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Review

Polyfluorinated Groups in Medicinal Chemistry

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Pages 527-546 | Published online: 15 Apr 2015

References

  • Meanwell N A . Synopsis of some recent tactical application of bioisosteres in drug design. J. Med. Chem.54 (8), 2529–2591 (2010).
  • Wang J , Sánchez-RosellóM, AceñaJ L, Al.E. Fluorine in pharmaceutical industry fluorine-containing drugs introduced to the market in the last decade 2001–2011. Chem. Rev.114 (4), 2432–2506 (2014).
  • Purser S , MooreP R, SwallowS, GouverneurV. Fluorine in medicinal chemistry. Chem. Soc. Rev.37, 320–330 (2008).
  • O'hagan D , HarperD B. Fluorine-containing natural products. J. Fluor. Chem.100 (1–2), 127–133 (1999).
  • Smart B E . Fluorine substituent effects on bioactivity. J. Fluor. Chem.109 (1), 3–11 (2001).
  • Hansch C , LeoA. Exploring QSAR. Fundamentals And Applications In Chemistry And Biology.American Chemical Society, Washington, DC, (1995).
  • Hansch C , LeoA, HoekmanD. Exploring QSAR. Hydrophobic, Electronic And Steric Constants.ACS Professional Reference Book, American Chemical Society, Washington, DC, (1995).
  • Leo A , HanschC, ElkinsD. Partition coefficients and their uses. Chem. Rev.71 (6), 525–616 (1971).
  • Hansch C , LeoA, UngerS H, KimK H, NikaitaniD, LienE J. Aromatic substituent constants for structure activity correlations. J. Med. Chem.16 (11), 1207–1216 (1973).
  • Hansch C , LeoA, TaftRW. A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev.91 (2), 165–195 (1991).
  • Dalvit C , VulpettiA. Intermolecular and intramolecular hydrogen bonds involving fluorine atoms implications for recognition, selectivity, and chemical properties. ChemMedChem7 (2), 262–272 (2012).
  • Zhu W , WangJ, WangSet al. Recent advances in the trifluoromethylation methodology and new CF3-containing drugs. J. Fluor. Chem.167 (0), 37–54 (2014).
  • Tlili A , BillardT. Formation of C-SCF3 bonds through direct trifluoromethylthiolation. Angew. Chem. Int. Ed.52 (27), 6818–6819 (2013).
  • Yagupol'skii LM . Dokl. Akad. Nauk SSSR105, 100–102 (1955).
  • Umemoto T , AdachiK, IshiharaS. CF3-Oxonium Salts, O-(Trifluoromethyl)dibenzofuranium Salts: In situ Synthesis, Properties, and Application as a Real CF+ Species ReagentJ. Org. Chem.72, 6905–6917 (2007).
  • Koller R , StanekK, StolzD, AardoomR, NiedermannK, TogniA. Zinc Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents. Angew. Chem. Int. Ed.48, 4332–4336 (2009).
  • Feiring A E , RozenS, WonchobaER. Synthesis of arylperfluoroalkyl ethers by direct fluorination. J. Fluor. Chem.34 (1998), (1998).
  • Leroux F R , ManteauB, VorsJ P, PazenokS. Trifluoromethyl ethers – synthesis and properties of an unusual substituent. Beil. J. Org. Chem.15 (2008), (2008).
  • T.U: US7592491B2 (2010).
  • Frischmuth A , UnsinnA, GrollK, StadtmüllerH, KnochelP. Preparations and reactions of SF5-substituted aryl and heteroaryl derivatives via Mg and Zn organometallics. Chem. Eur. J.18 (33), 10234–10238 (2012).
  • Bowden B D , CominaP J, GreenhallM P, KariukiB M, LovedayA, PhilpD. A new method for the synthesis of aromatic sulfurpentafluorides and studies of the stability of the sulfur pentafluoride group in common synthetic transformations. Tetrahedron56 (21), 3399–3408 (2000).
  • Brel V K . Synthesis and Diels-Alder reactions of dienophiles with pentafluoro-λ6-sulfanyl (SF5) moiety. Synthesis2, 339–343 (2006).
  • Brel V K . Synthesis of 4,5-Dihydroisoxazoles connected by short spacers to the pentafluoro-λ6-sulfanyl group. Synthesis (16), 2665–2267 (2006).
  • Savoie PR , WelchJT. Preparation and Utility of Organic Pentafluorosulfanyl-Containing CompoundsChem. Rev. DOI: 10.1021/cr500336u (2014).
  • Wishart D S , KnoxC, GuoAC, Al.E. DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acid Res.36, D901–D906 (2007).
  • Crockett M , KainK C. Tafenoquine: a promising new antimalarial agent. Expert Opin. Inv. Drugs16, 705–715 (2007).
  • Dhammika N , AgerA L J, BartlettM, Al.E. Antiparasitic activities and toxicities of individual enantiomers of the 8-aminoquinoline 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3,4-dichlorophenoxy]quinoline succinateAntimicrob. Agents Chemother6, 2130–2137 (2008).
  • Lucking U , JautelatR, KrugerMet al. The lab oddity prevails discovery of pan-CDK inhibitor R -S-cyclopropyl-S- 4-{[4-{[1R,2R -2-hydroxy-1-methylpropyl]oxy}-5- trifluoromethyl pyrimidin-2-yl]amino}phenyl sulfoximide BAY-1000394 for the treatment of cancer. ChemMedChem8 (7), 1067–1085 (2013).
  • Watanabe Y , AsaiH, IshiiT, Al.E. Pharmacological characterization of T-2328, 2-fluoro-4 ‘-methoxy-3′-2S,3S-2-phenyl-3-piperidinyl amino methyll 1,1′-biphenyl-4-carbonitrile dihydrochloride, as a brain-penetrating antagonist of tachykinin NK1 receptor. J. Pharmacol. Sci.106 (1), 121–127 (2008).
  • Kim D , WangL, BeconiM, EiermannGJ, Al.E. 2R-4-Oxo-4-[3-trifluoromethyl-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7,8H-yl]-1–2,4,5-trifluorophenyl butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of Type 2 diabetes. J. Med. Chem.48 (1), 141–151 (2005).
  • Mccormck PL . Celecoxib a review of its use for symptomatic relief in the treatment of osteoarthritis, rheumatoid arthritis and ankylosing spondylitis. Drugs71 (18), 2457–2489 (2011).
  • Lindberg P , CarlssonE. Esomeprazole in the framework of proton-pump inhibitor development. In : Analogue-based Drug Discovery.Wiley-VCH Verlag GmbH & Co.KGaA, 81–113 (2006).
  • Satoh H . Discovery of lansoprazole and its unique pharmacological properties independent from anti-secretory activity. Curr. Pharm. Design19 (1), 67–75 (2013).
  • Kubo K , OdaK, KanekoT, SatohH, NoharaA. Synthesis of 2,4-fluoroalkoxy-2-pyridylmethyl]sulfinyl]-1H-benzimidazoles as antiulcer agents. Chem. Bull. Pharm.38 (10), 2853–2858 (1990).
  • Senn-Bilfinger J , SturmE. The development of a new proton-pump inhibitor: the case history of pantoprazole. In : Analogue-based Drug Discovery.Wiley-VCH Verlag GmbH & Co.KGaA. 115–136 (2006).
  • Yuasa K , KanohY, OkumuraK, OmoriK. Genomic organization of the human phosphodiesterase PDE11A gene. Evolutionary relatedness with other PDEs containing GAF domains. Eur. J. Biochem.268 (1), 168–178 (2001).
  • Soderling S H , BeavoJA. Regulation of cAMP and cGMP signaling: new phosphodiesterases and new functions. Curr. Opin. Cell. Biol.12 (2), 174–179 (2000).
  • Guay D , HamelP, BlouinMet al. Discovery of L-791943 A potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor. Bioorg. Med. Chem. Lett.12 (11), 1457–1461 (2002).
  • Hansch C , LeoA. Substituent Constants For Correlation Analysis In Chemistry And Biology.Wiley, New York, NY339 (1979).
  • Tse C , ShoemakerA R, AdickesJet al. ABT-263 A potent and orally bioavailable Bcl-2 family inhibitor. Cancer Res.68 (9), 3421–3428 (2008).
  • Petros A M , DingesJ, AugeriD Jet al. Discovery of a potent inhibitor of the antiapoptotic protein Bcl-xL from NMR and parallel synthesis. J. Med. Chem.49 (2), 656–663 (2006).
  • Wendt M D , ShenW, KunzerA. Discovery and structure?activity relationship of antagonists of B Cell lymphoma. J. Med. Chem.49 (3), 1165–1181 (2006).
  • Bruncko M , OostT K, BelliB Aet al. Studies leading to potent, dual inhibitors of Bcl-2 and Bcl-xL. J. Med. Chem.50 (4), 641–662 (2007).
  • Park C M , BrunckoM, AdickesJet al. Discovery of an orally bioavailable small molecule inhibitor of prosurvival B-Cell Lymphoma 2 proteins. J. Med. Chem.51 (21), 6902–6915 (2008).
  • Kuo E A , HambletonP T, KayD Pet al. Synthesis, structure-activity relationships, and pharmacokinetic properties of dihydroorotate dehydrogenase inhibitors: 2-cyano-3-cyclopropyl-3-hydroxy-N-[3′-methyl-4′-(trifluoromethyl) phenyl]propenamide and related compounds. J. Med. Chem.39 (23), 4608–4621 (1996).
  • Gard G L . Recent milestone in SF5-chemistry. Chem. Today27, 10–13 (2009).
  • Altomonte S , ZandaM. Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules. J. Fluor. Chem.143, 57–93 (2012).
  • Verma R , KirchmeierR, ShreeveJ. Advances in Inorganic Chemistry.Elsevier125–169 (1994).
  • Lentz D , SeppeltK. The SF5, SeF5 and TeF5 groups in organic chemistry. In : Chemistry of Hypervalent Compounds.Wiley VCH, New York, NY 323(1999), (1999).
  • Sæthre L J , BerrahN, BozekJ D. Chemical insights from high resolution X ray photoelectron spectroscopy and ab initio theory: propyne, trifluoropropyne, and ethylsulfur pentafluoride. J. Am. Chem. Soc.123, 10729–10737 (2001).
  • Jackson DA , MaburySA. Breaking down the substituent of the future: environmental properties of pentafluorosulfanyl compounds. Presented at : 236th ACS National Meeting. Philadelphia, PA, USA, August, (2008).
  • Masereel L , PochetL, LaeckmannD. An overview of inhibitors of Na+/H+ exchanger. Eur. J. Med. Chem.38 (6), 547–554 (2003).
  • Scholz W , AlbusU, LangH, Al.E. Hoe 694, a new Na+/H+ exchange inhibitor and its effects in cardiac ischaemia. Br. J. Pharmacol.109 (2), 562–568 (1993).
  • Kleemann H W: US2003216476, (2003).
  • Kleemann H W: US2005043401, (2005).
  • Fairlamb A H , BlackburnP, UlrichP, ChaitB T, CeramiA. Trypanothione a novel bis glutathionyl spermidine cofactor for glutathione reductase in trypanosomatids. Science227 (4693), 1485–1487 (1985).
  • Parveen S , KhanM O F, AustinS Eet al. Antitrypanosomal, antileishmanial, and antimalarial activities of quaternary arylalkylammonium 2-amino-4-chlorophenyl phenyl sulfides, a new class of trypanothione reductase inhibitor, and of N-acyl derivatives of 2-amino-4-chlorophenyl phenyl sulfide. J. Med. Chem.48 (25), 8087–8097 (2005).
  • Stump B , EberleC, SchweizerW B. Pentafluorosulfanyl as a novel building block for enzyme inhibitors: Trypanothione Reductase inhibition and antiprotozoal activities of diarylamines. ChemBioChem10 (1), 79–83 (2009).
  • Tokoyama A , NakaiY, YonedaS, KuritaY, NiitaniH. Activity of gemcitabine in the treatment of patients with non small cell lung cancer: a multicenter phase II study. Anti Cancer Drugs8 (6), 574–581 (1997).
  • Prakash G K S , ZibinskyM, UptonT G, Al.E. Synthesis and biological evaluation of fluorinated deoxynucleotide analogs based on bis-(difluoromethylene)triphosphoric acid. Proc Natl Acad. Sci. USA107 (36), 15693–15698 (2010).
  • Shakhmin A , JonesJ-P, BychinskayaIet al. Preparation of fluorinated RNA nucleotide analogs potentially stable to enzymatic hydrolysis in RNA and DNA polymerase assays. J. Fluor. Chem.167 (0), 226–230 (2014).
  • Santner T , RiederU, KreutzC, MicuraR. Pseudoknot Preorganization of the PreQ1 Class I Riboswitch. J. Am. Chem. Soc.134 (29), 11928–11931 (2012).
  • Košutić M , JudL, Da VeigaC, Al.E. Surprising base pairing and structural properties of 2′-trifluoromethylthio-modified ribonucleic acids. J. Am. Chem. Soc.136 (18), 6656–6663 (2014).
  • Campbell M A , WengelJ. Locked vs. unlocked nucleic acids (LNA vs. UNA): contrasting structures work towards common therapeutic goals. Chem. Soc. Rev.40, 5680–5689 (2011).
  • Houston M E, Jr, VanderJ D L, HonekJF. Synthesis and biological activity of fluorinated intermediates of the methionine salvage pathway. Bioorg. Med. Chem. Lett.1 (11), 623–628 (1991).
  • Joseph E C , ReesJ A, DayanA. Mesenteric Arteriopathy in the rat induced by phosphodiesterase III inhibitors: an investigation of morphological, ultrastructural, and hemodynamic changes. Toxicol. Pathol.24, 436–450 (1996).
  • Bavetsias V , SunC, BoulocNet al. Hit generation and exploration: Imidazo[4,5-b]pyridine derivatives as inhibitors of Aurora kinases. Bioorg. Med. Chem. Lett.17 (23), 6567–6571 (2007).
  • Iaroshenko V O , OstrovskyiD, PetrosyanA, MkrtchyanS, VillingerA, LangerP. Synthesis of fluorinated purine and 1-deazapurine glycosides as potential inhibitors of adenosine deaminase. J. Org. Chem.76 (8), 2899–2903 (2011).
  • Drexler J , GrothU. Trifluoromethylated Nucleosides: A building block approach to cytotoxic adenosine analogues. Eur. J. Org. Chem.28, 6314–6320 (2014)
  • Martin J C , McgeeD P, JeffreyG A. Synthesis and anti-herpes virus activity of acyclic 2′-deoxyguanosine analogs related to 9-[1,3-dihydroxy-2-propoxy methyl]guanine. J. Med. Chem.29 (8), 1384–1389 (1986).
  • Harnden M R , JarvestR L, BaconT H, BoydM R. Synthesis and antiviral activity of 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purinesJ. Med. Chem.30 (9), 1636–1642 (1987).
  • Hospers G A , CalogeroA, Van WaardeA. Monitoring of herpes simplex virus thymidine kinase enzyme activity using positron emission tomography. Cancer Res.60 (6), 1488–1491 (2000).
  • De Vries EF , Van WaardeA, HarmsenM C, MulderN H, VaalburgW, HospersG A. [11C]. FMAU and [18F]FHPG as PET tracers for herpes simplex virus thymidine kinase enzyme activity and human cytomegalovirus infections. Nucl. Med. Biol.27 (2), 113–119 (2000).
  • Alauddin M M , ContiP S. Synthesis and preliminary evaluation of 9-(4-[18F]-fluoro-3-hydroxymethylbutyl)guanine ([18F]FHBG): A new potential imaging agent for viral infection and gene therapy using PET. Nucl. Med. Biol.25 (3), 175–180 (1998).
  • Prekupec S , MakucD, PlavecJet al. Novel C-6 fluorinated acyclic side chain pyrimidine derivatives? synthesis, 1H and 13C NMR conformational studies, and antiviral and cytostatic evaluations. J. Med. Chem.50 (13), 3037–3045 (2007).
  • Crank G , HardingD R K, SzinaiS S. Perfluoroalkyl carbonyl compounds. J. Med. Chem. Perfluoroaldehyde and perfluorocarboxylic acid derivatives. 13 (6), 1212–1215 (1970).
  • Trivedi B K , BridgesA J, PattW C, PriebeS R, BrunstR F. Perfluoroalkyl carbonyl compounds. 1. Perfluoro-N-[4-(1H-tetrazol-5-ylmethyl)phenyl]-alkanamides. A new class of oral antidiabetic agents. J. Med. Chem.32 (1), 11–13 (1989).
  • The SF5 substituent: Useful in medicinal chemistry or not? https://www.linkedin.com/groups/SF5-substituent-Useful-in-medicinal-923867. S. 5801795069040148483

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