Fluorine in Pharmaceuticals: Looking Beyond Intuition
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[1] F. Leroux. Atropisomerism, Biphenyls, and Fluorine: A Comparison of Rotational Barriers and Twist Angles , 2004, Chembiochem : a European journal of chemical biology.
[2] J. Hernández‐Trujillo,et al. Molecular Quadrupole Moments for the Series of Fluoro- and Chlorobenzenes , 1996 .
[3] M. Wilson,et al. Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus. , 1990, Journal of medicinal chemistry.
[4] Justin C. Biffinger,et al. The Polar Hydrophobicity of Fluorinated Compounds , 2004, Chembiochem : a European journal of chemical biology.
[5] T. Maren,et al. A new class of carbonic anhydrase inhibitor. , 1993, The Journal of biological chemistry.
[6] Martin Stahl,et al. Fluorine in Medicinal Chemistry , 2004, Chembiochem : a European journal of chemical biology.
[7] M. Schlosser. CF(3)-bearing aromatic and heterocyclic building blocks. , 2006, Angewandte Chemie.
[8] J. Matsumoto,et al. 1,4-Dihydro-4-oxopyridinecarboxylic acids as antibacterial agents. 2. Synthesis and structure-activity relationships of 1,6,7-trisubstituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids, including enoxacin, a new antibacterial agent , 1984 .
[9] Alex Avdeef,et al. Physicochemical Profiling (Solubility, Permeability and Charge State) , 2001 .
[10] Manfred Kansy,et al. Fluorine Interactions at the Thrombin Active Site: Protein Backbone Fragments HCαCO Comprise a Favorable CF Environment and Interactions of CF with Electrophiles , 2004, Chembiochem : a European journal of chemical biology.
[11] E. LaVoie,et al. Bioisosterism: A Rational Approach in Drug Design. , 1996, Chemical reviews.
[12] B. Roth,et al. The discovery and development of atorvastatin, a potent novel hypolipidemic agent. , 2002, Progress in medicinal chemistry.
[13] W. R. Dolbier,et al. Fluorine chemistry at the millennium , 2005 .
[14] K. Kirk,et al. Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules , 2006 .
[15] A. Pike,et al. Fluorination of 3-(3-(piperidin-1-yl)propyl)indoles and 3-(3-(piperazin-1-yl)propyl)indoles gives selective human 5-HT1D receptor ligands with improved pharmacokinetic profiles. , 1999, Journal of medicinal chemistry.
[16] Paul Seiler,et al. A fluorine scan of thrombin inhibitors to map the fluorophilicity/fluorophobicity of an enzyme active site: evidence for C-F...C=O interactions. , 2003, Angewandte Chemie.
[17] D. Christianson,et al. Fluoroaromatic-fluoroaromatic interactions between inhibitors bound in the crystal lattice of human carbonic anhydrase II. , 2001, Journal of the American Chemical Society.
[18] E. Goldsmith,et al. Structural basis of inhibitor selectivity in MAP kinases. , 1998, Structure.
[19] D. O'Hagan,et al. Fluorine in medicinal chemistry: A review of anti-cancer agents , 2006 .
[20] D. Bonnet-Delpon,et al. Recent advances (1995–2005) in fluorinated pharmaceuticals based on natural products ☆ , 2006 .
[21] B. Fermini,et al. The impact of drug-induced QT interval prolongation on drug discovery and development , 2003, Nature Reviews Drug Discovery.
[22] Y. Shimohigashi,et al. Edge-to-face CH/pi interaction between ligand Phe-phenyl and receptor aromatic group in the thrombin receptor activation. , 2000, Journal of biochemistry.
[23] N. Kitteringham,et al. Metabolism of fluorine-containing drugs. , 2001, Annual review of pharmacology and toxicology.
[24] W. Middleton. New fluorinating reagents. Dialkylaminosulfur fluorides , 1975 .
[25] K. Drlica,et al. Fluoroquinolones: action and resistance. , 2003, Current topics in medicinal chemistry.
[26] Chu-Young Kim,et al. Contribution of Fluorine to Protein−Ligand Affinity in the Binding of Fluoroaromatic Inhibitors to Carbonic Anhydrase II , 2000 .
[27] D. Wong,et al. Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication. , 1995, Life sciences.
[28] D W Banner,et al. Molecular recognition at the thrombin active site: structure-based design and synthesis of potent and selective thrombin inhibitors and the X-ray crystal structures of two thrombin-inhibitor complexes. , 1997, Chemistry & biology.
[29] Bruce E. Smart,et al. Fluorine substituent effects (on bioactivity) , 2001 .
[30] G. Whitesides,et al. Thermodynamic parameters for the association of fluorinated benzenesulfonamides with bovine carbonic anhydrase II. , 2007, Chemistry, an Asian journal.
[31] B. Langlois,et al. Trifluoroacetamides from amino alcohols as nucleophilic trifluoromethylating reagents. , 2003, Angewandte Chemie.
[32] Z. Rankovic,et al. Medicinal chemistry of hERG optimizations: Highlights and hang-ups. , 2006, Journal of medicinal chemistry.
[33] M. Malet‐Martino,et al. Interest of Fluorine-19 Nuclear Magnetic Resonance Spectroscopy in the Detection, Identification and Quantification of Metabolites of Anticancer and Antifungal Fluoropyrimidine Drugs in Human Biofluids , 2006, Chemotherapy.
[34] Manfred Kansy,et al. Predicting and Tuning Physicochemical Properties in Lead Optimization: Amine Basicities , 2007, ChemMedChem.
[35] D. D. Perrin,et al. pKa prediction for organic acids and bases , 1981 .
[36] F. Diederich,et al. A fluorine scan of the phenylamidinium needle of tricyclic thrombin inhibitors: effects of fluorine substitution on pKa and binding affinity and evidence for intermolecular C-F...CN interactions. , 2004, Organic & biomolecular chemistry.
[37] M. Schlosser,et al. Alpha-fluorinated ethers, thioethers, and amines: anomerically biased species. , 2005, Chemical reviews.
[38] François Diederich,et al. Orthogonal multipolar interactions in structural chemistry and biology. , 2005, Angewandte Chemie.
[39] F. Diederich,et al. Interactions with aromatic rings in chemical and biological recognition. , 2003, Angewandte Chemie.
[40] D. Bundschuh,et al. Inhibition of airway hyperresponsiveness and pulmonary inflammation by roflumilast and other PDE4 inhibitors. , 2006, Pulmonary pharmacology & therapeutics.
[41] Dongsung Lim,et al. Inhibition of dipeptidyl peptidase IV (DPP IV) by 2-(2-amino-1-fluoro-propylidene)-cyclopentanecarbonitrile, a fluoroolefin containing peptidomimetic. , 2003, Bioorganic & medicinal chemistry.
[42] M. Bols,et al. Stereoelectronic substituent effects in polyhydroxylated piperidines and hexahydropyridazines. , 2002, Chemistry.
[43] F. Diederich,et al. Mapping the Fluorophilicity of a Hydrophobic Pocket: Synthesis and Biological Evaluation of Tricyclic Thrombin Inhibitors Directing Fluorinated Alkyl Groups into the P Pocket , 2006, ChemMedChem.
[44] J. Snyder,et al. The Unexpected Diaxial Orientation of cis-3,5-Difluoropiperidine in Water: A Potent CF- - -NH Charge-Dipole Effect , 2000 .
[45] F. Diederich,et al. A weak attractive interaction between organic fluorine and an amide group. , 2004, Angewandte Chemie.
[46] C. Moyes,et al. 3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT(2A) receptor antagonists. , 2001, Journal of medicinal chemistry.
[47] Robin Taylor,et al. Organic Fluorine Hardly Ever Accepts Hydrogen Bonds , 1997 .
[48] Manfred Kansy,et al. A Fluorine Scan at the Catalytic Center of Thrombin: CF, COH, and COMe Bioisosterism and Fluorine Effects on pKa and log D Values , 2006, ChemMedChem.
[49] G. Pez,et al. BIS(2-METHOXYETHYL)AMINOSULFUR TRIFLUORIDE : A NEW BROAD-SPECTRUM DEOXOFLUORINATING AGENT WITH ENHANCED THERMAL STABILITY , 1999 .
[50] Jun‐An Ma,et al. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions. , 2004, Chemical reviews.
[51] E. Pinard,et al. Discovery of 4-substituted-8-(2-hydroxy-2-phenyl-cyclohexyl)-2,8-diaza-spiro[4.5]decan-1-one as a novel class of highly selective GlyT1 inhibitors with improved metabolic stability. , 2006, Bioorganic & medicinal chemistry letters.
[52] J. Dunitz,et al. Molecular pair analysis: C-H...F interactions in the crystal structure of fluorobenzene? And related matters. , 2006, Chemistry.
[53] Manfred Kansy,et al. Multipolar interactions in the D pocket of thrombin: large differences between tricyclic imide and lactam inhibitors. , 2006, Organic & biomolecular chemistry.
[54] J. Snyder,et al. 3-Fluoropiperidines and N-methyl-3-fluoropiperidinium salts: the persistence of axial fluorine. , 2005, Chemistry.