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. Author manuscript; available in PMC: 2022 Feb 21.
Published in final edited form as: J Med Chem. 2018 May 14;61(12):5162–5186. doi: 10.1021/acs.jmedchem.7b01862

Table 2.

Biological Activity of Quinolone R2 Carboxylic Acids and Methyl Esters with R1 Pyridine and Pyrimidine Moietiesa

graphic file with name nihms-1775450-t0022.jpg
DHODH Assay MTT Assay
# R1 R2 IC50 (μM) cLogP LipE HCT-116 IC50 (μM) MIA PaCa-2 IC50 (μM)
13 graphic file with name nihms-1775450-t0023.jpg CO2H 10.1 ± 2.4 4.47 0.53 39.6 ± 14 49.3 ± 36
14 graphic file with name nihms-1775450-t0024.jpg CO2H 0.391 ± 0.090 4.26 2.15 20.9 ± 6.4 32.8 ± 7.0
15 graphic file with name nihms-1775450-t0025.jpg CO2Me >200 4.49 NA 6.15 ± 2.9 6.43 ± 3.0
16 graphic file with name nihms-1775450-t0026.jpg CO2H 7.55 ± 1.3 4.26 0.86 33.6 ± 2.6 68.1 ± 27
17 graphic file with name nihms-1775450-t0027.jpg CO2H 0.165 ± 0.086 4.02 2.76 5.60 ± 0.88 13.6 ± 2.7
18 graphic file with name nihms-1775450-t0028.jpg CO2H 0.127 ± 0.022 5.12 1.78 2.85 ± 1.1 7.45 ± 2.8
19 graphic file with name nihms-1775450-t0029.jpg CO2H >200 2.76 NA >50 >50
20 graphic file with name nihms-1775450-t0030.jpg CO2H 8.21 ± 2.8 3.24 1.85 > 50 >50
21 graphic file with name nihms-1775450-t0031.jpg CO2H >200 2.97 NA >50 >50
a

Data for cLogP values was predicted using ChemBioDraw Professional 16. Lipophilic ligand efficiency (LipE) calculated LipE = −pIC50 (M) – cLogP.33