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- 01GMMX7NZ7BHYQK5VBSPMWSBHD classification A1.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD date "2018".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD language "eng".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD type journalArticle.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD subject "Chemistry".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD doi "10.1021/acs.jmedchem.8b01222".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD issn "0022-2623".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD issn "1520-4804".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD issue "23".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD volume "61".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD abstract "Fluorination is commonly employed to optimize bioactivity and pharmaco-kinetic properties of drug candidates. Aliphatic fluorination often reduces the lipophilicity (log P), but polyfluoroalkylation typically increases lipophilicity. Hence, identification of polyfluorinated motifs that nonetheless lead to similar or even reduced lipophilicities is of interest to expand the arsenal of medicinal chemistry tools in tackling properties such as compound metabolic stability or off-target selectivity. We show that changing a CF3-group of a perfluoroalkyl chain to a methyl group leads to a drastic reduction in lipophilicity. We also show that changing a C-F bond of a trifluoromethyl group, including when incorporated as part of a perfluoroalkyl group, to a C-Me group, leads to a reduction in log P, despite the resulting chain elongation. The observed lipophilicity trends were identified in fluorinated alkanol models and reproduced when incorporated in analogues of a drug candidate, and the metabolic stability of these motifs was demonstrated.".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author 1CD7F116-2AE5-11E3-A4E0-796A10BDE39D.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:00eab60e-3248-43ed-8c5b-ad242936ae91.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:047023b3-472f-4158-b99d-328242d8e5ff.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:776db025-256d-44b9-981d-4d3ede4bfc36.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:794e366c-8b50-463d-bc19-d4399a1b8e4d.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:7ede01be-bda8-44a5-9108-24352349b055.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:9e813a68-3293-4617-91d3-417910810068.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:d65d8c7c-48fa-40de-be28-425c9daa116b.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:e7a3a8df-4a5e-439e-84f6-409468480f3f.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD author urn:uuid:fc5a44c6-29ac-41d9-bb2d-abe4cdd043c6.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD dateCreated "2022-12-19T10:00:27Z".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD dateModified "2024-07-09T07:41:48Z".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD name "Reducing the lipophilicity of perfluoroalkyl groups by CF2-F/CF2-Me or CF3/CH3 exchange".
- 01GMMX7NZ7BHYQK5VBSPMWSBHD pagination urn:uuid:40ee54f9-e2bd-40fc-9dc8-aa0c89d6d623.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD sameAs LU-01GMMX7NZ7BHYQK5VBSPMWSBHD.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD sourceOrganization urn:uuid:08a72965-6c7e-45cf-b1f6-cbec9e36c8db.
- 01GMMX7NZ7BHYQK5VBSPMWSBHD type A1.