Effect of indole ring substitution and variation of electronic substituent effects.
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|---|---|---|---|---|---|---|---|---|
| Compound # | Y | X | Binding affinity | Activity | ||||
| Ki (nM) | EC50 (nM) | |||||||
| SST1 | SST2A | SST3 | SST4 | SST5 | SST4 | |||
| 214 | — | — | — | >10 000 | — | 717.3 | — | 1036 |
| 181 | 6-F | H | 1825 | >10 000 | >10 000 | 3.0 | >10 000 | 2.8 |
| 191 | 6-F | 3,4-Cl2 | 872.6 | 1104 | 1557 | 1.1 | >10 000 | 1.0 |
| 193 | 6-F | 3,5-Cl2 | — | 4862 | — | 1.7 | — | 2.2 |
| 188 | 6-F | 3-Cl | — | 1734 | — | 0.5 | — | 0.8 |
| 184 | 6-F | 4-F | 468.0 | 3969 | >10 000 | 0.9 | >10 000 | 3.2 |
| 194 | 6-F | 3-Br | 263.5 | 2080 | 2733 | 1.0 | >10 000 | 0.3 |
| 196 | 6-F | 3-CF3 | 543.6 | 3278 | 1613 | 0.7 | 6526 | 0.2 |
| 206 | 6-F | 3-CN | — | 5884 | — | 6.9 | — | 7.2 |
| 199 | 6-F | 2-OCH3 | — | 5115 | — | 0.9 | — | 0.2 |
| 201 | 6-F | 3-OCH3 | 971.1 | 5605 | 5404 | 0.6 | >10 000 | 0.7 |
| 203 | 6-F | 4-OCH3 | 1080 | 5304 | >10 000 | 5.1 | >10 000 | 6.7 |
| 208 | 6-F | 3-SO2CH3 | 443.2 | >10 000 | >10 000 | 0.7 | >10 000 | 2.5 |
| 210 | 6-F | 4-SO2CH3 | — | >10 000 | — | 80.8 | — | 846.9 |
| 211 | — | — | 4336 | >10 000 | >10 000 | 57.1 | >10 000 | 77.7 |
| 212 | — | — | 97.8 | 639.7 | 1736 | 0.7 | 9335 | 0.7 |
| 182 | 5-OCH3 | H | 1716 | 7103 | >10 000 | 3.1 | >10 000 | 6.0 |
| 185 | 5-OCH3 | 4-F | 1032 | 5434 | >10 000 | 2.8 | >10 000 | 6.0 |
| 197 | 5-OCH3 | 3-CF3 | 365.3 | 1693 | 1129 | 1.8 | >10 000 | 1.0 |
| 204 | 5-OCH3 | 4-OCH3 | 1011 | >10 000 | >10 000 | 3.3 | >10 000 | 5.6 |