A. P. Misra et al. / Bioorg. Med. Chem. 9 (2001) 2763–2772
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Compound 7. Yield: 56%; mp 186 ꢁC; IR (KBr):
1758 cmꢀ1 (>C¼O), 1642 cmꢀ1 (>C¼O); 1H NMR
(200 MHz CDCl3): d 7.38 (dd, 2H, J=6.8, 2 Hz, Ar–H),
7.16 (s, 1H, H-3), 7.06 (s, 1H, NH exchangeable), 6.85
(dd, 2H, J=6.8, 2 Hz, Ar–H), 5.29–4.89 (m, 6H, H-10–
H-40, H-1and H-7), 4.32 (dd, 1H, J=12, 4 Hz, H-60),
4.14 (dd, 1H, J=12, 2 Hz, H-60), 3.79 (s, 3H, OCH3),
3.75 (m, 1H, H-50), 3.12 (m, 1H, H-5), 2.29 (m, 1H, H-
6), 2.19 (m, 1H, H-9), 2.10, 2.04, 2.03, 2.01, 1.92 (s, 3H
each, COCH3), 1.99 (m, 1H, H-8), 1.95 (m, 1H, H6).
1.04, (d, 3H, J=6.8 Hz, H-10). MS (FAB): m/z 692
(M++1). Anal. calcd for C33H41NO15: C, 57.30; H,
5.93; N, 2.02. Found: C, 57.33; H, 5.72; N, 2.22; [a]
ꢀ64.23 (c 0.26 in methanol).
55.80; H, 6.2; N, 2.01%; [a] ꢀ102.74 (c 0.25 in methanol).
Compound 11. Yield: 60%; mp 75 ꢁC; IR (KBr):
3428 cmꢀ1 (NH), 1752 cmꢀ1, 1664 cmꢀ1 (>C¼O); 1H
NMR (200 MHz, CDCl3): d 7.14 (s, 1H, H-3), 5.89 (m,
1H, NH exchangeable), 5.23–4.83 (m, 6H, H-10–H-40,
H-1and H-7), 4.25 (dd, 1H, J=12, 4 Hz, H-60), 4.11–
4.03 (m, 3H, H-60 and NCH2), 3.76 (s, 3H, OCH3), 3.76
(m, 1H, H-50), 3.01 (m, 1H, H-5), 2.28 (m, 1H, H-6),
2.24 (m, 1H, H-9), 2.20 (m, 1H, H-8), 2.09, 2.04, 2.03,
1.99, 1.91 (s, 3H each, COCH3), 1.85 (m, 1H, H-6), 1.03
(d, 3H, J=6.8, H-10). MS (ES): m/z 624 (M++1).
Anal. calcd for C29H37NO14.3=2H2O: C, 53.53; H, 6.15;
N, 2.15. Found: C, 53.26; H, 5.93; N, 2.19%.
Compound 8. Yield: 40%; mp 67 ꢁC; IR (KBr):
1752 cmꢀ1, 1642 cmꢀ1 (>C¼O); 1H NMR (200 MHz,
CDCl3); d 7.43–7.22 (m, 5H, Ar–H), 7.15 (s, 1H, H-3),
5.77 (d, 1H, J=7.2 Hz, NH exchangeable), 5.29 (d, 1H,
J=2.4 Hz, H-1), 5.26–4.94 (m, 5H, H-10–H-40 and H-7),
4.50 (dd, 1H, J=12, 4 Hz, H-60), 4.20 (dd, 1H, J=12,
2 Hz, H-60), 3.92 (s, 3H, OCH3), 3.86 (m, 2H, H-50 and
CHCH2), 3.35 (dd, 1H, J=13.8, 6 Hz, CHCH2), 3.25
(dd, 1H, J=13.8, 6 Hz, CHCH2), 3.08 (m, 1H, H-5),
2.36 (m, 1H, H-6), 2.24, 2.17, 2.15, 2.13, 2.10 (s, 3H
each, COCH3), 2.07 (m, 1H, H-9), 2.05 (m, 1H, H-8),
1.57 (m, 1H, H-6), 1.21 (d, 3H, J=6.8 Hz, H-10). MS
(FAB): m/z 748 (M++1), 770 (M++Na). Anal. calcd
for C36H45NO16: C, 57.83; H, 6.02; N, 1.87. Found: C,
57.77; H, 6.26; N, 1.88%; [a] ꢀ99.2 (c 0.25 in metha-
nol).
Compound 12. Yield: 81%; mp 80 ꢁC; IR (KBr):
1
1752 cmꢀ1, 1662 cmꢀ1 (>C¼O); H NMR (200 MHz,
CDCl3): d 7.18 (m, 10H, Ar–H), 7.0 (s, 1H, H-3), 6.19
(d, 1H, J=7.5 Hz, NH exchangeable), 5.22–4.83 (m,
6H, H-10-H-40, H-1and H-7), 4.30 (dd, 1H, J=12, 4 Hz,
H-60), 4.16 (dd, 1H, J=12, 2 Hz, H-60), 3.95 (m, 1H,
CHCH2), 3.7 (m, 1H, H-50), 3.29 (m, 2H, NCH2), 2.8
(m, 1H, H-5), 2.30 (m, 2H, CH2CH), 2.24 (m, 1H, H-6),
2.09, 2.04, 2.03, 2.0, 1.88 (s, 3H each, COCH3), 1.94 (m,
1H, H-9), 1.92 (m, 1H, H-8), 1.81 (m, 1H, H-6), 1.01 (d,
3H, J=6.8 Hz, H-10). MS (ES): m/z 780 (M++1), 802
(M++Na). Anal. calcd for C41H49NO14: C, 63.15; H,
6.29; N, 1.79. Found: C, 63.29; H, 6.37; N, 2.08%; [a]
ꢀ73.96 (c 0.26 in methanol).
Compound 13. Yield: 88%; mp 69 ꢁC; IR (KBr):
1
1754 cmꢀ1, 1654 cmꢀ1 (>C¼O); H NMR (200 MHz,
Compound 9. Yield: 53.6%; mp 105 ꢁC; IR (KBr):
3486 cmꢀ1 (NH), 1750 cmꢀ1, 1640 cmꢀ1 (>C¼O); 1H
CDCl3): d 7.09 (s, 1H, H-3), 5.24 (m, 1H, NH
exchangeable), 5.18–4.82 (m, 6H, H-10-H-40, H-1and H-
NMR (200 MHz, CDCl3):
d
8.29 (bs, 1H, NH
7), 4.31(dd, H1 ,
J=12, 4 Hz, H-60), 4.13 (dd, 1H,
exchangeable), 7.53 (d, 1H, J=8, H-400), 7.37 (d, 1H,
J=8 Hz, H-700), 7–7.14 (m, 3H, H-3, H-200 and H-600),
6.99 (m, 1H, H-500), 5.72 (d, 1H, J=7.4 Hz, H-1), 5.22–
4.77 (m, 5H, H-20–H-40 H-1and H-7), 4.30 (dd, 1H,
J=12, 4, H-60), 4.17 (m, 1H, CHCOOCH3), 4.11 (dd,
1H, J=12, 2 Hz, H-60), 3.74 (s, 3H, OCH3), 3.70 (m,
1H, H-50), 3.34 (m, 2H, CH2CHCOOCH3), 2.80 (m, 1H,
H-5), 2.08 (m, 1H, H-6), 2.08 (m, 1H, H-9), 2.03, 2.01,
2.0, 1.96, 1.89 (s, 3H each, COCH3), 1.85 (m, 1H, H-8),
1.83 (m, 1H, H-6), 0.96 (d, 3H, J=6.8 Hz, H-10). MS
(FAB): m/z 787 (M++1). Anal. calcd for C38H46N2O16,
H2O: C, 56.71; H, 5.97; N, 3.48. Found C, 56.70; H,
6.03; N, 3.58%; [a] ꢀ80.78 (c 0.25 in methanol).
Compound 10. Yield: 62.7%; mp 185 ꢁC; IR (KBr):
3482 cmꢀ1 (OH), 1754 cmꢀ1, 1662 cmꢀ1 (>C¼O); 1H
NMR (200 MHz, CDCl3): d 7.03 (s, 1H, H-3), 6.95 (d,
2H, J=8.4 Hz, Ar–H), 6.77 (d, 2H, J=8.4 Hz, Ar–H),
6.1 (bs, 1H, OH exchangeable), 5.66 (d, 1H, J=7.3 Hz,
NH exchangeable), 5.22–4.78 (m, 6H, H-10, H-40, H-1
and H-7), 4.25 (dd, 1H, J=12, 4 Hz, H-60), 4.16 (m, 1H,
CHCH2), 4.15 (dd, 1H, J=12, 2 Hz, H-60), 3.77 (s, 3H,
OCH3), 3.77 (m, 1H, H-50), 3.2 (dd, 1H, J=13, 5 Hz,
CHCH2), 2.9 (d, 1H, CHCH2), 2.88 (m, 1H, H-5), 2.15
(m, 2H, H-6, H-9), 2.09, 2.05, 2.04, 2.03, 2.0 (s, 3H each,
COCH3), 2.03 (m, 2H, H-8, H-6), 0.99 (d, 3H, J=6.8 Hz,
H-10). MS (ES): m/z 764 (M++1). Anal. calcd for
C36H46NO17.1=2H2O: C, 55.95; H, 6.08; N, 1 .8. Found: C,
J=12, 2 Hz, H-60), 3.75 (m, 1H, H-50), 3.31(m, 2H,
NCH2), 2.96 (m, 1H, H-5), 2.2 (m, 1H, H-6), 2.09, 2.04,
2.03, 2.0, 1.92 (s, 3H each, COCH3), 1.81 (m, 1H, H-9),
1.75 (m, 1H, H-8), 1.67 (m, 1H, H-6), 1.39 (m, 4H,
(CH2)2), 1.02 (d, 3H, J=6.8, H-10), 0.96 (t, 3H, J=7,
CH2CH3); MS (ES): m/z 642 (M++1); Analysis calcd
for C30H43NO14: C, 56.10; H, 6.70; N, 2.18. Found: C,
55.87; H, 6.71; N, 2.38%; [a] ꢀ58.07 (c 0.26 in metha-
nol).
Compound 14. Yield: 83%; mp: 105 ꢁC; IR (KBr):
1752 cmꢀ1 (>C¼O), 1674 cmꢀ1 (>C¼O); 1H NMR
(200 MHz, CDCl3): d 7.31 (m, 5H, Ar–H), 7.13 (s, 1H,
H-3), 5.65 (m, 1H, NH exchangeable), 5.23–4.82 (m,
6H, H-10-H-40, H-1and H-7), 4.48 (m, 2H, NCH 2), 4.28
(dd, 1H, J=12, 4 Hz, H-60), 4.10 (dd, 1H, J=12 and
2 Hz, H-60), 3.70 (m, 1H, H-50), 2.9 (m, 1H, H-5), 2.17
(m, 1H, H-9), 2.09 (m, 1H, H-8), 2.17, 2.09, 2.02, 2.01,
1.99 (s, 3H each, COCH3), 1.02 (d, 3H, J=6.8 Hz, H-
10). MS (ES): m/z 676 (M++1), 698 (M++Na). Anal.
calcd for C33H41NO14; C, 58.66; H, 6.07; N, 2.07.
Found: C, 58.66; H, 5.93; N, 2.10%; [a] ꢀ60.76 (c 0.26
in methanol).
Compound 15. Yield: 61%; mp: 101 ꢁC; IR (KBr):
1742 cmꢀ1 (>C¼O), 1642 cmꢀ1 (>C¼O); 1H NMR
(200 MHz, CDCl3): d 7.13 (s, 1H, H-3), 5.88 (d, 1H,
J=8.5 Hz, NH exchangeable), 5.23–4.83 (m, 6H, H-10-