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Table 2 MMP inhibition potencies and clogD (logD) values of lead structures and target novel hydroxamic acids

From: Synthesis, radiosynthesis, in vitro and first in vivo evaluation of a new matrix metalloproteinase inhibitor based on γ-fluorinated α-sulfonylaminohydroxamic acid

  IC50 [nM]a log D values
Compound R X MMP-2 MMP-9 clogDb logD (exp.) Ref.
(R)-CGS 27023A CH3 N 20c 8c 1.49   (Mac Pherson et al., 1997)
(R)-CGS 25966 CH3 CH 11c 27c 2.72   (Scozzafava and Supuran, 2000)
(R)-FEtO- CGS 25966 CH2CH2F CH 4 ± 3 50 ± 27 2.92 2.02 ± 0.03 (Wagner et al., 2011)
(R)-2 CH3 N 9.3 ± 2.0 8.3 ± 0.1 0.81   (Behrends et al., 2015)
(S)-2 CH3 N 7.2 ± 0.1 4.9 ± 0.4 0.81   (Behrends et al., 2015)
(R)-9a CH2CH2F CH 10.4 ± 5.9 0.5 ± 0.3 2.23   
(S)-9a CH2CH2F CH 0.3 ± 0.03 0.1 ± 0.01 2.23 1.16 ± 0.2d  
  1. aStandard deviations based on three independent experiments are given for IC50 values in nM range
  2. bclogD values were calculated by ChemAxon LogD predictor, (logD = logP at physiological pH 7.4)
  3. cKi values, where SDs are not denoted
  4. dlogD value was determined for compound (S)-[18F]9a