2668
X. Qian et al. / Bioorg. Med. Chem. Lett. 14 (2004) 2665–2668
þ
J. Am. Chem. Soc. 2002, 124, 13972–13973; (e) Teulade-
J 7.98, 2-H), 8.59 (1H, d, J 8.12, 5-H); m=z 374 (M ,
1.62%), 304 (23.30), 303 (29.64), 71 (29.58), 58 (100), 56
Fichou, M.; Perrin, D.; Boutorine, A.; Polverari, D.;
Vigneron, J.; Lehn, J.; Sun, J. S.; Garestier, T.; Helene,
C. J. Am. Chem. Soc. 2001, 123, 9283–9292; (f) Hwu, J. R.;
Lu, K. L.; Yu, S. F.; Yu, L. J.; Kumaresan, S.; Lin, K. J.;
Tsay, S. C. Photochem. Photobiol. 2002, 75, 457–461; (g)
Rogers, J. E.; Le, T. P.; Kelly, L. A. Photochem. Photobiol.
ꢀ
1
(9.81), 43 (12.49); mmax (KBr)/cm 2950, 2870, 1695, 1660,
1560 and 1380; C22 S requires C, 70.57; H, 4.85; N,
7.48; found C, 70.46; H, 4.98; N, 7.35. A2: Mp 286–287 ꢁC.
(500 MHz; CDCl ; Me Si) 2.80 (2H, t, J 5.96 and 6.00,
NCH ), 2.89 (4H, s, NHCH (cyclo)), 3.14 (4H, s, NCH
(cyclo)), 4.32 (2H, t, J 6.08 and 5.88, CONCH ), 7.38–7.46
18 2 2
H N O
d
H
3
4
2
2
2
2
001, 73, 223–229; (h) Zhang, Y.; Yang, S.; Liu, C.; Dai,
X.; Cao, W.; Xu, J.; Li, Y. New J. Chem. 2002, 26, 617–620;
i) Hurley, A. L.; Maddox, M. P., III; Scott, T. L.; Flood,
2
(3H, m, 8-H, 9-H, 10-H), 7.54 (1H, d, J 8.06, 7-H), 8.19–
8.25 (2H, m, 1-H, 6-H), 8.42 (1H, d, J 8.01, 2-H), 8.62 (1H,
d, J 8.18, 5-H); m=z 415 (M , 5.45%), 373 (39.42), 330
(35.98), 303 (27.95), 99 (100.0), 70 (27.95), 56 (42.09), 42
(
þ
M. R.; Mohler, D. L. Org. Lett. 2001, 3, 2761–2764; (j)
Tsai, F. Y.; Lin, S. B.; Tsay, S. C.; Lin, W. C.; Hsieh, C. L.;
Chuang, S. H.; Kan, L. S.; Hwu, J. R. Tetrahedron Lett.
ꢀ1
(21.07); mmax (KBr)/cm 3410, 2970, 2840, 1690, 1640 and
1330; C24 S requires C, 69.38; H, 5.09; N, 10.11;
found C, 69.56; H, 5.23; N, 9.96. A3: Mp 202–203 ꢁC. d
(500 MHz; CDCl ; Me Si) 2.46 (8H, s, NCH , NCH ), 2.70
(2H, t, J 7.39 and 7.49, CH ), 4.25 (2H, t, J 7.24 and 7.24,
CONCH ), 7.40 (3H, m, 8-H, 9-H, 10-H), 7.49 (1H, d, J
7.98, 7-H), 8.20 (2H, m, 1-H, 6-H), 8.39 (1H, d, J 7.98, 2-
H), 8.59 (1H, d, J 8.10, 5-H). A4: Mp 185–186 ꢁC. d
(500 MHz; CDCl ; Me Si) 0.98 (3H, t, J 7.37 and 7.37,
CH ), 1.43–1.50 (2H, m, (Me)-CH ), 1.68–1.78 (2H, m,
(C )-CH ), 4.19 (2H, t, J 7.55 and 7.65, CONCH ), 7.38–
2
001, 42, 5733–5735; (k) Fernandez, M. J.; Grant, K. B.;
Herraiz, F.; Yang, X.; Lorente, A. Tetrahedron Lett. 2001,
2, 5701–5704; (l) Cornia, M.; Menozzi, M.; Ragg, E.;
21 3 2
H N O
H
4
3
4
3
2
Mazzini, S.; Scarafoni, A.; Zanardi, F.; Casiraghi, G.
Tetrahedron 2000, 56, 3977–3983; (m) Qian, X.; Huang, T.,
et al. J. Chem. Soc., Perkin. Trans. 2000, 2, 715; (n) Qian,
X.; Yao, W. Tetrahedron Lett. 2001, 42, 6175.
. (a) Brana, M.; Ramos, A. Curr. Med. Chem.: Anti-cancer
Agents 2001, 1, 237–255; (b) Rogers, J. E.; Weiss, S. J.;
Kelly, L. A. J. Am. Chem. Soc. 2000, 122, 427–436; (c)
Rogers, J. E.; Kelly, L. A. J. Am. Chem. Soc. 1999, 121,
2
2
H
2
3
4
3
2
2
H
5
2
2
7.43 (3H, m, 8-H, 9-H, 10-H), 7.52 (1H, d, J 7.98, 7-H),
8.20–8.27 (2H, m, 1-H, 6-H), 8.44 (1H, d, J 7.98, 2-H), 8.64
3854–3861; (d) Saito, I.; Takayama, M.; Sugiyama, H.;
Nakatani, K. J. Am. Chem. Soc. 1995, 117, 6406–6407; (e)
Qian, X.; Huang, T.-B.; Wei, D.-Z.; Zhu, D.-H.; Fan,
M.-C.; Yao, W. J. Chem. Soc., Perkin. Trans. 2000, 2, 715–
(1H, d, J 8.13, 5-H). A5: Mp 185–186 ꢁC. d
CDCl ; Me Si) 3.42 (6H, s, O-CH ), 4.39 (2H, d, J 5.74,
CONCH ), 4.93 (1H, t, J 5.68 and 5.68, CH), 7.38–7.44
H
(500 MHz;
3
4
3
2
7
18.
(3H, m, 8-H, 9-H, 10-H), 7.52 (1H, d, J 7.98, 7-H), 8.21
(2H, m, 1-H, 6-H), 8.44 (1H, d, J 7.99, 2-H), 8.64 (1H, d, J
8.13, 5-H); m=z 391 (M , 13.01%), 360 (23.51), 328 (16.07),
3
. Grayshan, P. H.; Kadhim, A. M.; Peters, A. T.
J. Heterocycl. Chem. 1974, 11, 33–38.
þ
4
. (a) Malviya, V. K.; Liu, P. Y.; Alberts, D. S.; Surwit, E. A.;
Craig, J. B.; Hanningan, E. V. Am. J. Clin. Oncol. 1992, 15,
303 (35.21), 232 (14.91), 75 (100), 57 (16.54), 43 (17.20); mmax
(KBr)/cm 2960, 2850, 1690, 1650 and 1330; C22H17NO S
4
ꢀ
1
4
1–44; (b) Rosell, R.; Carles, J.; Abad, A.; Ribelles, N.;
Barnadas, A.; Benavides, A.; Martin, M. Invest. New Drugs
992, 10, 171–175.
requires C, 67.50; H, 4.38; N, 3.58; found C, 67.24; H, 4.76;
N, 3.73.
6. de Silva, A. P.; Gunaratne, H. Q. N.; Habib-Jiwan, J.-L.;
McCoy, C. P.; Rice, T. E.; Soumillion, J.-P. Angew. Chem.,
Int. Ed. Engl. 1995, 34, 1728–1729.
1
5
. A1: Mp 212–213 ꢁC. d
1
CONCH
H
(500 MHz; CDCl
, NCH ), 4.42 (2H, t, J 6.78 and 6.65,
), 7.34–7.42 (m, 3H, 8-H, 9-H, 10-H), 7.48 (1H, d,
3 4
; Me Si) 1.20–
.34 (8H, m, NCH
3
2
2
7. Yao, W.; Qian, X. Dyes Pigments 2001, 48, 43–47.
8. Gupta, M.; Ali, R. J. Biochem. 1984, 95, 1253–1257.
J 7.99, 7-H), 8.14–8.20 (2H, m, 1-H, 6-H), 8.40 (1H, d,