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. Author manuscript; available in PMC: 2023 Oct 27.
Published in final edited form as: J Med Chem. 2022 Oct 11;65(20):13910–13934. doi: 10.1021/acs.jmedchem.2c01151

Table 5.

Fluorine Substitutionsa

graphic file with name nihms-1861478-t0006.jpg
compound C-5 C-6 C-7 C-8 C-2 R MIC (μg/mL) clog P
68 H H CF3 H CHF2 3,4-dichlorophenyl 1 6.3
69 H H CF3 H CHF2 3-(trifluoromethoxy)phenyl 0.5 6.6
74 H H F H CF3 3,4-dichlorophenyl 0.5 7.0
75 H H F H CF3 3-(trifluoromethoxy)phenyl 2 6.7
76 H H F H CF3 5-(trifluoromethyl)pyridin-2-yl 1 5.3
77 F F H H CF3 5-(trifluoromethyl)pyridin-2-yl 16–32 5.3
78 H F F H CF3 5-(trifluoromethyl)pyridin-2-yl 0.25 5.3
79 F F H F CF3 5-(trifluoromethyl)pyridin-2-yl >32 5.5
a

C-2 refers to the position of the quinoline scaffold. Similarly, C-5, C-6, C-7, and C-8 refer to the respective positions on the quinoline nucleus.