Table 2 In vitro COX-1 and COX-2 inhibition data, COX-2 selectivity index (SI), molecular volume, and calculated log P data of compounds 1, 5, 14, 7–12, 16–25, 28, 29, 32, and 33
From: In situ click chemistry generation of cyclooxygenase-2 inhibitors
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Compound | R 1 | X | COX-2 IC50 (µM) | COX-1 IC50(µM) | COX-2 SI | Cell COX-2 IC50 (µM) | V molecular [Å3] | log P |
7 | H | H | 0.9 | >100 | >111.1 | 3.0 | 327.9 | 6.03 |
8 | Cl | H | 0.16 | >100 | >625 | 4.0 | 341.4 | 6.58 |
9 | F | H | 0.14 | >100 | >714.2 | 2.0 | 332.8 | 6.18 |
10 | OCH3 | H | 15.2 | >100 | >6.5 | – | 353.4 | 5.90 |
11 | CH3 | H | 3.2 | >100 | >31.2 | 2.0 | 344.5 | 6.51 |
12 | CH2CH3 | H | 18 | >100 | >5.5 | – | 361.3 | 6.93 |
16 | H | SO2CH3 | 10 | >100 | >10 | – | 321.0 | 3.34 |
17 | Cl | SO2CH3 | 1.1 | >100 | >90.9 | 1.0 | 334.6 | 3.89 |
18 | F | SO2CH3 | 0.09 | >100 | >1,111.1 | 0.06 | 326.0 | 3.49 |
19 | OCH3 | SO2CH3 | 26 | >100 | >3.84 | – | 346.6 | 3.21 |
20 | CH3 | SO2CH3 | 19 | >100 | >5.26 | – | 337.6 | 3.82 |
21 | NH2 | SO2CH3 | 0.05 | >100 | >2,000 | 0.08 | 332.3 | 2.53 |
22 | CF3 | SO2CH3 | 0.22 | >100 | >454.5 | 0.15 | 352.3 | 4.26 |
23 | – | SO2CH3 | 6.2 | >100 | >16.1 | – | 332.6 | 3.18 |
24 | – | SO2CH3 | 0.82 | >100 | >121.9 | 0.7 | 344.6 | 1.20 |
25 | – | SO2CH3 | 5.2 | >100 | >19.2 | 11.0 | 352.4 | 2.34 |
28 | F | SO2CH3 | 0.14 | >100 | >714.2 | 0.2 | 380.8 | 4.89 |
29 | NH2 | SO2CH3 | 2.7 | >100 | >37.0 | 0.1 | 387.2 | 3.93 |
32 | F | H | 12.0 | 45.5 | 3.7 | 0.1 | 278.0 | 4.79 |
33 | NH2 | H | 8.6 | 57.9 | 6.73 | 0.1 | 284.3 | 3.83 |
5 | – | H | 18.1 | >100 | >5.5 | >1.0 | 232.9 | – |
14 | – | SO2CH3 | 4.4 | >100 | >22.7 | 10.0 | 226.1 | – |
1 | Celecoxib | 0.07 | >100 | >1428 | 0.09 | 298.6 | 4.34 | |
