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Synthesis, physico-chemical properties and microsomal stability of compounds bearing aliphatic trifluoromethoxy group

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Markushyna,  Yevheniia
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Logvinenko, I. G., Markushyna, Y., Kondratov, I. S., Vashchenko, B. V., Kliachyna, M., Tokaryeva, Y., et al. (2020). Synthesis, physico-chemical properties and microsomal stability of compounds bearing aliphatic trifluoromethoxy group. Journal of Fluorine Chemistry, 231: 109461. doi:10.1016/j.jfluchem.2020.109461.


Cite as: http://hdl.handle.net/21.11116/0000-0005-9BF3-A
Abstract
Effects of the trifluoromethoxy substituent on physico-chemical properties of compounds, such as kinetic solubility, lipophilicity and microsomal clearance, was studied in a series of aliphatic derivatives. It was found that kinetic solubility of the CF3O-containing compounds was comparable to that of analogs, i.e. compounds bearing CH3O and CF3 moieties. The CF3O-substituted compounds had higher lipophilicity as compared to methoxy analogues, and nearly the same like CF3-bearing compounds. Microsomal stability studies indicated that the trifluoromethoxy group typically decreased metabolic stability of the corresponding derivatives as compared to either CH3O- or CF3-substituted counterparts, except for N-alkoxy(sulfon)amide series.