Table 7.
Anticancer activity of all known trigonoliimines and structurally related alkaloids.a
| Entry | Compound | HeLa (μM) |
U-937 (μM) |
|---|---|---|---|
| 1 | (−)-1 | >50 | 44 ± 9 |
| 2 | (±)-1 | >50 | 21.3 ± 4.5 |
| 3 | (−)-2 | >50 | 34.6 ± 7.1 |
| 4 | (−)-3 | >50 | 20.3 ± 3.1 |
| 5 | (±)-3 | >100 | 29.6 ± 9.5 |
| 6 | (−)-4 | >50 | >35 |
| 7 | (−)-11•CD3CO2D | 29.7 ± 3.1 | 10.9 ± 0.2 |
| 8 | (−)-12•CD3CO2D | >100 | 38.6 ± 9.5 |
| 9 | (±)-23 | >50 | 19.2 ± 4.4 |
| 10 | (±)-24 | >30 | 10.3 ± 3.0 |
| 11 | (±)-24•CF3CO2D | 8.6 ± 1.8 | 0.73 ± 0.05 |
| 12 | (+)-52 | >100 | 35.6 ± 9.2 |
| 13 | 68 | 3.6 ± 1.1 | 7.9 ± 0.5 |
| 14 | (±)-69 | 13.6 ± 6.3 | 22.8 ± 2.2 |
| 15 | (+)-69b | 35.8 ± 8.6 | >50 |
a
72-hour IC50 values in HeLa (human cervical cancer) or U-937 (human lymphoma) cell lines as monitored by SRB (HeLa) or MTS (U-937). Error is standard deviation of the mean, n=3. SRB: sulforhodamine B; MTS: 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium.
b
43% ee.