Assessing the Bioisosterism of the Trifluoromethyl Group with a Protease Probe

Monika Jagodzinska, Florent Huguenot, Gabriele Candiani, Matteo Zanda

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)


The controversial bioisosterism of the trifluoromethyl group has been re-assessed by measuring the inhibitory potency of a set of barbiturates having CF3, CH3, CH3CH2, and (CH3)2CH groups as remote substituents occupying the bottom of the tight lipophilic tunnel-like S1' pocket of collagenase B as a steric probe. The results support the recent hypothesis that the CF3 group is, in terms of bioisosterism, “smaller” than the isopropyl, larger than the methyl, and rather similar to the ethyl group.

Original languageEnglish
Pages (from-to)49-51
Number of pages3
Issue number1
Early online date9 Dec 2008
Publication statusPublished - 12 Jan 2009


  • barbiturates
  • bioisosterism
  • isopropyl group
  • matrix metalloproteases
  • trifluoromethyl group
  • crystal-structure
  • inhibitors
  • fluorine
  • acid
  • derivatives
  • complex
  • design
  • chain


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