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• W3120559483 abstract "Given there is an optimal lipophilicity range for orally bioavailable drugs, structural modifications applied in the drug development process are not only focused on optimizing bioactivity but also on fine-tuning lipophilicity. Fluorine introduction can be used for both purposes. Insights into how fluorine introduction affects lipophilicity are thus of importance, and systematic series of fluorinated compounds with measured octanol–water partition coefficients are a powerful way to enhance our qualitative understanding in this regard and are essential as input for computational log P estimation programs. Here, we report a detailed comparison of all possible vicinal and skipped (1,3-substituted) fluorination motifs when embedded in structurally equivalent environments (X–CFnH2-n–CFmH2–m–X versus X–CFnH2–n–CH2–CFmH2–m–X, with n,m ≠ 0 and X = CH2OH) to compounds with isolated fluorination (n ≠ 0; m = 0, and including X–CH2–CFnH2–n–CH2–X, n = 0–2). It is shown that skipped fluorination is more powerful for log P reduction purposes compared to single or vicinal fluorination. Efficient stereoselective syntheses of the compounds with skipped fluorination motifs are reported, which where relevant can be made enantioselective using known chiral building blocks. These compounds, and some intermediates, will be of interest as advanced fluorinated building blocks." @default.
• W3120559483 created "2021-01-18" @default.
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• W3120559483 date "2021-01-05" @default.
• W3120559483 modified "2023-10-15" @default.
• W3120559483 title "Skipped Fluorination Motifs: Synthesis of Building Blocks and Comparison of Lipophilicity Trends with Vicinal and Isolated Fluorination Motifs" @default.
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• W3120559483 doi "https://doi.org/10.1021/acs.joc.0c02810" @default.
• W3120559483 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33400526" @default.
• W3120559483 hasPublicationYear "2021" @default.
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