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• W2317145906 abstract "The improved chiral synthesis of the selective dopamine D3 receptor (D3R) antagonist (R)-N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)-3-hydroxybutyl)1H-indole-2-carboxamide (( R )-PG648) is described. The same chiral secondary alcohol intermediate was used to prepare the enantiomers of a 3-F-benzofuranyl analogue, BAK 2-66. The absolute configurations of the 3-F enantiomers were assigned from their X-ray crystal structures that confirmed retention of configuration during fluorination with N,N-diethylaminosulfur trifluoride (DAST). ( R )-BAK2-66 showed higher D3R affinity and selectivity than its (S)-enantiomer; however, it had lower D3R affinity and enantioselectivity than ( R )-PG648. Further, importance of the 4-atom linker length between the aryl amide and 4-phenylpiperazine was demonstrated with the 4-fluorobutyl-product (8)." @default.
• W2317145906 created "2016-06-24" @default.
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• W2317145906 date "2014-03-27" @default.
• W2317145906 modified "2023-10-10" @default.
• W2317145906 title "Chiral Resolution and Serendipitous Fluorination Reaction for the Selective Dopamine D3 Receptor Antagonist BAK2-66" @default.
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• W2317145906 doi "https://doi.org/10.1021/ml500006v" @default.
• W2317145906 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4060923" @default.
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