Stereopure β-Hydroxy Cycloalkane Carboxylic Acids and Their Fluorinated Derivatives as Promising Chemotypes for Drug Discovery: Multigram Synthesis, Physicochemical and Biological Evaluation
Тип публікації :
Препринт
Дата випуску :
4 червня 2026 р.
Автор(и) :
Тatiana Borisova
eKNUTSHIR URL :
Журнал :
ChemRxiv
Цитування :
[APA 7] Тatiana, B. (2026). Stereopure β-Hydroxy Cycloalkane Carboxylic Acids and Their Fluorinated Derivatives as Promising Chemotypes for Drug Discovery: Multigram Synthesis, Physicochemical and Biological Evaluation. ChemRxiv,. https://doi.org/10.26434/chemrxiv.15004297/v1
[ДСТУ] Тatiana B. Stereopure β-Hydroxy Cycloalkane Carboxylic Acids and Their Fluorinated Derivatives as Promising Chemotypes for Drug Discovery: Multigram Synthesis, Physicochemical and Biological Evaluation. ChemRxiv. 2026. DOI: 10.26434/chemrxiv.15004297/v1 (дата звернення: 11.09.2026).
An efficient synthetic approach to all stereoisomers of enantiopure β-hydroxycycloalkane carboxylic acids based on enzymatic resolution of appropriate synthetic equivalents was developed. The developed methodology was used for the preparation of other building blocks relevant to medicinal chemistry, including β-methoxy- and β-fluoro-substituted cycloalkane carboxylic acids. In addition to that, diastereopure gem-difluorinated β-hydroxycycloalkane carboxylic acids were also synthesized. The obtained series of building blocks was subjected to physicochemical characterization, including p K a and Log P measurements. Furthermore, they were used to synthesize serotonin receptor modulators that were evaluated in an animal study using isolated rat cortex nerve terminals and measuring the mitochondrial membrane potential and ROS generation with fluorimetry along with serotonin.
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