Fluorine in medicinal chemistry

scientific article published on 13 December 2007

Fluorine in medicinal chemistry is …
instance of (P31):
review articleQ7318358
scholarly articleQ13442814

External links are
P356DOI10.1039/B610213C
P698PubMed publication ID18197348

P50authorVéronique GouverneurQ21716261
P2093author name stringPeter R Moore
Sophie Purser
Steve Swallow
P433issue2
P304page(s)320-330
P577publication date2007-12-13
P1433published inChemical Society ReviewsQ2962268
P1476titleFluorine in medicinal chemistry
P478volume37

Reverse relations

cites work (P2860)
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Q42221157Optimization of small-molecule inhibitors of influenza virus polymerase: from thiophene-3-carboxamide to polyamido scaffolds
Q39786216Optimizing the Physicochemical Properties of Raf/MEK Inhibitors by Nitrogen Scanning
Q52641759Organic synthesis provides opportunities to transform drug discovery.
Q42925133Organocatalytic Asymmetric Synthesis of Chiral Pyrrolizines by Cascade Conjugate Addition−Aldol Reactions
Q34158268Organocatalytic enantioselective olefin aminofluorination
Q41828750Organocatalyzed Trifluoromethylation of Ketones and Sulfonyl Fluorides by Fluoroform under a Superbase System
Q51778113Organofluorine Isoselenocyanate Analogues of Sulforaphane: Synthesis and Anticancer Activity.
Q37587813Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring.
Q42154307Oxidative 3,3,3-trifluoropropylation of arylaldehydes.
Q37678426Oxidative aliphatic C-H fluorination with manganese catalysts and fluoride ion
Q92426447Oxidative allene amination for the synthesis of nitrogen-containing heterocycles
Q59071306Palladium-Catalysed Synthesis of α-(Trifluoromethyl)styrenes by Means of Directed C-H Bond Functionalization
Q52685848Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides.
Q46495211Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3 as an Additive
Q61971329Palladium-Catalyzed Selective Synthesis of Perfluoroalkylated Enynes from Perfluoroalkyl Iodides and Alkynes
Q91635772Palladium-catalyzed coupling reactions on functionalized 2-trifluoromethyl-4-chromenone scaffolds. Synthesis of highly functionalized trifluoromethyl-heterocycles
Q41671171Palladium-catalyzed difluoromethylation of heteroaryl chlorides, bromides and iodides.
Q55634749Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides.
Q36147885Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.
Q35259134Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles
Q59071165Pd-Catalyzed Trifluoromethylthiolation of Unsaturated Compounds: A General Approach
Q42134444Pd-catalyzed C-H fluorination with nucleophilic fluoride
Q54948512Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers.
Q37637811Pd-catalyzed nucleophilic fluorination of aryl bromides
Q41990532Pd-catalyzed α-arylation of trimethylsilyl enolates of α,α-difluoroacetamides
Q38736425Pd-catalyzed α-arylation of α,α-difluoroketones with aryl bromides and chlorides. A route to difluoromethylarenes
Q36142192Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities
Q45935901Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides.
Q64989230Phosphatase CDC25B Inhibitors Produced by Basic Alumina-Supported One-Pot Gram-Scale Synthesis of Fluorinated 2-Alkylthio-4-aminoquinazolines Using Microwave Irradiation.
Q40555683Photo-organocatalytic Enantioselective Perfluoroalkylation of β-Ketoesters.
Q49339054Photocatalytic C-F Reduction and Functionalization
Q48345967Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.
Q42096518Photoredox catalysis: a mild, operationally simple approach to the synthesis of α-trifluoromethyl carbonyl compounds.
Q99579148Photosensitized direct C-H fluorination and trifluoromethylation in organic synthesis
Q42403853Practical and innate carbon-hydrogen functionalization of heterocycles
Q42123910Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).
Q55481533Prediction of 19F NMR Chemical Shifts for Fluorinated Aromatic Compounds.
Q59310247Preparation of 9α-Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities
Q36697709Preparation of o-Fluorophenols from Nonaromatic Precursors: Mechanistic Considerations for Adaptation to Fluorine-18 Radiolabeling
Q49740389Progress in copper-catalyzed trifluoromethylation
Q47726315Promiscuous Defluorinating Enoyl-CoA Hydratases/Hydrolases Allow for Complete Anaerobic Degradation of 2-Fluorobenzoate
Q82410435Property and Reactivity of Fluoro(silyl)acetylenes and Fluoro(stannyl)acetylenes
Q60953754Quantitative Assessment of rPM6 for Fluorine- and Chlorine-Containing Metal Complexes: Comparison with Experimental, First-Principles, and Other Semiempirical Results
Q91657582Quantum Chemical Lipophilicities of Antimalarial Drugs in Relation to Terminal Half-Life
Q61943020Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans
Q88948866Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification
Q102369571Radiosynthesis of [18F]SiFAlin-TATE for clinical neuroendocrine tumor positron emission tomography
Q52599217Radiosynthesis of the anticancer nucleoside analogue Trifluridine using an automated 18F-trifluoromethylation procedure.
Q55021811Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies.
Q46093462Rapid access to β-trifluoromethyl-substituted ketones: harnessing inductive effects in Wacker-type oxidations of internal alkenes.
Q37418628Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system
Q37446492Rapid cycloaddition of a diazo group with an unstrained dipolarophile
Q87624590Rapid trifluoromethylation and perfluoroalkylation of five-membered heterocycles by photoredox catalysis in continuous flow
Q36096683Rational Design of Orthogonal Multipolar Interactions with Fluorine in Protein-Ligand Complexes
Q64067588Recent Advances for the Direct Introduction of the CFMe Moiety
Q92582415Recent Development of Catalytic Trifluoromethoxylation Reactions
Q37406266Recent advances in transition metal-catalyzed Csp(2)-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation
Q90618746Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups
Q90380407Recent developments in photoredox-catalyzed remote ortho and para C-H bond functionalizations
Q55339854Redox-ligand sustains controlled generation of CF3 radicals by well-defined copper complex.
Q42157743Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates
Q101133084Regioselective Markovnikov hydrodifluoroalkylation of alkenes using difluoroenoxysilanes
Q87429316Regioselective trifluoromethylation of N-heteroaromatic compounds using trifluoromethyldifluoroborane activator
Q35598226Removal of Metabolic Liabilities Enables Development of Derivatives of Procaspase-Activating Compound 1 (PAC-1) with Improved Pharmacokinetics
Q34264792Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides
Q41640907Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds.
Q36266419Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization
Q38974125Room temperature, metal-free arylation of aliphatic alcohols
Q36499563Ruthenium(II) Complexes with 2-Phenylimidazo[4,5-f][1,10]phenanthroline Derivatives that Strongly Combat Cisplatin-Resistant Tumor Cells
Q52345612Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives.
Q28543910SD-208, a novel protein kinase D inhibitor, blocks prostate cancer cell proliferation and tumor growth in vivo by inducing G2/M cell cycle arrest
Q92338239Selective C-F Functionalization of Unactivated Trifluoromethylarenes
Q41502645Selective and Scalable Perfluoroarylation of Nitroalkanes
Q47232071Selective radical trifluoromethylation of native residues in proteins.
Q39312759Semisynthetic ursolic acid fluorolactone derivatives inhibit growth with induction of p21(waf1) and induce apoptosis with upregulation of NOXA and downregulation of c-FLIP in cancer cells
Q39873974Separation of Fluorinated Amino Acids and Oligopeptides from their Non-fluorinated Counterparts using High-performance Liquid Chromatography
Q42741143Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins
Q92134474Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water
Q39172790Silver-mediated trifluoromethoxylation of aryl stannanes and arylboronic acids.
Q39547245Silver-mediated trifluoromethylation of arenes using TMSCF3.
Q91151044Stereocontrolled Synthesis of 2-Fluorinated C-Glycosides
Q52314785Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes.
Q37118304Stereoselective synthesis of conjugated fluoro enynes
Q43086626Sterically Demanding Unsymmetrical Diaryl-λ(3)-iodanes for Electrophilic Pentafluorophenylation and an Approach to α-Pentafluorophenyl Carbonyl Compounds with an All-Carbon Stereocenter
Q93107245Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas
Q27664447Structural and Biochemical Studies of a Fluoroacetyl-CoA-Specific Thioesterase Reveal a Molecular Basis for Fluorine Selectivity
Q89768852Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(penta-fluoro-λ6-sulfan-yl)benzo-nitrile
Q36624204Structure-Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N'-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists
Q39489607Structure-activity relationships in tripodal transmembrane anion transporters: the effect of fluorination
Q36724814Studies toward the oxidative and reductive activation of C-S bonds in 2'-S-aryl-2'-thiouridine derivatives.
Q34489910Studying regioisomer formation in the Pd-catalyzed fluorination of aryl triflates by deuterium labeling
Q39148610Substituted 3-benzylcoumarins as allosteric MEK1 inhibitors: design, synthesis and biological evaluation as antiviral agents.
Q92927794Substrate-Controlled Product Divergence: Silver-Catalyzed Reaction of Trifluoromethyl Ketones with Terminal Alkynes
Q41586778Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester
Q88663589Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture
Q38740264Synthesis and In Vitro Cytotoxic Properties of Polycarbo-Substituted 4-(Arylamino)quinazolines.
Q46526956Synthesis and In Vitro Cytotoxicity of the 4-(Halogenoanilino)-6-bromoquinazolines and Their 6-(4-Fluorophenyl) Substituted Derivatives as Potential Inhibitors of Epidermal Growth Factor Receptor Tyrosine Kinase
Q37664921Synthesis and SAR studies of dual AKT/NF-κB inhibitors against melanoma
Q34503993Synthesis and anticancer activity evaluation of 3,4-mono- and bicyclosubstituted N-(het)aryl trifluoromethyl succinimides
Q28595401Synthesis and antiviral evaluation of 2′,2′,3′,3′-tetrafluoro nucleoside analogs
Q47134152Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines
Q41896301Synthesis and applications of α-trifluoromethylated alkylboron compounds
Q42802652Synthesis and biological evaluation of novel urea- and guanidine-based derivatives for the treatment of obesity-related hepatic steatosis.
Q42237305Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes.
Q47983429Synthesis and structure-activity studies on novel analogs of human growth hormone releasing hormone (GHRH) with enhanced inhibitory activities on tumor growth
Q92928783Synthesis of 3-CF2-Containing Chromones via a Visible-Light-Induced Radical Cascade Reaction of o-Hydroxyaryl Enaminones
Q89966313Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C-F···H-C bonds
Q41972307Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling
Q62032080Synthesis of Fluorinated Leishmania Cap Trisaccharides for Diagnostic Tool and Vaccine Development
Q59478311Synthesis of Fluoroalkyl Pyrazoles from In-Situ-Generated C2F5CHN2and Electron-Deficient Alkenes
Q89857941Synthesis of Fulvene Vinyl Ethers by Gold Catalysis
Q52340414Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil.
Q42365816Synthesis of Trifluoromethoxylated (Hetero)Arenes via OCF3 Migration.
Q59353282Synthesis of Trifluoromethyl-α,β-unsaturated Lactones and Pyrazolinones and Discovery of Influenza Virus Polymerase Inhibitors
Q92860159Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy
Q97543864Synthesis of antiviral perfluoroalkyl derivatives of teicoplanin and vancomycin
Q89941005Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes
Q58769313Synthesis of chiral α-trifluoromethyl alcohols and ethers via enantioselective Hiyama cross-couplings of bisfunctionalized electrophiles
Q92823731Synthesis of difluoromethylated allenes through trifunctionalization of 1,3-enynes
Q64238170Synthesis of enantiopure F-trifluoromethyl cysteine as a structure-mimetic amino acid tracer for glioma imaging
Q52728708Synthesis of fluoro-functionalized diaryl-λ3-iodonium salts and their cytotoxicity against human lymphoma U937 cells.
Q38841376Synthesis of new indole-based bisphosphonates and evaluation of their chelating ability in PE/CA-PJ15 cells
Q41914414Synthesis of trifluoromethylated isoxazolidines: 1,3-dipolar cycloaddition of nitrosoarenes, (trifluoromethyl)diazomethane, and alkenes
Q48119060Synthesis of α-Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
Q47714197Synthesis, Cytotoxicity and Molecular Docking Studies of the 9-Substituted 5-Styryltetrazolo[1,5-c]quinazoline Derivatives.
Q58697246Synthesis, Evaluation for Cytotoxicity and Molecular Docking Studies of Benzo[]furan-Chalcones for Potential to Inhibit Tubulin Polymerization and/or EGFR-Tyrosine Kinase Phosphorylation
Q53077899Synthesis, Fungicidal Activity and Mode of Action of 4-Phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea.
Q90192725Synthesis, In Vitro Evaluation and Molecular Docking of the 5-Acetyl-2-aryl-6-hydroxybenzo[b]furans against Multiple Targets Linked to Type 2 Diabetes
Q42927838Synthesis, Spectral Characterization, In-vitro Antibacterial and Antifungal Activities of Novel (2e)-Ethyl-2-(2-(2, 4-Dinitrophenyl) Hydrazono)-4-(Naphthalen-2-yl)-6-Arylcyclohex-3-Enecarboxylates
Q92029231Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking study of novel inhibitor of hepatitis B: methyl 4-fluoro-3-(morpholinosulfonyl)benzo[b]thiophene-2-carboxylate
Q61450167Synthesis, biophysical properties, and RNase H activity of 6'-difluoro[4.3.0]bicyclo-DNA
Q34053493Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides
Q28834646Synthetic biology approaches to fluorinated polyketides
Q92271463Systematic Hydrogen-Bond Manipulations To Establish Polysaccharide Structure-Property Correlations
Q42291702Targeted Fluoro Positioning for the Discovery of a Potent and Highly Selective Matrix Metalloproteinase Inhibitor
Q87185992Targeted fluorination of a nonsteroidal anti-inflammatory drug to prolong metabolic half-life
Q58211551Targeting Carbonic Anhydrases with Fluorescent BODIPY-Labelled Sulfonamides
Q37579319Targeting the Endocannabinoid System for Neuroprotection: A (19)F-NMR Study of a Selective FAAH Inhibitor Binding with an Anandamide Carrier Protein, HSA.
Q37760799The C-F bond as a conformational tool in organic and biological chemistry
Q90274970The Journey of HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) from Lab to Clinic
Q50545600The Magnesium(II)‐Catalyzed Asymmetric Ketone–Ene Reaction under Solvent‐Free Conditions: Stereocontrolled Access to Enantioenriched Trifluoromethyl‐Substituted Compounds
Q41879986The difluoromethylene (CF2) group in aliphatic chains: Synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups
Q87431567The direct anti-Markovnikov addition of mineral acids to styrenes
Q42293575The dual role of thiourea in the thiotrifluoromethylation of alkenes.
Q35623583The palladium-catalyzed trifluoromethylation of vinyl sulfonates
Q34105033The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective alpha-trifluoromethylation of aldehydes
Q84262951The role of fluorine atoms in a fluorinated prostaglandin agonist
Q46011455The role of fluorine in stabilizing the bioactive conformation of dihydroorotate dehydrogenase inhibitors.
Q55275345The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives.
Q36551437The toxicity of the N-hydroxy and 6-hydroxy metabolites of 3,4-dichloropropionanilide does not depend on calcium release-activated calcium channel inhibition
Q56603992The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research
Q42383517Themed series in organo-fluorine chemistry
Q47898057Theoretical Study on the Conformational Bioeffect of the Fluorination of Acetylcholine
Q49508703Theoretical models of inhibitory activity for inhibitors of protein–protein interactions: targeting menin–mixed lineage leukemia with small molecules
Q39647534Three step synthesis of single diastereoisomers of the vicinal trifluoro motif
Q35031035Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
Q64027903Transition-Metal-Free Radical Hydrotrifluoromethylation of Alkynes
Q58623742Transition-Metal-Free Regioselective C-H Bond Fluorination of 8-Amidoquinolines with Selectfluor
Q38244526Transitioning organic synthesis from organic solvents to water. What's your E Factor?
Q37158035Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ]
Q52641964Trifluoromethylation of Secondary Nitroalkanes.
Q34239799Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis.
Q64024268Trifluoromethylthiolation of Unsymmetrical λ3-Iodane Derivatives: Additive-Free, Selective and Scalable Introduction of the SCF3Group
Q59071175Trifluoromethylthiolation of α-Chloroaldehydes: Access to Quaternary SCF3 -Containing Centers
Q33572194Trisubstituted 2-trifluoromethyl pyrrolidines via catalytic asymmetric Michael addition/reductive cyclization
Q89518882Use of α-trifluoromethyl carbanions for palladium-catalysed asymmetric cycloadditions
Q41013531Vanadium-Catalyzed C(sp(3))-H Fluorination Reactions
Q88948863Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles
Q28286045Visible light photocatalysis as a greener approach to photochemical synthesis
Q34333964Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis
Q55712381Visible light-mediated difluoroalkylation of electron-deficient alkenes.
Q42773523Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination
Q47375033Visible-Light Photocatalytic Decarboxylation of α,β-Unsaturated Carboxylic Acids: Facile Access to Stereoselective Difluoromethylated Styrenes in Batch and Flow
Q93002953Visible-light Promoted Atom Transfer Radical Addition-Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-Donor
Q42285443Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water
Q60915719eToxPred: a machine learning-based approach to estimate the toxicity of drug candidates
Q62784517α-Fluorination of carbonyls with nucleophilic fluorine
Q48219710α-Fluoro-o-cresols: The Key Role of Intramolecular Hydrogen Bonding in Conformational Preference and Hydrogen-Bond Acidity
Q47106655α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration.
Q62073093β-Lactam Bioconjugates Bearing Luminescent Platinum(II) Tags: Synthesis and Photophysical Characterization
Q90025889ω-Phthalimidoalkyl Aryl Ureas as Potent and Selective Inhibitors of Cholesterol Esterase

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