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. 2015 Jul 17;6(8):861–865. doi: 10.1021/acsmedchemlett.5b00048

Table 4. Effects of Trifluoromethylation at R1, R2, and R3.

graphic file with name ml-2015-00048j_0005.jpg

Cpd * R1 R2 R3 hCYP11B2a (IC50, nM) hCYP11B1a (IC50, nM) B1/B2b LLEc logDd
14   CH3 CH3 CH3 283 >8333 29 4.38 0.6
18   CF3 CH3 CH3 526 1473 3 3.02 1.5
19 (S) CH3 CH3 CF3 64 4402 69 4.36 1.2
20 (R) CH3 CF3 CH3 109 >8333 76 4.13 1.2
21 (S) CF3 CH3 CF3 461 887 2 2.42 2.2
22 (R) CF3 CF3 CH3 476 >8333 >18 2.41 2.2
a

IC50s calculated from n ≥ 2, see Supporting Information for details.

b

Ratio of hCYP11B1 IC50/hCYP11B2 IC50.

c

Ligand lipophilic efficiency; LLE = pIC50 – aLogP98.

d

Determined experimentally by HPLC.