Novel aminopeptidase N (APN/CD13) inhibitors derived from chloramphenicol amine

Bioorg Med Chem. 2011 Sep 1;19(17):5190-8. doi: 10.1016/j.bmc.2011.07.008. Epub 2011 Jul 14.

Abstract

Aminopeptidase N (APN) is involved in different physiological and pathological processes of tumor cells, including proliferation, invasion, apoptosis and metastasis. Herein one series of compounds derived from commercially available (1S,2S)-2-amino-1-(4-nitrophenyl) propane-1,3-diol have been designed and synthesized. Furthermore, preliminary activity evaluation showed that some compounds elicited moderate inhibitory activity against APN with compounds 10e (IC(50)=6.1±0.5 μM) possessing the best efficacy, which could be used as the lead compound in the future for anticancer agents research.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry*
  • Amines / toxicity
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / toxicity
  • Binding Sites
  • CD13 Antigens / antagonists & inhibitors*
  • CD13 Antigens / metabolism
  • Chloramphenicol / chemistry*
  • Computer Simulation
  • Dipeptides / chemical synthesis
  • Dipeptides / chemistry*
  • Dipeptides / toxicity
  • Drug Screening Assays, Antitumor
  • Propanolamines / chemical synthesis
  • Propanolamines / chemistry*
  • Propanolamines / toxicity
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / chemistry*
  • Protease Inhibitors / toxicity
  • Structure-Activity Relationship

Substances

  • 2-amino-N-(1-(2-amino-3-(4-aminophenyl)-3-hydroxypropylamino)-1-oxo-3-phenylpropan-2-yl)-4-methylpentanamide
  • Amines
  • Antineoplastic Agents
  • Dipeptides
  • Propanolamines
  • Protease Inhibitors
  • Chloramphenicol
  • CD13 Antigens