Scheme 1
Figure 1
Figure 2
Figure 3
Figure 4
Glide docking scores of substituted chromone-2-carboxamides 5a–n at the active site of ER-α (PDB ID: 7KBS) and ER-β (PDB ID: 2FSZ)
| Compounds | Structure | Glide docking scores of ER-α (7KBS) | Glide docking scores of ER-β (2FSZ) |
|---|---|---|---|
| 5a |
| −5.25 | −5.17 |
| 5b |
| −5.22 | −6.16 |
| 5c |
| −6.80 | −4.24 |
| 5d |
| −6.02 | −6.16 |
| 5e |
| −6.12 | −7.54 |
| 5f |
| −7.10 | −7.09 |
| 5g |
| −6.44 | −6.16 |
| 5h |
| −7.10 | −7.05 |
| 5i |
| −4.76 | −5.12 |
| 5j |
| −4.82 | −5.11 |
| 5k |
| −1.485 | −2.70 |
| 5l |
| −4.71 | −6.68 |
| 5m |
| −4.88 | −6.87 |
| 5n |
| −4.83 | −5.84 |
| Tamoxifen | −8.02 | −10.55 |
In vitro antiproliferative activities of substituted chromone-2-carboxamides 5a–n
| Compounds | Structure | Yield (%) | M.P. (°C) | IC50 (µM) | ||
|---|---|---|---|---|---|---|
| MCF-7 | MDA-MB-231 | ISHIKAWA | ||||
| 5a |
| 90 | 196–197 | >100 | >100 | >100 |
| 5b |
| 49 | 225* | 35.8 | 93.1 | >100 |
| 5c |
| 27 | 270* | > 100 | >100 | >100 |
| 5d |
| 82 | 271–272 | 38.2 | >100 | 36.2 |
| 5e |
| 26 | 295–296 | >100 | >100 | >100 |
| 5f |
| 40 | 300* | 87.8 | >100 | >100 |
| 5g |
| 69 | 300* | 25.7 | 48.3 | 25.7 |
| 5h |
| 70 | 300* | >100 | 43.6 | >100 |
| 5i |
| 35 | 270* | >100 | >100 | >100 |
| 5j |
| 37 | 290* | >100 | >100 | >100 |
| 5k |
| 34 | 250* | 32.8 | 81.6 | >100 |
| 5l |
| 50 | 135–136 | >100 | >100 | >100 |
| 5m |
| 40 | 270* | >100 | >100 | >100 |
| 5n |
| 44 | 225* | >100 | >100 | >100 |
| Tamoxifen | — | — | 12.7 | 22.8 | 18.1 | |