The discovery of non-benzimidazole and brain-penetrant prolylcarboxypeptidase inhibitors

Bioorg Med Chem Lett. 2012 Jan 1;22(1):658-65. doi: 10.1016/j.bmcl.2011.10.060. Epub 2011 Oct 24.

Abstract

Novel prolylcarboxypeptidase (PrCP) inhibitors with nanomolar IC(50) values were prepared by replacing the previously described dichlorobenzimidazole-substituted pyrrolidine amides with a variety of substituted benzylamine amides. In contrast to prior series, the compounds demonstrated minimal inhibition shift in whole serum and minimal recognition by P-glycoprotein (P-gp) efflux transporters. The compounds were also cell permeable and demonstrated in vivo brain exposure. The in vivo effect of compound (S)-6e on weight loss in an established diet-induced obesity (eDIO) mouse model was studied.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B / genetics
  • ATP Binding Cassette Transporter, Subfamily B / metabolism
  • Amides / chemistry
  • Animals
  • Benzimidazoles / pharmacology*
  • Biological Transport
  • Body Weight
  • Brain / drug effects
  • Brain / metabolism*
  • Carboxypeptidases / antagonists & inhibitors*
  • Disease Models, Animal
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Models, Chemical
  • Obesity / drug therapy
  • Pyrrolidines / chemistry
  • Time Factors

Substances

  • ATP Binding Cassette Transporter, Subfamily B
  • Amides
  • Benzimidazoles
  • Pyrrolidines
  • multidrug resistance protein 3
  • Carboxypeptidases
  • lysosomal Pro-X carboxypeptidase
  • pyrrolidine