Synthesis and biological evaluation of halogenated naphthyridone carboxamides as potential ligands for in vivo imaging studies of substance P receptors

Bioconjug Chem. 2003 May-Jun;14(3):629-41. doi: 10.1021/bc025656r.

Abstract

With the aim of developing new radioligands for in vivo studies of substance P receptors using positron emission tomography or single photon emission computed tomography, 2- and 3-halo naphthyridone-6-carboxamide derivatives were synthesized. Their affinities toward the target receptors were evaluated on CHO cells and compared to the unsubstituted analogue EP 00652218 (IC(50) = 100 nM +/- 20). The IC(50) value was not altered in the case of 2-chloro compound 1 (IC(50) = 100 nM +/- 15) and only slightly reduced for the 2-fluoro and -iodo analogues 6 and 8 (IC(50) = 500 nM +/- 80). A drastic reduction in binding (IC(50) > 1000 nM) was observed for the halogenated compounds 2-5, 7, and 9.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biotransformation
  • CHO Cells
  • Cricetinae
  • Drug Evaluation, Preclinical / methods
  • Halogens / chemical synthesis
  • Halogens / metabolism*
  • Hydrolysis
  • Ligands
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / metabolism*
  • Radioligand Assay / methods
  • Receptors, Neurokinin-1 / metabolism*
  • Tomography, Emission-Computed / methods*
  • Tomography, Emission-Computed, Single-Photon / methods

Substances

  • Halogens
  • Ligands
  • Naphthyridines
  • Receptors, Neurokinin-1