2280
S. J. Gregson et al. / Bioorg. Med. Chem. Lett. 13 (2003) 2277–2280
9. Thurston, D. E.; Bose, D. S.; Thompson, A. S.; Howard,
P. W.; Leoni, A.; Croker, S. J.; Jenkins, T. C.; Neidle, S.;
Hartley, J. A.; Hurley, L. H. J. Org. Chem. 1996, 61, 8141.
10. Gregson, S. J.; Howard, P. W.; Jenkins, T. C.; Kelland,
L. R.; Thurston, D. E. Chem. Commun. 1999, 797.
11. Gregson, S. J.; Howard, P. W.; Hartley, J. A.; Brooks,
N. A.; Adams, L. J.; Jenkins, T. C.; Kelland, L. R.; Thurston,
D. E. J. Med. Chem. 2001, 44, 737.
126.3, 119.6, 118.8, 117.9, 111.4, 109.9, 56.2, 54.0, 53.8, 46.7,
37.5, 37.2, 29.6, 24.2; MS (FAB), m/z (relative intensity) 514
(M+.+H, 97), 279 (43), 271 (19), 216 (23), 192 (53), 180 (100),
149 (21), 135 (17), 112 (28), 91 (59), 80(36), 73 (91), 57 (80);
IR (NUJOL) 3315 (br), 2924, 2854, 1682, 1624, 1598, 1511,
1455, 1378, 1246, 1214, 1128, 1071, 1010, 965, 872, 827, 722,
665 cmꢀ1; HRMS [M+H]+. calcd for C28H28N5O5 m/z
514.2090, Found (FAB) m/z 514.2096; [a]2D0=+624.0( c 0.03,
CHCl3).
12. Reddy, B. S. P.; Damayanthi, Y.; Reddy, B. S. N.; Lown,
J. W. Anti-Cancer Drug Des. 2000, 15, 225.
1
16. Data for 4b: H NMR (250MHz, CDCl3): d 8.28 (s, 1H),
13. Jones, P.; Villeneuve, G. B.; Fei, C. P.; DeMarte, J.; Hag-
garty, A. J.; Nwe, K. T.; Martin, D. A.; Lebuis, A. M.; Fin-
kelstein, J. M.; Gour-Salin, B. J.; Chan, T. H.; Leyland-Jones,
B. R. J. Med. Chem. 1998, 41, 3062.
7.86 (d, 1H, J=3.94 Hz), 7.69 (d, 1H, J=4.46 Hz), 7.53 (s, 1H),
7.50(s, 1H), 7.05 (s, 1H), 6.82 (s, 1H), 4.61–4.45 (m, 1H), 4.38–
4.21 (m, 1H), 3.95–3.78 (m, 9H), 3.60–3.48 (m, 2H), 3.34–3.00
(m, 4H), 2.37–2.18 (m, 2H), 2.10–1.78 (m, 2H); 13C NMR
(62.9MHz, CDCl3): d 167.2, 164.4, 162.5, 161.4, 151.9, 147.8,
146.1, 140.6, 140.4, 129.9, 127.1, 122.9, 118.9, 117.9, 111.5, 110.3,
109.8, 56.2, 56.1, 53.9, 53.6, 46.7, 37.6, 37.4, 29.6, 24.1; MS
(FAB), m/z (relative intensity) 544 (M+.+H., 100), 413 (83), 391
(89), 329 (54), 307 (91), 289 (81), 272 (77), 246 (56); IR (CHCl3)
3329 (br), 3011, 2930, 2867, 1725, 1691, 1602, 1511, 1454, 1434,
14. Gregson, S. J.; Howard, P. W.; Barcella, S.; Nakamya, A.;
Jenkins, T. C.; Kelland, L. R.; Thurston, D. E. Bioorg. Med.
Chem. Lett. 2000, 10, 1849.
1
15. Data for 4a: H NMR (400 MHz, CDCl3): d 7.89 (d, 1H,
J=8.24 Hz), 7.78–7.44 (m, 3H), 7.40–7.25 (m, 2H), 6.91 (s,
1H), 6.77 (s, 1H), 4.28–4.10(m, 1H), 3.89 and 3.85 (s ꢂ2, 6H),
3.83–3.60(m, 2H), 3.55–3.46 (m, 1H), 3.34–3.10(m, 4H),
2.36–1.60(m, 4H); 13C NMR (100.5 MHz, CDCl3): d 168.4,
164.8, 162.9, 161.5, 152.0, 147.8, 146.7, 141.2, 140.6, 131.2,
1387, 1343, 1264, 1215, 1128, 1073, 1019, 969, 874, 664 cmꢀ1
;
HRMS [M+H]+. calcd for C29H30N5O6 m/z 544.2196, Found
(FAB) m/z 544.2209; [a]2D3=+405.9 (c 0.10, CHCl3).