A. Pouilhe`s et al. / Tetrahedron Letters 42 (2001) 8297–8299
9. (a) Diker, K.; Do¨e´ de Maindreville, M.; Le´vy, J. Tetra-
8299
CH2×3; 2.14–1.86, 1H, m, and 1.74–1.22, 7H, CH2×4. 13
C
NMR (62.5 MHz, CDCl3): 155.7, C7; 136.4, C8a; 135.0,
C9a; 122.2, C4b; 118.4, C5; 107.7, C6; 106.9, C4a; 95.5, C8;
57.8, C3; 55.9, C1; 54.6, NCH2×2; 43.6, NCH2; 32.0, CH2;
26.1, C4; 24.2, CH2; 22. 4, CH2×2. Compound 7h 1H
NMR: 8.48, 1H, N9H; 7.43, 1H, s, 7.29, 1H, d, 7.11, 1H,
d, C8-H, C6-H and C5-H; 4.16–3.88, 1H, m, C1-H; 3.53–
3.28, 1H, m and 3.12–2.82, 1H, m, C3H2; 2.73–2.12, 9H,
m, N2-H, C4-H2, NCH2×3; 2.05–1.84, 1H, m, and 1.80–
1.38, 7H, m, CH2×4. 13C NMR (62.5 MHz, CDCl3):
137.4, C8a; 136.4, C4b; 126.6, C9a; 121.7, C5; 119.2, C6;
114.0, C7; 113.7, C8; 58.0, C3; 56.0, C1; 54.7, NCH2×2;
43.9, NCH2; 32.7, CH2; 26.1, C4; 24.2, CH2; 22.4, CH2×
2.
hedron Lett. 1995, 36, 2497; (b) Le´tinois, S.; Dumur,
J.-C.; He´nin, F.; Muzart, J. Tetrahedron Lett. 1998, 39,
2327.
10. Selected data: 1H NMR (200 MHz, l ppm, TMS=0,
CDCl3): compound 7b 1H NMR: 12, 1H, N9-H; 7.48, 1H,
d, 7.34, 1H, d, 6.98–7.18, 2H, m, C5-H, C8-H, C6-H and
C7-H; 4.13–3.98, 1H, m, C1-H; 3.58–3.30, 1H, m, C3-H;
3.11–2.92, 1H, m, C3-H; 2.88–2.21, 9H, m, C4-H2,
NCH2×3, N2-H; 2.08–1.91, 1H, m, and 1.88–1.46, 7H, m,
CH2×4. 13C NMR (50 MHz, CDCl3): 136.6, C8a; 135.6,
C4b; 127.6, C9a; 120.8, C6; 118.6, C5; 118.0, C7; 111.0, C8;
107.2, C4a; 58, C3; 55.9, C1; 54.2, NCH2×2; 44.0, NCH2;
32.5, CH2; 25.9, C4; 24.1, CH2; 22.6, CH2×2. Compound
7e 1H NMR: 10.90, 1H, N9-H; 7.51, 1H, dd, 7.29, 1H,
dd, 7.12, 2H, dt, C5-H, C8-H, C6-H and C7-H; 4.10, 1H,
t, C1-H; 3.37 and 3.01, 2H, m, C3-H2; 2.92–2.68, 3H, m,
N2-H and C4-H2; 2.61, 1H, m, and 2.42, 1H, m, CH2;
2.26, 6H, s, N(CH3)2; 1.91, 2H, m, CH2. 13C NMR (50
MHz, CDCl3): 135.9 and 135.7, C4b and C8a; 127.5, C9a;
121.0, 118.7, 118.0 and 111.1, C5, C6, C7 and C8; 107.6,
C4a; 58.0, C4; 54.6, C1, 45.2, N(CH3)2; 43.3, C3; 32.8,
CH2; 22.4, CH2. Compound 7g 1H NMR: 8.71, 1H, s,
N9-H; 7.34, 1H, d, 6.83, 1H, s and 6.71, 1H, s, C6-H,
C8-H, C5-H; 4.12–3.95, 1H, m, C1-H; 3.79, 3H, s, OCH3;
3.42–2.72, 2H, m, C3-H2; 2.72–2.10, 9H, m, N2-H, C4-H2,
11. L1210 murine leukaemia cells were grown in RPMI 1640
medium supplemented with 10% foetal calf serum, 2 mM
L
-glutamine, 100 units/mL penicillin, 100 mg/mL strepto-
mycin and 10 mM HEPES buffer. Cells were exposed to
graduated concentrations of the compounds. After incu-
bation for 48 h at 37°C, cell proliferation was measured
by MTT essay (Alley, M. C; Scudiero, A.; Monks, M. L.;
Cserwinski, M. J.; Fine, D. L.; Abott, B. J.; Mayo, J. G.;
Shoemaker, R. H.; Boyd, M. R. Cancer Res., 1988, 48,
589.). Results are expressed as IC50.
12. Other manzamine type alkaloids devoided of b-carboline
unit also showed significant cytotoxicity, see Ref. 1c.