Medicinal Applications of Perfluoroalkylated Chain-Containing Compounds

Abstract

Compounds with polyfluorinated molecular fragments possess unique properties associated with the presence of a large number of fluorine atoms that affect lipophilicity and conformational rigidity of the parent molecule along with other effects. The aim of this review is to provide an overview of synthesized compounds possessing perfluoroalkylated or polyfluorinated chains that have been tested for bioactivity or as potential drug candidates for the treatment of various diseases. As far as the length of the perfluoroalkylated chain is concerned the focus is centered on the compound bearing perfluoroethyl or tetrafluoroethyl as well as longer chains. The perfluoroalkylated compounds discussed are classified according to their biological activity.

Conformational Plasticity in Glycomimetics: Fluorocarbamethyl‐L‐idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings

“…It could inducei ncrease of lipophilicity,d ecreasei np K a values of certain groups by OH-F electrostatic interaction, modulate the hydrogen-bond acceptor/donator ability or foster the presence of ap articular ring conformation. [17] In this context, difluorinated carbasugars have been recently synthesized. [18][19][20] Their suitability to act as improved sugar analogues has been studied.I ndeed, the presence of fluorine atoms emulates, toac ertain degree, the properties of the endocyclic oxygen [20] and, consequently,t hey are betterc andidates to mimic naturalg lycans than their non-fluorinated analogues.…”

Design and synthesis of glycomimetics: Recent advances

“…Depending on the substituted position, fluorine substituents can have remarkable effects upon the physical and chemical properties of the molecule. A fluorine atom can induce increase of lipophilicity, decrease in pKa values of certain groups by OH–F electrostatic interaction, can modulate the hydrogen‐bond acceptor/donor ability or foster the presence of a particular ring conformation . This feature has been exploited in many ways for the development of enzyme inhibitors, as seen before in section 2.1, or to make the molecule resistant to chemical degradation.…”

Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (RF) Groups: Electron Affinities of PAH(RF)n Increase Significantly with Increasing RF Chain Length

“…We show that changing the R F groupsf rom CF 3 to n-C 4 F 9 can increase the EA by up to four times the increasep reviously observed fort he C 60 (R F ) 2 compounds. For as eries of NAPH(R F ) 4 compounds, the increasei nE Af rom CF 3 to n-C 4 F 9 is nearly one-third of an electron volt. As far as we know,t his is the first systematic study of the effect on EA of lengthening the chain of n-R F groupsa ttached to the C(sp 2 )a toms of substrates with extended p-systems.…”

“…n-Perfluoroalkyl groups are an importants eries of homologous substituents for both organic [1][2][3][4][5][6] and inorganic compounds. [7][8][9][10][11] The number of carbon atoms in these straight-chain substituents commonly varies from 1t o8by single integers.…”