Synthesis of omega-[18F]fluoroalkyl analogs of YM-09151-2 for the measurement of D2-dopamine receptors with PET

Int J Rad Appl Instrum A. 1990;41(6):551-5. doi: 10.1016/0883-2889(90)90038-i.

Abstract

Two [18F]fluoroalkyl analogs of a neuroleptic YM-09151-2 were synthesized via nucleophilic [18F]fluorination of methanesulfonyloxy- or p-toluenesulfonyloxyalkyl derivatives using no-carrier-added [18F]fluoride. Although 3-[18F]fluoropropylaminobenzamide was obtained in good yield, the yield of 2-[18F]fluoroethyl derivative was severalfold lower. The product, N-[(2RS,3RS)-1-benzyl-2-methylpyrrolidin-3-yl]-5- chloro-2-methoxy-4-(3-[18F]fluoropropyl)-aminobenzamide, was shown to have a striatum-to-cerebellum ratio comparable to that of 11C labeled YM-09151-2 and thus to be a good candidate for measuring D2-receptors in vivo.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzamides / chemical synthesis*
  • Benzamides / pharmacokinetics
  • Brain / diagnostic imaging*
  • Brain Chemistry
  • Fluorine Radioisotopes
  • Humans
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / pharmacokinetics
  • Male
  • Rats
  • Rats, Inbred Strains
  • Receptors, Dopamine / analysis*
  • Receptors, Dopamine D2
  • Tissue Distribution
  • Tomography, Emission-Computed*

Substances

  • Benzamides
  • Fluorine Radioisotopes
  • Hydrocarbons, Fluorinated
  • Receptors, Dopamine
  • Receptors, Dopamine D2
  • nemonapride