Table 2 Molecular parameters of 7-chloro-4-aminoquinoline based semicarbazones and thiosemicarbazones (6a-i), (7a-i), (8a-i), and (9a-i)
Compounds | TPSA | n-rotb | nON | nOHNH | miLogp | MW |
|---|---|---|---|---|---|---|
Rule of 5 | – | – | ≤ 10 | ≤ 5 | ≤ 5 | ≤ 500 |
6a | 75.33 | 7 | 5 | 4 | 7.101 | 472 |
6b | 84.567 | 8 | 6 | 4 | 6.71 | 488 |
6c | 93.801 | 9 | 7 | 4 | 6.299 | 518 |
6d | 103.035 | 10 | 8 | 4 | 6.284 | 548 |
6e | 75.333 | 7 | 5 | 4 | 7.331 | 492 |
6f | 75.333 | 7 | 5 | 4 | 6.817 | 475 |
6 g | 75.333 | 7 | 5 | 4 | 7.462 | 536 |
6 h | 121.157 | 8 | 8 | 4 | 6.612 | 502 |
6i | 95.561 | 7 | 6 | 5 | 6.174 | 473 |
7a | 92.404 | 6 | 6 | 4 | 6.561 | 455 |
7b | 101.638 | 7 | 7 | 4 | 6.169 | 471 |
7c | 110.872 | 8 | 8 | 4 | 5.759 | 501 |
7d | 120.106 | 9 | 9 | 4 | 5.743 | 532 |
7e | 92.404 | 6 | 6 | 4 | 6.79 | 476 |
7f | 92.404 | 6 | 6 | 4 | 6.276 | 459 |
7 g | 92.404 | 6 | 6 | 4 | 6.921 | 520 |
7 h | 138.228 | 7 | 9 | 4 | 6.071 | 486 |
7i | 112.632 | 6 | 7 | 5 | 5.633 | 457 |
8a | 75.333 | 7 | 5 | 4 | 7.077 | 472 |
8b | 84.567 | 8 | 6 | 4 | 6.686 | 488 |
8c | 93.801 | 9 | 7 | 4 | 6.275 | 518 |
8d | 103.035 | 10 | 8 | 4 | 6.26 | 548 |
8e | 75.333 | 7 | 5 | 4 | 7.307 | 492 |
8f | 75.333 | 7 | 5 | 4 | 6.793 | 475 |
8 g | 75.333 | 7 | 5 | 4 | 7.438 | 536 |
8 h | 121.157 | 8 | 8 | 4 | 6.588 | 502 |
8i | 95.561 | 7 | 6 | 5 | 6.15 | 473 |
9a | 92.404 | 6 | 6 | 4 | 6.537 | 455 |
9b | 101.638 | 7 | 7 | 4 | 6.145 | 471 |
9c | 110.872 | 8 | 8 | 4 | 5.735 | 501 |
9d | 120.106 | 9 | 9 | 4 | 5.719 | 532 |
9e | 92.404 | 6 | 6 | 4 | 6.766 | 476 |
9f | 92.404 | 6 | 6 | 4 | 6.252 | 459 |
9 g | 92.404 | 6 | 6 | 4 | 6.897 | 520 |
9 h | 138.228 | 7 | 9 | 4 | 6.047 | 486 |
9i | 112.632 | 6 | 7 | 5 | 5.609 | 457 |
INH | 68.013 | 1 | 4 | 3 | − 0.969 | 137 |
Pyra | 68.878 | 1 | 4 | 2 | − 0.711 | 123 |
Cipro | 74.569 | 3 | 6 | 2 | − 0.701 | 331 |