New fluorinated dopamine D2 ligands with benzofuran skeleton. The synthesis and in vitro evaluation

DOI: 10.1248/cpb.41.296

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 296 - 300 (1993)

Update date:2022-09-26

Topics: Fluorination Structure-Activity Relationship (SAR) Analysis Purification and characterization Chemical Synthesis In Vitro Evaluation Publication and Reporting Pharmacological Testing

Authors:

Sasaki Sasaki

Takao Takao

Watanabe

Obana Obana

Maeda Maeda

Fukumura

Takehara

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Article abstract of DOI:10.1248/cpb.41.296

New fluorinated ligands with N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydrobenzofuran-7-carboxamide skeleton, which are useful as a prototype to develop ¹⁸F labelled in vivo radiotracer for positron emission tomography (PET), were synthesized, and their binding affinities for the dopamine D2 receptors were investigated. Fluorine atom was introduced at C-4 of the pyrrolidine ring (10) or at ethyl substituent at C-5 of the dihydrobenzofuran moiety (20). The in vitro IC₅₀ values of these ligands for the dopamine D2 receptors which were determined by their ability to inhibit the binding of [³H]spiperone binding in rat striatal membrane were 17 and 36 nM, respectively. Thus, the fluorinated compounds 10 and 20 may be possible candidates for further in vivo investigation.