Fluorine in Pharmaceuticals: Looking Beyond Intuition Export

@article{citeulike:1723757, abstract = {Fluorine substituents have become a widespread and important drug component, their introduction facilitated by the development of safe and selective fluorinating agents. Organofluorine affects nearly all physical and adsorption, distribution, metabolism, and excretion properties of a lead compound. Its inductive effects are relatively well understood, enhancing bioavailability, for example, by reducing the basicity of neighboring amines. In contrast, exploration of the specific influence of carbon-fluorine single bonds on docking interactions, whether through direct contact with the protein or through stereoelectronic effects on molecular conformation of the drug, has only recently begun. Here, we review experimental progress in this vein and add complementary analysis based on comprehensive searches in the Cambridge Structural Database and the Protein Data Bank. 10.1126/science.1131943}, author = {Muller, Klaus and Faeh, Christoph and Diederich, Francois}, citeulike-article-id = {1723757}, citeulike-linkout-0 = {http://dx.doi.org/10.1126/science.1131943}, citeulike-linkout-1 = {http://www.sciencemag.org/cgi/content/abstract/317/5846/1881}, citeulike-linkout-2 = {http://view.ncbi.nlm.nih.gov/pubmed/17901324}, citeulike-linkout-3 = {http://www.hubmed.org/display.cgi?uids=17901324}, day = {28}, doi = {10.1126/science.1131943}, journal = {Science}, keywords = {flurorine, geometry, modeling, protein\_ligand\_interaction, roche}, month = {September}, number = {5846}, pages = {1881--1886}, posted-at = {2009-03-13 12:48:42}, priority = {2}, title = {Fluorine in Pharmaceuticals: Looking Beyond Intuition}, url = {http://dx.doi.org/10.1126/science.1131943}, volume = {317}, year = {2007} }

TY - JOUR ID - citeulike:1723757 L3 - citeulike-article-id:1723757 N2 - Fluorine substituents have become a widespread and important drug component, their introduction facilitated by the development of safe and selective fluorinating agents. Organofluorine affects nearly all physical and adsorption, distribution, metabolism, and excretion properties of a lead compound. Its inductive effects are relatively well understood, enhancing bioavailability, for example, by reducing the basicity of neighboring amines. In contrast, exploration of the specific influence of carbon-fluorine single bonds on docking interactions, whether through direct contact with the protein or through stereoelectronic effects on molecular conformation of the drug, has only recently begun. Here, we review experimental progress in this vein and add complementary analysis based on comprehensive searches in the Cambridge Structural Database and the Protein Data Bank. 10.1126/science.1131943 IS - 5846 JF - Science EP - 1886 TI - Fluorine in Pharmaceuticals: Looking Beyond Intuition VL - 317 SP - 1881 KW - flurorine KW - geometry KW - modeling KW - protein_ligand_interaction KW - roche AU - Muller, Klaus AU - Faeh, Christoph AU - Diederich, Francois PY - 2007/09/28/ UR - http://dx.doi.org/10.1126/science.1131943 ER -