J. Xie, C. T. Seto / Bioorg. Med. Chem. 13 (2005) 2981–2991
2989
2H), 6.82 (t, J = 7.3 Hz, 1H), 7.08 (d, J = 8.9 Hz, 2H),
7.13–7.21 (m, 3H), 7.64 (dd, J = 8.6, 2.3 Hz, 1H), 7.81
(d, J = 8.8 Hz, 2H), 7.99 (d, J = 8.8 Hz, 2H), 8.32 (d,
J = 2.3 Hz, 1H), 8.41 (s, 1H), 8.88 (s, 1H); 13C NMR
(75 MHz, CDCl3) d 28.5, 67.7, 67.9, 85.1, 85.2, 113.7,
115.2, 115.4, 115.6, 118.2, 120.7, 126.6, 127.3, 127.4,
129.5, 129.9, 132.8, 133.0, 133.3, 134.7, 145.4, 161.9,
162.1, 164.1, 165.7, 166.0, 185.6; HRMS-ESI (M+Na+)
calcd for C40H41N3NaO10 746.2690, found 746.2660.
preparation of compound 12 (pink solid, 55 mg,
0.112 mmol, 63%). H NMR (300 MHz, CDCl3) d 1.64
1
(s, 9H), 2.27 (s, 3H), 4.31 (br s, 2H), 4.69 (s, 2H),
6.76–6.94 (m, 4H), 7.06–7.13 (m, 3H), 7.37–7.43 (m,
2H), 8.02 (d, J = 8.9 Hz, 2H), 8.20 (s, 1H); 13C NMR
(75 MHz, CDCl3) d 21.8, 28.5, 67.9, 85.2, 106.6, 110.5,
110.9, 115.4, 123.8, 126.8, 127.3, 127.6, 129.3, 133.0,
137.0, 138.6, 139.3, 139.6, 150.2, 162.0, 164.0, 165.6,
185.6; HRMS-ESI (MꢀHꢀ) calcd for C27H27N2O5S
491.1641, found 491.1630.
5.9. Compound 13
5.13. Compound 15
Compound 12 (60 mg, 0.083 mmol) was stirred with
5 mL of 80% TFA in methylene chloride for 30 min.
The solvent was then removed to afford 45 mg
Compound 15 was prepared from 55 mg of compound
14 by procedures analogous to the preparation of com-
pound 13 (gray powder, 48 mg, 0.11 mmol, 98%). H
1
1
(0.076 mmol, 91%) of compound 13 as gray solid. H
NMR (300 MHz, CDCl3) d 4.92 (s, 2H), 5.46 (s, 2H),
7.13–7.27 (m, 5H), 7.53–7.62 (m, 7H), 7.87–7.96 (m,
4H), 8.22 (s, 1H), 10.36 (s, 1H); 13C NMR (75 MHz,
CDCl3) d 63.3, 68.0, 110.1, 111.9, 116.2, 118.8, 126.0,
126.3, 127.5, 130.3, 130.9, 132.8 (two overlapping
peaks), 133.0, 135.1, 135.4, 140.4, 149.8, 163.4, 164.1,
166.6, 167.2, 167.3, 187.9, 188.0; HRMS-ESI (MꢀHꢀ)
calcd for C32H22N3O9 592.1356, found 592.1335.
NMR (300 MHz, DMSO-d6) d 2.21 (s, 3H), 4.87 (s,
2H), 6.79–6.94 (m, 4H), 7.11–7.27 (m, 5H), 7.93 (d,
J = 8.8 Hz, 2H), 10.1 (s, 1H); 13C NMR (75 MHz,
DMSO-d6) d 21.8, 67.9, 106.1, 107.6, 109.5, 116.2,
123.9, 125.9, 126.9, 127.2, 129.7, 132.8, 137.9, 138.5,
139.1, 141.8, 151.5, 164.1, 166.6, 167.3, 188.0; HRMS-
ESI (MꢀHꢀ) calcd for C23H19N2O5S 435.1015, found
435.1025.
5.10. Compound 10
5.14. Compound 16
Compound 10 was prepared from compound 3 and dia-
mine D52 by procedures analogous to the preparation of
compound 12 (dark red powder, 73 mg, 0.099 mmol,
56%). 1H NMR (300 MHz, CDCl3) d 1.62 (s, 18H),
4.65 (s, 2H), 4.70 (s, 2H), 7.04 (d, J = 8.5 Hz, 2H),
7.18 (d, J = 8.7 Hz, 2H), 7.50 (t, J = 7.4 Hz, 2H), 7.61
(t, J = 7.2 Hz, 1H), 7.70 (d, J = 8.6 Hz, 1H), 7.77 (d,
J = 7.3 Hz, 2H), 7.97 (m, 5H), 8.40 (s, 1H), 8.68 (d,
J = 8.9 Hz, 1H), 11.6 (s, 1H); 13C NMR (75 MHz,
CDCl3) d 28.5, 67.7 (two overlapping peaks), 85.1,
85.3, 115.4, 115.5, 122.6, 124.9, 125.6, 126.2, 127.2,
127.4, 128.8, 130.5, 132.1, 132.9, 133.0, 133.4, 136.2,
138.3, 162.0, 162.3, 164.0, 164.2, 165.8, 166.6, 185.6,
185.8, 198.7; HRMS-ESI (M+Na+) calcd for
C41H40N2NaO11 759.2530, found 759.2520.
Compound 16 was prepared from compound 3 and
36 mg of diamine D62 by procedures analogous to the
preparation of compound 12 (white solid, 66 mg,
1
0.091 mmol, 51%). H NMR (300 MHz, CDCl3) d 1.62
(s, 18H), 4.68 (s, 4H), 6.98 (d, J = 8.6 Hz, 4H), 7.06 (d,
J = 8.5 Hz, 4H), 7.55 (d, J = 8.7 Hz, 4H), 7.98 (d,
J = 8.5 Hz, 4H), 8.34 (s, 2H); 13C NMR (75 MHz,
CDCl3) d 28.5, 67.8, 85.3, 115.4, 119.7, 122.6, 127.4,
132.5, 133.0, 154.6, 162.2, 164.1, 165.6, 185.7; HRMS-
ESI (M+Na+) calcd for C40H40N2NaO11 747.2530,
found 747.2534.
5.15. Compound 17
Compound 17 was prepared from 66 mg of compound
16 by procedures analogous to the preparation of com-
pound 13 (white solid, 52 mg, 0.085 mmol, 93%). 1H
NMR (300 MHz, DMSO-d6) d 4.87 (s, 4H), 6.98 (d,
J = 8.9 Hz, 4H), 7.20 (d, J = 8.8 Hz, 4H), 7.62 (d,
J = 8.9 Hz, 4H), 7.94 (d, J = 8.8 Hz, 4H), 10.2 (s, 2H);
13C NMR (75 MHz, DMSO-d6) d 67.8, 116.2, 119.6,
122.3, 126.0, 132.8, 134.7, 153.7, 164.0, 166.4, 167.3,
188.0; HRMS-ESI (MꢀHꢀ) calcd for C32H23N2O11
611.1302, found 611.1310.
5.11. Compound 11
Compound 11 was prepared from 73 mg of compound
10 by procedures analogous to the preparation of com-
pound 13 (gray powder, 60 mg, 0.096 mmol, 97%). H
1
NMR (300 MHz, DMSO-d6) d 4.70 (s, 2H), 4.85 (s,
2H), 7.16 (dd, J = 9.4 Hz, 4H), 7.52 (t, J = 7.5 Hz,
2H), 7.65 (t, J = 7.2 Hz, 1H), 7.72 (d, J = 7.3 Hz, 2H),
7.80 (d, J = 1.9 Hz, 1H), 7.89–7.96 (m, 6H), 10.4 (s,
1H), 10.7 (s, 1H); 13C NMR (75 MHz, DMSO-d6) d
67.8, 116.2 (two overlapping peaks), 122.8, 124.4,
124.6, 126.0, 126.2, 129.3, 129.8, 130.6, 132.8, 133.0,
133.7, 135.3, 138.0, 163.4, 164.0, 166.8, 167.2, 167.3,
187.9, 196.9; HRMS-ESI (MꢀHꢀ) calcd for
C33H23N2O11 623.1302, found 623.1325.
5.16. Compound 18
Compound 18 was prepared from compound 3 and
50 mg of diamine D70 by procedures analogous to the
preparation of compound 12 (brown powder, 72 mg,
1
0.089 mmol, 50%). H NMR (300 MHz, CDCl3) d 1.66
(s, 18H), 4.40 (dd, J = 22.7, 15.1 Hz, 4H), 6.32 (d,
J = 8.9 Hz, 4H), 7.02 (d, J = 8.4 Hz, 2H), 7.24
(t, J = 7.6 Hz, 2H), 7.44 (t, J = 7.5 Hz, 2H), 7.76 (d,
J = 8.9 Hz, 4H), 7.93 (d, J = 8.1 Hz, 2H), 8.02 (s, 2H),
8.08 (d, J = 9.1 Hz, 2H), 8.70 (d, J = 9.0 Hz, 2H); 13C
5.12. Compound 14
Compound 14 was prepared from compound 3 and
41 mg of diamine D54 by procedures analogous to the