30 (m, 8H), 7.35–7.46 (m, 5H), 7.80 (d,
J=8.8 Hz, 2H), 8.28 (t, J=4.8 Hz, 1H); HRMS-FAB
(m/z) [M+H]+ calcd for C36H42N3O2 548.3269; found
548.3277.
1
Compound 38. H NMR(CDCl ) d 1.35 (dd, J=3.6,
3
12.2 Hz, 2H), 1.39 (dd, J=3.6, 12.2 Hz, 2H), 1.77
(quintet, J=6.0 Hz, 2H), 1.87 (d, J=12.0 Hz, 2H), 1.95
(t, J=12.0 Hz, 2H), 2.46 (tt, J=4.0, 10.0 Hz, 1H), 2.81
(d, J=12.0 Hz, 2H), 2.85 (t, J=5.6 Hz, 2H), 3.37 (s,