An improved design of fluorophilic molecules: prediction of the ln P fluorous partition coefficient, fluorophilicity, using 3D QSAR descriptors and neural networks

Synthesis, physicochemical properties and in vitro cytotoxicity of nicotinic acid ester prodrugs intended for pulmonary delivery using perfluorooctyl bromide as vehicle

“…This partition coefficient has the advantage that it can be easily determined experimentally or estimated using a variety of theoretical approaches (Daniels et al, 2004;Duchowicz et al, 2004;Kiss et al, 2001). The PFMC-toluene partition coefficients of all nicotinates fall into a relatively narrow range from log K p (PFMC/toluene) = −2.62 to −0.70 (Table 1).…”

“…Typical fluorophilic molecules have a fluorine content > 60 wt. %, at least one long fluorous tail, and contain no or few functional groups allowing attractive intermolecular interactions (Kiss et al, 2001). All nicotinates, including C8F15, have a fluorine content below 60 wt.% and, with exception of C8F13 and C8F15, the fluorous tail is very short and are therefore expected not to be fluorophilic.…”

Partition Coefficients Involving Fluorous Solvents

“…One approach makes use of 3D QSAR descriptors and neural networks [4]. A host of parameters was considered: percent fluorine, molecular volume, molecular surface, globularity, solvent accessible surface, solvent extended surface, solvent extended volume, calculated polarizability, calculated dipole moment, calculated Hildebrand parameter, degree of chemical bond rotational freedom, and others.…”

Convenient Syntheses of Fluorous Aryl Iodides and Hypervalent Iodine Compounds: ArI(L)n Reagents That Are Recoverable by Simple Liquid/Liquid Biphase Workups, and Applications in Oxidations of Hydroquinones

“…We [17] and several other groups [18] have described simple fluorous aryl bromides such as p-BrC 6 H 4 (CH 2 ) m R fn (m/n 2/6, 2/8, 3/8), and used these as precursors to a variety of other fluorous molecules. However, compounds that contain only one pony tail per aromatic [4,18,20] or heteroaromatic [20,21] ring exhibit low fluorous phase affinities.…”