Table 1. Results from Paraben Derivative Synthesis and Antimicrobial Screening against S. aureus.
X, Y, Z | ROH | compd | rxn time (h) | rxn yield (%) | S. aureus MIC μg/mL (μM) |
---|---|---|---|---|---|
F, F, F | BuOH | 2a | 18 | 35 | 128 (483) |
Cl, Cl, H | BuOH | 2b | 18 | 65 | 64 (245) |
Br, Br, H | BuOH | 2c | 18 | 53 | 32 (91) |
Br, H, H | BuOH | 2d | 18 | 66 | 64 (236) |
I, I, H | BuOH | 2e | 1 | 75 | 16 (36) |
I, H, H | BuOH | 2f | 18 | 42 | 64 (199) |
CH3, CH3, H | BuOH | 2g | 18 | 70 | >256a (>1045) |
tBu, tBu, H | BuOH | 2h | 18 | 67 | >256a (834) |
OH, OH, H | BuOH | 2i | 18 | 50 | 512 (2055) |
OMe, OMe, H | BuOH | 2j | 18 | 88 | >256a (924) |
NO2, NO2, H | BuOH | 2k | 3 | 56 | 512 (1809) |
I, I, H | OctOH | 3e | 1 | 59 | 16 (31.8) |
CH3, CH3, H | OctOH | 3g | 18 | 71 | 64 (213) |
OH, OH, H | OctOH | 3i | 18 | 40 | 64 (210) |
NO2, NO2, H | OctOH | 3k | 18 | 82 | 16 (47) |
butyl parabenb | 256 (1320) | ||||
penicillin G | 0.25 (0.749) |
Not soluble at the higher 512 μg/mL concentration and therefore was not tested.
Equivalent to butyl ester (2) with X, Y, Z = H, H, H.