Table 4.
Antibacterial activity of 3-phenylaminopyridinium Analogs, 12a-s
 |
|||||
|---|---|---|---|---|---|
| Compound | IC50 /MIC/MBC (μg/mL) | ||||
| Entry | R | Sa | MRSA | E. Coli | M. int. |
| 12a | H | 0.7/1.3/10 | 3.4/10/20 | 7.6>20/>20 | 2.1/25/2.5 |
| 12b | o-Cl | 0.3/0.6/10 | 1.1/2.5/10 | 7.6/>20/>20 | 2.1/2.5/5.0 |
| 12c | m-Cl | 0.34/0.63/5.0 | 1.3/2.5/5.0 | 6.5/>20/>20 | 2.1/2.5/5.0 |
| 12d | p-Cl | 1.5/3.1/NT | NT | NT | 1.0/1.6/NT |
| 12e | o-CF3 | 0.3/0.3/10 | 0.6/1.3/5.0 | 9.1/>20/>20 | 1.2/3.5/2.5 |
| 12f | m-CF3 | NT | 1.5/2.5/5.0 | 4.5/>20/>20 | 2.0/2.5/2.5 |
| 12g | p-CF3 | NT | 0.9/2.5/2.5 | 3.5/20/20 | 1.0/1.3/1.3 |
| 12h | p-F | 0.7/1.3/10 | 3.0/5.0/20 | 18/>20/>20 | 3.2/5.0/10.0 |
| 12i | o-CH3 | 0.3/0.6/10 | 1.0/2.5/10 | 9.4/>20/>20 | 1.6/2.5/2.5 |
| 12j | m-CH3 | 0.7/1.3/5.0 | 1.2/2.5/5.0 | 7.7/>20/>20 | 1.1/1.3/5.0 |
| 12k | p-CH3 | NT | 1.0/2.5/2.5 | 4.5/20/>20 | 1.5/2.5/2.5 |
| 12l | p-C2H5 | 0.2/3.0/5.0 | 0.7/1.3/2.5 | 4.0/20/20 | 0.6/1.3/5.0 |
| 12m | p-SCH3 | 0.3/0.6/5.0 | 1.0/2.5/2.5 | 5.2/20/20 | 1.0/1.3/5.0 |
| 12n | o-OCH3 | 0.4/0.6/20 | 1.2/5.0/20 | 14/>20/>20 | 1.9/2.5/2.5 |
| 12o | m-OCH3 | 0.8/1.3/20.0 | 4.8/10/20 | NA | 3.3/5.0/10 |
| 12p | p-OCH3 | 0.3/0.6/10.0 | 1.9/5.0/10 | 5.4/>20/>20 | 1.0/1.3/5.0 |
| 12q | o-CN | 1.3/2.5/10.0 | 6.4/20/20 | NA | 3.5/5.0/20 |
| 12r | m-CN | 0.8/1.3/20 | 3.9/10/10 | NA | 2.0/2.5/10 |
| 12s | p-CN | 2.5/5.0/20 | 6.2/10/20 | NA | 2.8/5.0/5.0 |
| Cryptolepine a | 10 ( IC50) | 20 ( IC50) | NT | 15 ( IC50) | |
| Ciprofloxacin | 0.07/0.3/0.5 | 0.07/0.3/0.5 | 0.005/0.3/0.6 | 0.3/0.5/>20 | |
Abbreviations: Sa = Staphylococcus aureus, MRSA = Methicillin-resistant Staphylococcus aureus, M. Int. = Mycobacterium intracellulare. NT = Not tested. NA = not active at 20 μg/mL· IC50 = The concentration that affords 50% inhibition of growth, MIC = Minimum inhibitory concentration and is the lowest test concentration that allows no detectable growth; MFC = Minimum bactericidal concentration and is the lowest test concentration that kills the microorganism; TC50 = The concentration that is toxic to 50% of cells. The syntheses and characterization of all compounds in this Table were previously reported [3].
a
Data previously reported [10].