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. 2017 Dec 15;9(1):51–55. doi: 10.1021/acsmedchemlett.7b00431

Table 1. Results from Paraben Derivative Synthesis and Antimicrobial Screening against S. aureus.

graphic file with name ml-2017-004315_0003.jpg

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)
a

Not soluble at the higher 512 μg/mL concentration and therefore was not tested.

b

Equivalent to butyl ester (2) with X, Y, Z = H, H, H.