Amino substituted analogs of 1-phenyl-3-phenylimino-2-indolones with potent galanin Gal3 receptor binding affinity and improved solubility

Bioorg Med Chem Lett. 2006 Aug 1;16(15):3950-4. doi: 10.1016/j.bmcl.2006.05.025. Epub 2006 May 30.

Abstract

A series of amino analogs of 1,3-dihydro-1-phenyl-3-[[3-(trifluoromethyl)phenyl]imino]-2H-indol-2-one (1) were synthesized to improve aqueous solubility, while retaining high affinity for the human galanin Gal3 receptor. A very potent analog (9e, 1,3-dihydro-1-[3-(2-pyrrolidinylethoxy)phenyl]-3-[[3-(trifluoromethyl)phenyl]imino]-2H-indol-2-one, Ki=5 nM) shows good selectivity and solubility of 48 microg/mL at pH 7.4.

MeSH terms

  • Amines / chemistry*
  • Indoles / chemistry*
  • Indoles / metabolism
  • Indoles / pharmacology*
  • Receptor, Galanin, Type 3 / drug effects*
  • Receptor, Galanin, Type 3 / metabolism
  • Solubility

Substances

  • Amines
  • Indoles
  • Receptor, Galanin, Type 3