4-Trifluoromethoxy proline: synthesis of stereoisomers and lipophilicity study.

Logvinenko, Ivan G; Sadkova, Iryna V; Tolmachova, Nataliya A; Shishkina, Svitlana V; Daniliuc, Constantin G; Haufe, Günter; Kondratov, Ivan S

Logvinenko, Ivan G; Sadkova, Iryna V; Tolmachova, Nataliya A; Shishkina, Svitlana V; Daniliuc, Constantin G; Haufe, Günter; Kondratov, Ivan S.

Affiliation

Logvinenko IG; Enamine Ltd, Winston Churchill Str. 78, Kyiv 02094, Ukraine.
Sadkova IV; Address V.P. Kukhar Institute of Bioorganic Chemistry & Petrochemistry, National Academy of Sciences of Ukraine, Academician Kukhar Str. 1, Kyiv 02094, Ukraine.
Tolmachova NA; Enamine Ltd, Winston Churchill Str. 78, Kyiv 02094, Ukraine.
Shishkina SV; Enamine Ltd, Winston Churchill Str. 78, Kyiv 02094, Ukraine.
Daniliuc CG; SSI "Institute for Single Crystals" of the National Academy of Sciences of Ukraine, Nauky Ave. 60, Kharkiv 61072, Ukraine.
Haufe G; Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Academician Kukhar Str. Str. 5, Kyiv 02660, Ukraine.
Kondratov IS; Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, Münster 48149, Germany.

Org Biomol Chem ; 22(39): 7982-7988, 2024 Oct 09.

Article in En | MEDLINE | ID: mdl-38973538

ABSTRACT

ABSTRACT

All four stereoisomers of 4-CF3O-proline have been synthesized through a fluorodesulfurization approach using the corresponding 4-hydroxyprolines as starting materials. The investigation of their lipophilicity characteristics and comparison with those of other 4-substituted proline analogs demonstrated a similar impact of CF3 and CF3O groups on log D.

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Full text: 1 Database: MEDLINE Language: En Journal: Org Biomol Chem / Org. biomol. chem / Organic & biomolecular chemistry Journal subject: BIOQUIMICA / QUIMICA Year: 2024 Type: Article Affiliation country: Ukraine

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