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Volumn , Issue , 2014, Pages 1-54

Tactical applications of fluorine in drug design and development

Author keywords

Fluorine and basicity; Fluorine and conformation; Fluorine and hydrogen bonding; Fluorine and membrane permeability; Fluorine and metabolic stability; Gauche interaction; Positron emitting tomography imaging

Indexed keywords

AMINES; HYDROGEN BONDS; METABOLISM; PHYSICOCHEMICAL PROPERTIES; POSITRONS; TOMOGRAPHY;

EID: 84947203195     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-319-04346-3_1     Document Type: Chapter
Times cited : (11)

References (201)
  • 1
    • 70349124638 scopus 로고    scopus 로고
    • Design and nmr-based screening of lef, a library of chemical fragments with different local environments of fluorine
    • Vulpetti A, Hommel U, Landrum G, Lewis R, Dalvit C (2009) Design and NMR-based screening of LEF, a library of chemical fragments with different local environments of fluorine. J Am Chem Soc 131:12949–12959
    • (2009) J am Chem Soc , vol.131 , pp. 12949-12959
    • Vulpetti, A.1    Hommel, U.2    Landrum, G.3    Lewis, R.4    Dalvit, C.5
  • 3
    • 84864633171 scopus 로고    scopus 로고
    • Fluorine local environments: From screening to drug design
    • Vulpetti A, Dalvit C (2012) Fluorine local environments: from screening to drug design. Drug Discov Today 17:890–897
    • (2012) Drug Discov Today , vol.17 , pp. 890-897
    • Vulpetti, A.1    Dalvit, C.2
  • 6
    • 84944641603 scopus 로고
    • Gutmann V, Academic, New York
    • Sharpe AG (1967) In: Gutmann V (ed) Halogen chemistry, vol 1. Academic, New York, p 12
    • (1967) Halogen Chemistry , vol.1 , pp. 12
    • Sharpe, A.G.1
  • 9
    • 33750813038 scopus 로고    scopus 로고
    • Recent developments on the fluorinase of streptomyces cattleya
    • O’Hagan D (2006) Recent developments on the fluorinase of streptomyces cattleya. J Fluor Chem 127:1479–1483
    • (2006) J Fluor Chem , vol.127 , pp. 1479-1483
    • O’Hagan, D.1
  • 11
    • 65349170600 scopus 로고    scopus 로고
    • Biohalogenation: Nature’s way to synthesize halogenated metabolites
    • Wagner C, El Omari M, König GM (2009) Biohalogenation: nature’s way to synthesize halogenated metabolites. J Nat Prod 72:540–553
    • (2009) J Nat Prod , vol.72 , pp. 540-553
    • Wagner, C.1    El Omari, M.2    König, G.M.3
  • 12
    • 0010188925 scopus 로고
    • Rare fluorinated natural products
    • Meyer M, O’Hagan D (1992) Rare fluorinated natural products. Chem Br 28:785
    • (1992) Chem Br , vol.28 , pp. 785
    • Meyer, M.1    O’Hagan, D.2
  • 16
    • 34848848499 scopus 로고    scopus 로고
    • Fluorine in pharmaceuticals: Looking beyond intuition
    • Müller K, Faeh C, Diederich F (2007) Fluorine in pharmaceuticals: looking beyond intuition. Science 317:1881–1886
    • (2007) Science , vol.317 , pp. 1881-1886
    • Müller, K.1    Faeh, C.2    Diederich, F.3
  • 17
    • 49449097238 scopus 로고    scopus 로고
    • The many roles for fluorine in medicinal chemistry
    • Hagmann WK (2008) The many roles for fluorine in medicinal chemistry. J Med Chem 51:4359–4369
    • (2008) J Med Chem , vol.51 , pp. 4359-4369
    • Hagmann, W.K.1
  • 19
    • 35348938545 scopus 로고    scopus 로고
    • The role of fluorine in medicinal chemistry
    • Shah P, Westwell AD (2007) The role of fluorine in medicinal chemistry. J Enzym Inhib Med Chem 22:527–540
    • (2007) J Enzym Inhib Med Chem , vol.22 , pp. 527-540
    • Shah, P.1    Westwell, A.D.2
  • 20
    • 38149016915 scopus 로고    scopus 로고
    • Understanding organofluorine chemistry: An introduction to the c-f bond
    • O’Hagan D (2008) Understanding organofluorine chemistry: an introduction to the C-F bond. Chem Soc Rev 37:308–319
    • (2008) Chem Soc Rev , vol.37 , pp. 308-319
    • O’Hagan, D.1
  • 21
    • 77952688640 scopus 로고    scopus 로고
    • The c-f bond as a conformational tool in organic and biological chemistry
    • Hunter L (2010) The C-F bond as a conformational tool in organic and biological chemistry. Belistein J Org Chem 6. doi:103762/bjoc.6.38
    • (2010) Belistein J Org Chem , pp. 6
    • Hunter, L.1
  • 22
    • 83455243028 scopus 로고    scopus 로고
    • Fluorine conformational effects in organocatalysis: An emerging strategy for molecular design
    • Zimmer LE, Sparr C, Gilmour R (2011) Fluorine conformational effects in organocatalysis: an emerging strategy for molecular design. Angew Chem Int Ed 50:11860–11871
    • (2011) Angew Chem Int Ed , vol.50 , pp. 11860-11871
    • Zimmer, L.E.1    Sparr, C.2    Gilmour, R.3
  • 23
    • 76749091475 scopus 로고    scopus 로고
    • A dft study on the origin of the fluorine gauche effect in substituted fluoroethanes
    • Buissonneaud DY, van Mourik T, O’Hagan D (2010) A DFT study on the origin of the fluorine gauche effect in substituted fluoroethanes. Tetrahedron 66:2196–2202
    • (2010) Tetrahedron , vol.66 , pp. 2196-2202
    • Buissonneaud, D.Y.1    Van Mourik, T.2    O’Hagan, D.3
  • 24
    • 84860131849 scopus 로고    scopus 로고
    • Organofluorine chemistry: Synthesis and conformation of vicinal fluoromethylene motifs
    • O’Hagan D (2012) Organofluorine chemistry: synthesis and conformation of vicinal fluoromethylene motifs. J Org Chem 77:3689–3699
    • (2012) J Org Chem , vol.77 , pp. 3689-3699
    • O’Hagan, D.1
  • 25
    • 0342569315 scopus 로고    scopus 로고
    • Conformational properties of 1,3-difluoropropane
    • Wu D, Tian A, Sun H (1998) Conformational properties of 1,3-difluoropropane. J Chem Phys A 102:9901–9905
    • (1998) J Chem Phys A , vol.102 , pp. 9901-9905
    • Wu, D.1    Tian, A.2    Sun, H.3
  • 26
    • 0037161862 scopus 로고    scopus 로고
    • The fluorine gauche effect. Langmuir isotherms report the relative conformational stability of (±)- erythro - and (±)- threo -9,10-difluorostearic acids
    • Tavasli M, O’Hagan D, Pearson C, Petty MC (2002) The fluorine gauche effect. Langmuir isotherms report the relative conformational stability of (±)- erythro - and (±)- threo -9,10-difluorostearic acids. Chem Commun 1226–1227
    • (2002) Chem Commun , pp. 1226-1227
    • Tavasli, M.1    O’Hagan, D.2    Pearson, C.3    Petty, M.C.4
  • 27
    • 70349779000 scopus 로고    scopus 로고
    • Synthesis and structure of stereoisomeric multivicinal hexafluoroalkanes
    • Hunter L, Kirsch P, Slawin AMZ, O’Hagan D (2009) Synthesis and structure of stereoisomeric multivicinal hexafluoroalkanes. Angew Chem Int Ed 48:5457–5460
    • (2009) Angew Chem Int Ed , vol.48 , pp. 5457-5460
    • Hunter, L.1    Kirsch, P.2    Slawin, A.3    O’Hagan, D.4
  • 29
    • 0037207628 scopus 로고    scopus 로고
    • The c-f bond as a tool in the conformational control of amides
    • Briggs CRS, O’Hagan D, Howard JAK, Yulfi DS (2003) The C-F bond as a tool in the conformational control of amides. J Fluor Chem 119:9–13
    • (2003) J Fluor Chem , vol.119 , pp. 9-13
    • Briggs, C.1    O’Hagan, D.2    Howard, J.3    Yulfi, D.S.4
  • 30
    • 84856382414 scopus 로고    scopus 로고
    • Intermolecular and intramolecular hydrogen bonds involving fluorine atoms: Implications for recognition, selectivity, and chemical properties
    • Dalvit D, Vulpetti A (2012) Intermolecular and intramolecular hydrogen bonds involving fluorine atoms: implications for recognition, selectivity, and chemical properties. ChemMedChem 7:262–272
    • (2012) Chemmedchem , vol.7 , pp. 262-272
    • Dalvit, D.1    Vulpetti, A.2
  • 31
    • 25144510381 scopus 로고    scopus 로고
    • The vicinal f-c-c-f moiety as a tool for influencing peptide conformation
    • Schϋler M, O’Hagan D, Slawin AMZ (2005) The vicinal F-C-C-F moiety as a tool for influencing peptide conformation. Chem Commun 4324–4326
    • (2005) Chem Commun , pp. 4324-4326
    • Schϋler, M.1    O’Hagan, D.2    Slawin, A.3
  • 32
    • 33750973914 scopus 로고    scopus 로고
    • The vicinal difluoro motif: The synthesis and conformation of erythro - and threo -diastereomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives
    • O’Hagan D, Rzepa HS, Schϋler M, Slawin AMZ (2006) The vicinal difluoro motif: the synthesis and conformation of erythro - and threo -diastereomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives. Beilstein J Org Chem. doi: 10.1186/1860-5397-2-19
    • (2006) Beilstein J Org Chem
    • O’Hagan, D.1    Rzepa, H.S.2    Schϋler, M.3    Slawin, A.4
  • 33
    • 65549108711 scopus 로고    scopus 로고
    • Synthesis and vanilloid receptor (Trpv1) activity of the enantiomers of α-fluorinated capsaicin
    • Winkler M, Moraux T, Khairy HA, Scott RH, Slawin AMZ, O’Hagan D (2009) Synthesis and vanilloid receptor (TRPV1) activity of the enantiomers of α-fluorinated capsaicin. ChemBioChem 10:823–828
    • (2009) Chembiochem , vol.10 , pp. 823-828
    • Winkler, M.1    Moraux, T.2    Khairy, H.A.3    Scott, R.H.4    Slawin, A.5    O’Hagan, D.6
  • 35
    • 0034175168 scopus 로고    scopus 로고
    • The preferred conformation of n-β-fluoroethylamides: Observation of the fluorine amide gauche effect
    • O’Hagan D, Bilton C, Howard JAK, Knight L, Tozer DJ (2001) The preferred conformation of N-β-fluoroethylamides: observation of the fluorine amide gauche effect. J Chem Soc Perkin Trans 2:605–607
    • (2001) J Chem Soc Perkin Trans , vol.2 , pp. 605-607
    • O’Hagan, D.1    Bilton, C.2    Howard, J.3    Knight, L.4    Tozer, D.J.5
  • 36
    • 1842663065 scopus 로고    scopus 로고
    • Some influences of fluorine in bioorganic chemistry
    • O’Hagan D, Rzepa HS (1997) Some influences of fluorine in bioorganic chemistry. Chem Commun 645–652
    • (1997) Chem Commun , pp. 645-652
    • O’Hagan, D.1    Rzepa, H.S.2
  • 39
    • 0041708049 scopus 로고    scopus 로고
    • Stereoelectronic effects on collagen stability: The dichotomy of 4-fluoroproline diastereomers
    • Hodges JA, Raines RT (2003) Stereoelectronic effects on collagen stability: the dichotomy of 4-fluoroproline diastereomers. J Am Chem Soc 125:9262–9263
    • (2003) J am Chem Soc , vol.125 , pp. 9262-9263
    • Hodges, J.A.1    Raines, R.T.2
  • 40
    • 0043023397 scopus 로고    scopus 로고
    • Characterization of collagen model peptides containing 4-fluoroproline: (4(s)-fluoroproline-pro-gly)10 forms a triple helix, but (4(r)-fluoroproline-pro-gly)10 does not
    • Doi M, Nishi Y, Uchiyama S, Nisiuchi Y, Nakazawa T, Ohkubo T, Kobayasji Y (2003) Characterization of collagen model peptides containing 4-fluoroproline: (4(S)-fluoroproline-Pro-Gly)10 forms a triple helix, but (4(R)-fluoroproline-Pro-Gly)10 does not. J Am Chem Soc 125:9922–9923
    • (2003) J am Chem Soc , vol.125 , pp. 9922-9923
    • Doi, M.1    Nishi, Y.2    Uchiyama, S.3    Nisiuchi, Y.4    Nakazawa, T.5    Ohkubo, T.6    Kobayasji, Y.7
  • 41
    • 27844565701 scopus 로고    scopus 로고
    • Stereoelectronic and steric effects in the collagen triple helix: Toward a code for strand association
    • Hodges JA, Raines RT (2005) Stereoelectronic and steric effects in the collagen triple helix: toward a code for strand association. J Am Chem Soc 127:15923–15932
    • (2005) J am Chem Soc , vol.127 , pp. 15923-15932
    • Hodges, J.A.1    Raines, R.T.2
  • 42
    • 67649647838 scopus 로고    scopus 로고
    • Origin of the stability conferred upon collagen by fluorination
    • Shoulders MD, Kamer KJ, Raines RT (2009) Origin of the stability conferred upon collagen by fluorination. Bioorg Med Chem Lett 19:3859–3862
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 3859-3862
    • Shoulders, M.D.1    Kamer, K.J.2    Raines, R.T.3
  • 44
    • 0037139532 scopus 로고    scopus 로고
    • Collagen stability: Insights from nmr spectroscopic and hybrid density functional computational investigations of the effect of electronegative substituents on prolylring conformations
    • DeRider ML, Wilkins SJ, Waddell MJ, Bretscher LE, Weinhold F, Raines RT, Markley JL (2002) Collagen stability: insights from NMR spectroscopic and hybrid density functional computational investigations of the effect of electronegative substituents on prolylring conformations. J Am Chem Soc 124:2497–2505
    • (2002) J am Chem Soc , vol.124 , pp. 2497-2505
    • DeRider, M.L.1    Wilkins, S.J.2    Waddell, M.J.3    Bretscher, L.E.4    Weinhold, F.5    Raines, R.T.6    Markley, J.L.7
  • 45
    • 27844585568 scopus 로고    scopus 로고
    • A new set of molecular mechanics parameters for hydroxyproline and its use in molecular dynamics simulations of collagen-like peptides
    • Park S, Radmer RJ, Klein TE, Pande VS (2005) A new set of molecular mechanics parameters for hydroxyproline and its use in molecular dynamics simulations of collagen-like peptides. J Comput Chem 26:1612–1616
    • (2005) J Comput Chem , vol.26 , pp. 1612-1616
    • Park, S.1    Radmer, R.J.2    Klein, T.E.3    Pande, V.S.4
  • 46
    • 33750361975 scopus 로고    scopus 로고
    • Energetics of an n → π* interaction that impacts protein structure
    • Hodges JA, Raines RT (2006) Energetics of an n → π* interaction that impacts protein structure. Org Lett 8:4695–4697
    • (2006) Org Lett , vol.8 , pp. 4695-4697
    • Hodges, J.A.1    Raines, R.T.2
  • 47
    • 0038245117 scopus 로고    scopus 로고
    • An electronic effect on protein structure
    • Hinderaker MP, Raines RT (2003) An electronic effect on protein structure. Protein Sci 12:1188–1194
    • (2003) Protein Sci , vol.12 , pp. 1188-1194
    • Hinderaker, M.P.1    Raines, R.T.2
  • 48
    • 33646127611 scopus 로고    scopus 로고
    • 2005 emil thomas kaiser award
    • Raines RT (2006) 2005 Emil Thomas Kaiser Award. Protein Sci 15:1219–1225
    • (2006) Protein Sci , vol.15 , pp. 1219-1225
    • Raines, R.T.1
  • 49
    • 84962360895 scopus 로고    scopus 로고
    • Understanding the role of stereoelectronic effects in determining collagen stability: A quantum mechanical/molecular mechanical study of (proline-proline-glycine) n polypeptides
    • Improta R, Mele F, Crescenzi O, Benzi C, Barone V (2002) Understanding the role of stereoelectronic effects in determining collagen stability: a quantum mechanical/molecular mechanical study of (proline-proline-glycine) n polypeptides. J Am Chem Soc 124:7857–7865
    • (2002) J am Chem Soc , vol.124 , pp. 7857-7865
    • Improta, R.1    Mele, F.2    Crescenzi, O.3    Benzi, C.4    Barone, V.5
  • 50
    • 33845789244 scopus 로고    scopus 로고
    • Fluoroproline flip-flop: Regiochemical reversal of a stereoelectronic effect on peptide and protein structures
    • Kim W, Hardcastle KL, Conticello VP (2006) Fluoroproline flip-flop: regiochemical reversal of a stereoelectronic effect on peptide and protein structures. Angew Chem Int Ed 45:8141–8814
    • (2006) Angew Chem Int Ed , vol.45 , pp. 8141-8814
    • Kim, W.1    Hardcastle, K.L.2    Conticello, V.P.3
  • 51
    • 40649115176 scopus 로고    scopus 로고
    • Incorporation of fluoroprolines to proctolin: Study on the effect of a fluorine atom towards peptidic conformation
    • Kitamoto T, Ozawa T, Abe M, Marubayashi S, Yamazaki T (2008) Incorporation of fluoroprolines to proctolin: study on the effect of a fluorine atom towards peptidic conformation. J Fluor Chem 129:286–293
    • (2008) J Fluor Chem , vol.129 , pp. 286-293
    • Kitamoto, T.1    Ozawa, T.2    Abe, M.3    Marubayashi, S.4    Yamazaki, T.5
  • 52
    • 1642345348 scopus 로고    scopus 로고
    • The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated
    • Briggs CRS, Allen MJ, O’Hagan D, Tozer DJ, Slawin AMZ, Goeta AE, Howard JAK (2004) The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated. Org Biomol Chem 2:732–740
    • (2004) Org Biomol Chem , vol.2 , pp. 732-740
    • Briggs, C.1    Allen, M.J.2    O’Hagan, D.3    Tozer, D.J.4    Slawin, A.5    Goeta, A.E.6    Howard, J.7
  • 53
    • 0001267759 scopus 로고
    • Protonated 3- fluoropiperidines: An unusual fluoro directing effect and a test for quantitative theories of solvation
    • Lankin DC, Chandrakumar NS, Rao SN, Spangler DP, Snyder JP (1993) Protonated 3- fluoropiperidines: an unusual fluoro directing effect and a test for quantitative theories of solvation. J Am Chem Soc 115:3356–3357
    • (1993) J am Chem Soc , vol.115 , pp. 3356-3357
    • Lankin, D.C.1    Chandrakumar, N.S.2    Rao, S.N.3    Spangler, D.P.4    Snyder, J.P.5
  • 54
    • 0034716326 scopus 로고    scopus 로고
    • The unexpected diaxial orientation of cis-3, 5-difluoropiperidine in water: A potent cf – nh charge-dipole effect
    • Snyder JP, Chandrakumar NS, Sato H, Lankin DC (2000) The unexpected diaxial orientation of cis-3, 5-difluoropiperidine in water: a potent CF – NH charge-dipole effect. J Am Chem Soc 122:544–545
    • (2000) J am Chem Soc , vol.122 , pp. 544-545
    • Snyder, J.P.1    Chandrakumar, N.S.2    Sato, H.3    Lankin, D.C.4
  • 55
    • 84962377223 scopus 로고    scopus 로고
    • Snyder jp (2005) 3-fluoropiperidines and n-methyl-3-fluoropiperidinium salts: The persistence of axial fluorine
    • Sun A, Lankin DC, Hardcastle K, Snyder JP (2005) 3-Fluoropiperidines and N-methyl-3-fluoropiperidinium salts: the persistence of axial fluorine. Chem Eur J 11:1579–1591
    • Chem Eur J , vol.11 , pp. 1579-1591
    • Sun, A.1    Lankin, D.C.2    Hardcastle, K.3
  • 56
    • 0015932846 scopus 로고
    • Conformation of cis - and trans -4-fluoro-l-proline in aqueous solution
    • Gerig JT, McLeod RS (1973) Conformation of cis - and trans -4-fluoro-L-proline in aqueous solution. J Am Chem Soc 95:5725–5729
    • (1973) J am Chem Soc , vol.95 , pp. 5725-5729
    • Gerig, J.T.1    McLeod, R.S.2
  • 58
    • 36849013490 scopus 로고    scopus 로고
    • Enantiomers of 4-amino- 3-fluorobutanoic acid as substrates for γ-aminobutyric acid aminotransferase: Conformational probes for gaba binding
    • Clift MD, Ji H, Deniau GP, O’Hagan D, Silverman RB (2007) Enantiomers of 4-amino- 3-fluorobutanoic acid as substrates for γ-aminobutyric acid aminotransferase: conformational probes for GABA binding. Biochemistry 46:13819–13828
    • (2007) Biochemistry , vol.46 , pp. 13819-13828
    • Clift, M.D.1    Ji, H.2    Deniau, G.P.3    O’Hagan, D.4    Silverman, R.B.5
  • 59
    • 79959878607 scopus 로고    scopus 로고
    • Agonist responses of (r)- and (s)-3-fluoro-γ-aminobutyric acids suggest an enantiomeric fold for gaba binding to gabac receptors
    • Yamamoto I, Deniau GP, Gavande N, Chebib M, Johnston GAR, O’Hagan D (2011) Agonist responses of (r)- and (s)-3-fluoro-γ-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABAC receptors. Chem Commun 47:7956–7958
    • (2011) Chem Commun , vol.47 , pp. 7956-7958
    • Yamamoto, I.1    Deniau, G.P.2    Gavande, N.3    Chebib, M.4    Johnston, G.5    O’Hagan, D.6
  • 60
    • 84863460309 scopus 로고    scopus 로고
    • O’hagan d (2012) 3-Fluoro-N-methyl-D-asaprtic acid (3f-nmda) stereoisomers as conformational probes for exploring agonist binding at nmda receptors
    • Chia PW, Livesey MR, Slawin AMZ, van Mourik T, Wyllie DJA, O’Hagan D (2012) 3-Fluoro-N-methyl-D-asaprtic acid (3F-NMDA) stereoisomers as conformational probes for exploring agonist binding at NMDA receptors. Chem Eur J 18:8813–8819
    • Chem Eur J , vol.18 , pp. 8813-8819
    • Chia, P.W.1    Livesey, M.R.2    Slawin, A.3    Van Mourik, T.4    Wyllie, D.5
  • 62
    • 79951657834 scopus 로고    scopus 로고
    • Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidine attached to acridine ligands affects their interactions with g-quadruplex dna
    • Campbell NH, Smith DL, Reszka AP, Neidle S, O’hagan D (2011) Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidine attached to acridine ligands affects their interactions with G-quadruplex DNA. Org Biomol Chem 9:1328–1331
    • (2011) Org Biomol Chem , vol.9 , pp. 1328-1331
    • Campbell, N.H.1    Smith, D.L.2    Reszka, A.P.3    Neidle, S.4    O’hagan, D.5
  • 63
    • 37049082687 scopus 로고
    • Conformational analysis. Part an nmr and theoretical investigation of the gauche effect in fluoroethanols
    • Abraham RJ, Chambers EJ, Thomas AW (1994) Conformational analysis. Part An NMR and theoretical investigation of the gauche effect in fluoroethanols. J Chem Soc Perkin Trans 2:949–955
    • (1994) J Chem Soc Perkin Trans , vol.2 , pp. 949-955
    • Abraham, R.J.1    Chambers, E.J.2    Thomas, A.W.3
  • 64
    • 0001253411 scopus 로고    scopus 로고
    • Conformational analysis. Part oh-f hydrogen bonding and the conformation of trans-2-fluorocyclohexanol
    • Abraham RJ, Smith TAD, Thomas AW (1996) Conformational analysis. Part OH-F hydrogen bonding and the conformation of trans-2-fluorocyclohexanol. J Chem Soc Perkin Trans 2:1949–1955
    • (1996) J Chem Soc Perkin Trans , vol.2 , pp. 1949-1955
    • Abraham, R.J.1    Smith, T.2    Thomas, A.W.3
  • 65
    • 0001365893 scopus 로고
    • 9α-fluoro derivatives of cortisone and hydrocortisone
    • Fried J, Sabo EF (1954) 9α-Fluoro derivatives of cortisone and hydrocortisone. J Am Chem Soc 76:1455–1456
    • (1954) J am Chem Soc , vol.76 , pp. 1455-1456
    • Fried, J.1    Sabo, E.F.2
  • 66
    • 78651057618 scopus 로고
    • Biological effects of 9 α-fluorohydrocortisone and related halogenated steroids in animals
    • Fried J (1955) Biological effects of 9 α-fluorohydrocortisone and related halogenated steroids in animals. Ann N Y Acad Sci 61:573–581
    • (1955) Ann N Y Acad Sci , vol.61 , pp. 573-581
    • Fried, J.1
  • 67
    • 77958039726 scopus 로고    scopus 로고
    • Fluorine in health care: Organofluorine-containing blockbuster drugs
    • O’Hagan D (2010) Fluorine in health care: organofluorine-containing blockbuster drugs. J Fluor Chem 131:1071–1081
    • (2010) J Fluor Chem , vol.131 , pp. 1071-1081
    • O’Hagan, D.1
  • 68
    • 0025030179 scopus 로고
    • Concerning the relative acidities of simple alcohols
    • Mock W, Zhang JZ (1990) Concerning the relative acidities of simple alcohols. Tetrahedron Lett 31:5687–5688
    • (1990) Tetrahedron Lett , vol.31 , pp. 5687-5688
    • Mock, W.1    Zhang, J.Z.2
  • 69
    • 0015912235 scopus 로고
    • A comparison of the structure of six corticosteroids
    • Weeks CM, Duax WL, Wolff ME (1973) A comparison of the structure of six corticosteroids. J Am Chem Soc 95:2865–2868
    • (1973) J am Chem Soc , vol.95 , pp. 2865-2868
    • Weeks, C.M.1    Duax, W.L.2    Wolff, M.E.3
  • 71
    • 0034826462 scopus 로고    scopus 로고
    • Asymmetric synthesis of chiral organofluorine compounds: Use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of hiv protease inhibitors
    • Myers AG, Barbay JK, Zhong B (2001) Asymmetric synthesis of chiral organofluorine compounds: use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of HIV protease inhibitors. J Am Chem Soc 123:7207–7219
    • (2001) J am Chem Soc , vol.123 , pp. 7207-7219
    • Myers, A.G.1    Barbay, J.K.2    Zhong, B.3
  • 72
    • 17244371011 scopus 로고    scopus 로고
    • α-fluorinated ethers, thioethers, and amines: Anomerically biased species
    • Leroux F, Jeschke P, Schlosser M (2005) α-Fluorinated ethers, thioethers, and amines: anomerically biased species. Chem Rev 105:827–856
    • (2005) Chem Rev , vol.105 , pp. 827-856
    • Leroux, F.1    Jeschke, P.2    Schlosser, M.3
  • 73
    • 0035833027 scopus 로고    scopus 로고
    • Novel heteroaryl replacements of aromatic 3-tetrafluoroethoxy substituents in trifluoro-3-(Tertiaryamino)-2-propanols as potent inhibitors of cholesterol ester transfer protein
    • Massa MA, Spangler DP, Durley RC, Hickory BS, Connolly DT, Witherbee BJ, Smith ME, Sikorski JA (2001) Novel heteroaryl replacements of aromatic 3-tetrafluoroethoxy substituents in trifluoro-3-(tertiaryamino)-2-propanols as potent inhibitors of cholesterol ester transfer protein. Bioorg Med Chem Lett 11:1625–1628
    • (2001) Bioorg Med Chem Lett , vol.11 , pp. 1625-1628
    • Massa, M.A.1    Spangler, D.P.2    Durley, R.C.3    Hickory, B.S.4    Connolly, D.T.5    Witherbee, B.J.6    Smith, M.E.7    Sikorski, J.A.8
  • 75
    • 33947089034 scopus 로고
    • Molecular orbital theory of the electronic structure of organic compounds. Xii. Conformations, stabilities, and charge distributions in monosubstituted benzenes
    • Hehre WJ, Radom L, Pople JA (1972) Molecular orbital theory of the electronic structure of organic compounds. XII. Conformations, stabilities, and charge distributions in monosubstituted benzenes. J Am Chem Soc 94:1496–1504
    • (1972) J am Chem Soc , vol.94 , pp. 1496-1504
    • Hehre, W.J.1    Radom, L.2    Pople, J.A.3
  • 76
    • 0018456201 scopus 로고
    • Methoxy group nonplanarity in o -dimethoxybenzenes. Simple predictive models for conformations and rotational barriers in alkoxyaromatics
    • Anderson GM III, Kollman PA, Domelsmith LN, Houk KN (1979) Methoxy group nonplanarity in o -dimethoxybenzenes. Simple predictive models for conformations and rotational barriers in alkoxyaromatics. J Am Chem Soc 101:2344–2352
    • (1979) J am Chem Soc , vol.101 , pp. 2344-2352
    • Anderson, G.M.1    Kollman, P.A.2    Domelsmith, L.N.3    Houk, K.N.4
  • 77
    • 0001070727 scopus 로고
    • Conformational fl exibility of the methoxyphenyl group studies by statistical analysis of crystal structure data
    • Hummel W, Huml K, Bürgi H-B (1988) Conformational fl exibility of the methoxyphenyl group studies by statistical analysis of crystal structure data. Helv Chim Acta 71:1291–1302
    • (1988) Helv Chim Acta , vol.71 , pp. 1291-1302
    • Hummel, W.1    Huml, K.2    Bürgi, H.-B.3
  • 78
    • 39449105474 scopus 로고    scopus 로고
    • Small molecule conformational preferences derived from crystal structure data. A medicinal chemistry focused analysis
    • Brameld KA, Kuhn B, Reuter DC, Stahl M (2008) Small molecule conformational preferences derived from crystal structure data. A medicinal chemistry focused analysis. J Chem Inf Model 48:1–24
    • (2008) J Chem Inf Model , vol.48 , pp. 1-24
    • Brameld, K.A.1    Kuhn, B.2    Reuter, D.C.3    Stahl, M.4
  • 79
    • 33748542524 scopus 로고
    • Allylic strain in six-membered rings
    • Johnson F (1968) Allylic strain in six-membered rings. Chem Rev 68:375–413
    • (1968) Chem Rev , vol.68 , pp. 375-413
    • Johnson, F.1
  • 80
    • 0037427752 scopus 로고    scopus 로고
    • On the structure and torsional potential of trifluoromethoxybenzene: An ab initio and density functional study
    • Klocker J, Karpfen A, Wolschann P (2003) On the structure and torsional potential of trifluoromethoxybenzene: an ab initio and density functional study. Chem Phys Lett 367:566–575
    • (2003) Chem Phys Lett , vol.367 , pp. 566-575
    • Klocker, J.1    Karpfen, A.2    Wolschann, P.3
  • 81
    • 84862646886 scopus 로고    scopus 로고
    • An unexpected and signifi cantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols
    • Graton J, Wang Z, Brossard A-M, Monteiro DG, Questel J-YL, Linclau B (2012) An unexpected and signifi cantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. Angew Chem Int Ed 51:6176–6180
    • (2012) Angew Chem Int Ed , vol.51 , pp. 6176-6180
    • Graton, J.1    Wang, Z.2    Brossard, A.-M.3    Monteiro, D.G.4    Questel, J.-Y.5    Linclau, B.6
  • 82
    • 80052974259 scopus 로고    scopus 로고
    • Improving drug candidates by design: A focus on physicochemical properties as a means of improving compound disposition and safety
    • Meanwell N (2011) Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem Res Toxicol 24:1420–1456
    • (2011) Chem Res Toxicol , vol.24 , pp. 1420-1456
    • Meanwell, N.1
  • 83
    • 65549132575 scopus 로고    scopus 로고
    • Pharmacological promiscuity: Dependence on compound properties and target specificity in a set of recent roche compounds
    • Peters JE, Schnider P, Mattei P, Kansy M (2009) Pharmacological promiscuity: dependence on compound properties and target specificity in a set of recent Roche compounds. ChemMedChem 4:680–686
    • (2009) Chemmedchem , vol.4 , pp. 680-686
    • Peters, J.E.1    Schnider, P.2    Mattei, P.3    Kansy, M.4
  • 85
    • 33747505446 scopus 로고    scopus 로고
    • Medicinal chemistry of herg optimizations: Highlights and hang-ups
    • Jamieson C, Moir EM, Rankovic Z, Wishart G (2006) Medicinal chemistry of hERG optimizations: highlights and hang-ups. J Med Chem 49:5029–5046
    • (2006) J Med Chem , vol.49 , pp. 5029-5046
    • Jamieson, C.1    Moir, E.M.2    Rankovic, Z.3    Wishart, G.4
  • 86
    • 0034353951 scopus 로고    scopus 로고
    • Cafca: A novel tool for the calculation of amphiphilic properties of charged drug molecules
    • Fischer H, Kansy M, Bur D (2000) CAFCA: a novel tool for the calculation of amphiphilic properties of charged drug molecules. Chimia 54:640–645
    • (2000) Chimia , vol.54 , pp. 640-645
    • Fischer, H.1    Kansy, M.2    Bur, D.3
  • 87
    • 0011786864 scopus 로고
    • Prediction of the strengths of organic bases
    • Clark J, Perrin DD (1964) Prediction of the strengths of organic bases. Q Rev Chem Soc 18:295–320
    • (1964) Q Rev Chem Soc , vol.18 , pp. 295-320
    • Clark, J.1    Perrin, D.D.2
  • 89
    • 0038582053 scopus 로고
    • Relative reactivity of amines and oxyanions toward proton abstraction from nitroethane. Electrostatic effects and the reactivity-selectivity principle
    • Bruice PY (1984) Relative reactivity of amines and oxyanions toward proton abstraction from nitroethane. Electrostatic effects and the reactivity-selectivity principle. J Am Chem Soc 106:5959–5964
    • (1984) J am Chem Soc , vol.106 , pp. 5959-5964
    • Bruice, P.Y.1
  • 90
    • 0000485791 scopus 로고
    • Acidities and partition coefficients of fluoromethanesulfonamides
    • Trepka RD, Harrington JK, Belisle JW (1974) Acidities and partition coefficients of fluoromethanesulfonamides. J Org Chem 39:1094–1098
    • (1974) J Org Chem , vol.39 , pp. 1094-1098
    • Trepka, R.D.1    Harrington, J.K.2    Belisle, J.W.3
  • 92
    • 4243664295 scopus 로고
    • A survey of hammett substituent constants and resonance field parameters
    • Hansch C, Leo A, Taft RW (1991) A survey of Hammett substituent constants and resonance field parameters. Chem Rev 91:165c–195c
    • (1991) Chem Rev , vol.91 , pp. 165c-195c
    • Hansch, C.1    Leo, A.2    Taft, R.W.3
  • 94
    • 0032546913 scopus 로고    scopus 로고
    • Parametrization of substituents: Effects of fluorine and other heteroatoms on oh, nh, and ch acidities
    • Schlosser M (1998) Parametrization of substituents: effects of fluorine and other heteroatoms on OH, NH, and CH acidities. Angew Chem Int Ed 110:1496–1513
    • (1998) Angew Chem Int Ed , vol.110 , pp. 1496-1513
    • Schlosser, M.1
  • 95
    • 2542432021 scopus 로고    scopus 로고
    • 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
    • Olsen J, Seiler P, Wagner B, Fischer H, Tschopp T, Obst-Sander U, Banner DW, Kansy M, Muller K, Diederich F (2004) 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. Org Biomol Chem 2:1339–1352
    • (2004) Org Biomol Chem , vol.2 , pp. 1339-1352
    • Olsen, J.1    Seiler, P.2    Wagner, B.3    Fischer, H.4    Tschopp, T.5    Obst-Sander, U.6    Banner, D.W.7    Kansy, M.8    Muller, K.9    Diederich, F.10
  • 97
    • 80655146733 scopus 로고    scopus 로고
    • Synthesis, molecular modeling studies and biological evaluation of fluorine substituted analogs of gw 501516
    • Ciocoiu CC, Ravna AW, Sylte I, Rustan AC, Hansen TV (2011) Synthesis, molecular modeling studies and biological evaluation of fluorine substituted analogs of GW 501516. Bio org Med Chem 19:6982–6988
    • (2011) Bio Org Med Chem , vol.19 , pp. 6982-6988
    • Ciocoiu, C.C.1    Ravna, A.W.2    Sylte, I.3    Rustan, A.C.4    Hansen, T.V.5
  • 98
    • 79952804851 scopus 로고    scopus 로고
    • Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry
    • Ishikawa M, Hashimoto Y (2011) Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry. J Med Chem 54:1539–1554
    • (2011) J Med Chem , vol.54 , pp. 1539-1554
    • Ishikawa, M.1    Hashimoto, Y.2
  • 103
    • 34548540174 scopus 로고    scopus 로고
    • The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine
    • Welch JT, Lim DS (2007) The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine. Bioorg Med Chem 15:6659–6666
    • (2007) Bioorg Med Chem , vol.15 , pp. 6659-6666
    • Welch, J.T.1    Lim, D.S.2
  • 104
    • 84867404690 scopus 로고    scopus 로고
    • Synthetic chemistry and biological activity of pentafluorosulphanyl (Sf5) organic molecules
    • Altomonte S, Zanda M (2012) Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules. J Fluor Chem 143:57–93
    • (2012) J Fluor Chem , vol.143 , pp. 57-93
    • Altomonte, S.1    Zanda, M.2
  • 107
    • 0021318222 scopus 로고
    • The synthesis and biology of fluorinated prostacyclins
    • Barnette WE (1984) The synthesis and biology of fluorinated prostacyclins. CRC Crit Rev Biochem 15:201–235
    • (1984) CRC Crit Rev Biochem , vol.15 , pp. 201-235
    • Barnette, W.E.1
  • 108
    • 0030848734 scopus 로고    scopus 로고
    • In vivo metabolism-based discovery of a potent cholesterol absorption inhibitor, sch58235, in the rat and rhesus monkey through the identification of the active metabolites of sch48461
    • Heek M, France CF, Compton DS, McLeod RL, Yumibe NP, Alton KB, Sybertz EJ, Davies HR Jr (1997) In vivo metabolism-based discovery of a potent cholesterol absorption inhibitor, SCH58235, in the rat and rhesus monkey through the identification of the active metabolites of SCH48461. J Pharmacol Exp Ther 283:157–163
    • (1997) J Pharmacol Exp Ther , vol.283 , pp. 157-163
    • Heek, M.1    France, C.F.2    Compton, D.S.3    McLeod, R.L.4    Yumibe, N.P.5    Alton, K.B.6    Sybertz, E.J.7    Davies, H.R.8
  • 109
    • 0346731237 scopus 로고    scopus 로고
    • The discovery of ezetimibe: A view from outside the receptor
    • Clader JW (2004) The discovery of ezetimibe: a view from outside the receptor. J Med Chem 47:1–9
    • (2004) J Med Chem , vol.47 , pp. 1-9
    • Clader, J.W.1
  • 111
    • 0032510318 scopus 로고    scopus 로고
    • Discovery of 1-(4-fluorophenyl)-(3r)-[3-(4-fluorophenyl)-(3s)-hydroxypropyl]-(4s)-(4-hydroxyphenyl)-2-azetidinone (sch 58235): A designed, potent, orally active inhibitor of cholesterol absorption
    • Rosenblum SB, Huynh T, Afonso A, Davis HR Jr, Yumibe N, Clader JW, Burnett DA (1998) Discovery of 1-(4-fluorophenyl)-(3r)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4s)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): a designed, potent, orally active inhibitor of cholesterol absorption. J Med Chem 41:973–980
    • (1998) J Med Chem , vol.41 , pp. 973-980
    • Rosenblum, S.B.1    Huynh, T.2    Afonso, A.3    Davis, H.R.4    Yumibe, N.5    Clader, J.W.6    Burnett, D.A.7
  • 112
    • 84863856481 scopus 로고    scopus 로고
    • Mitigating heterocycle metabolism in drug discovery
    • St Jean Jr DJ, Fotsch C (2012) Mitigating heterocycle metabolism in drug discovery. J Med Chem 55:6002–6020
    • (2012) J Med Chem , vol.55 , pp. 6002-6020
    • St Jean, D.J.1    Fotsch, C.2
  • 117
    • 0031777752 scopus 로고    scopus 로고
    • Occurrence of the nih shift upon the cytochrome p450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes
    • Koerts J, Soffers AE, Vervoort J, De Jager A, Rietjens IM (1998) Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes. Chem Res Toxicol 11:503–512
    • (1998) Chem Res Toxicol , vol.11 , pp. 503-512
    • Koerts, J.1    Soffers, A.E.2    Vervoort, J.3    De Jager, A.4    Rietjens, I.M.5
  • 118
    • 0034055226 scopus 로고    scopus 로고
    • Urinary metabolites of a novel quinoxaline non-nucleoside reverse transcriptase inhibitor in rabbit, mouse and human: Identification of fluorine nih shift metabolites using nmr and tandem ms
    • Dear GJ, Ismail IM, Mutch PJ, Plumb RS, Davies LS (2000) Urinary metabolites of a novel quinoxaline non-nucleoside reverse transcriptase inhibitor in rabbit, mouse and human: identification of fluorine NIH shift metabolites using NMR and tandem MS. Xenobiotica 30:407–426
    • (2000) Xenobiotica , vol.30 , pp. 407-426
    • Dear, G.J.1    Ismail, I.M.2    Mutch, P.J.3    Plumb, R.S.4    Davies, L.S.5
  • 119
    • 0028203902 scopus 로고
    • Effect of monolayer surface pressure on the activities of phosphoinositide-specifi c phospholipase c-β.1, -γ.1, and δ1
    • Boguslavsky V, Bebecchi M, Morris AJ, Jhon DY, Rhee SG, McLaughlin S (1994) Effect of monolayer surface pressure on the activities of phosphoinositide-specifi c phospholipase C-β.1, -γ.1, and δ1. Biochemistry 33:3032–3037
    • (1994) Biochemistry , vol.33 , pp. 3032-3037
    • Boguslavsky, V.1    Bebecchi, M.2    Morris, A.J.3    Jhon, D.Y.4    Rhee, S.G.5    McLaughlin, S.6
  • 120
    • 0029760018 scopus 로고    scopus 로고
    • Binding of hisactophilin i and ii to lipid membranes is controlled by a ph-dependent myristoyl−histidine switch
    • Hanakam F, Gerisch G, Lotz S, Alt T, Seelig A (1996) Binding of hisactophilin I and II to lipid membranes is controlled by a pH-dependent myristoyl−histidine switch. Biochemistry 35:11036–11044
    • (1996) Biochemistry , vol.35 , pp. 11036-11044
    • Hanakam, F.1    Gerisch, G.2    Lotz, S.3    Alt, T.4    Seelig, A.5
  • 121
    • 0031695039 scopus 로고    scopus 로고
    • Blood-brain barrier permeation: Molecular parameters governing passive diffusion
    • Fischer H, Gottschlich R, Seelig A (1998) Blood-brain barrier permeation: molecular parameters governing passive diffusion. J Membr Biol 165:201–211
    • (1998) J Membr Biol , vol.165 , pp. 201-211
    • Fischer, H.1    Gottschlich, R.2    Seelig, A.3
  • 122
    • 14744272833 scopus 로고    scopus 로고
    • The use of biopharmaceutical classification of drugs in drug discover and development: Current status and future extensions
    • Lennarnas H, Abrahamsson B (2005) The use of biopharmaceutical classification of drugs in drug discover and development: current status and future extensions. J Pharm Pharmacol 57:273–285
    • (2005) J Pharm Pharmacol , vol.57 , pp. 273-285
    • Lennarnas, H.1    Abrahamsson, B.2
  • 123
    • 0034926661 scopus 로고    scopus 로고
    • Fluorine substituent effects (On bioactivity)
    • Smart B (2001) Fluorine substituent effects (on bioactivity). J Fluor Chem 109:3–11
    • (2001) J Fluor Chem , vol.109 , pp. 3-11
    • Smart, B.1
  • 124
    • 0028240136 scopus 로고
    • Synthesis, structure-activity relationships, and pharmacological evaluation of a series of fluorinated 3-benzyl-5-indolecarboxamides: Identification of 4-[[5-[((2r)-2-methyl- 4,4,4-trifluorobutyl)carbamoyl]-1-methylindol-3-yl]methyl]-3methoxy-n-[(2-methylphenyl)sulfonyl]benzamide, a potent, orally active antagonist of leukotrienes d4 and e4
    • Jacobs RT, Bernstein PR, Cronk LA, Vacek EP, Newcomb LF, Aharony D, Buckner CK, Kusner EJ (1994) Synthesis, structure-activity relationships, and pharmacological evaluation of a series of fluorinated 3-benzyl-5-indolecarboxamides: identification of 4-[[5-[((2R)-2-methyl- 4,4,4-trifluorobutyl)carbamoyl]-1-methylindol-3-yl]methyl]-3methoxy-N-[(2-methylphenyl)sulfonyl]benzamide, a potent, orally active antagonist of leukotrienes D4 and E4. J Med Chem 37:1282–1297
    • (1994) J Med Chem , vol.37 , pp. 1282-1297
    • Jacobs, R.T.1    Bernstein, P.R.2    Cronk, L.A.3    Vacek, E.P.4    Newcomb, L.F.5    Aharony, D.6    Buckner, C.K.7    Kusner, E.J.8
  • 129
    • 4744373354 scopus 로고    scopus 로고
    • Hydrogen-bonding interactions of covalently bonded fluorine atoms: From crystallographic data to a new angular function in the grid force field
    • Carosati E, Sciabola S, Cruciani G (2004) Hydrogen-bonding interactions of covalently bonded fluorine atoms: from crystallographic data to a new angular function in the GRID force field. J Med Chem 47:5114–5125
    • (2004) J Med Chem , vol.47 , pp. 5114-5125
    • Carosati, E.1    Sciabola, S.2    Cruciani, G.3
  • 130
    • 0034270743 scopus 로고    scopus 로고
    • The structure of liquid and supercritical deuterium fluoride from neutron scattering and using high-pressure techniques
    • Pfleiderer T, Waldner I, Bertagnolli H, Tödheide K, Fischer HE (2000) The structure of liquid and supercritical deuterium fluoride from neutron scattering and using high-pressure techniques. J Chem Phys 113:3690–3696
    • (2000) J Chem Phys , vol.113 , pp. 3690-3696
    • Pfleiderer, T.1    Waldner, I.2    Bertagnolli, H.3    Tödheide, K.4    Fischer, H.E.5
  • 132
    • 0004524514 scopus 로고
    • Intermolecular interactions of the c-f bond: The crystallographic environment of fluorinated carboxylic acids and related structures
    • Murray-Rust P, Stallings WC, Monti CT, Preston RK, Glusker JP (1983) Intermolecular interactions of the C-F Bond: the crystallographic environment of fluorinated carboxylic acids and related structures. J Am Chem Soc 105:3206–3214
    • (1983) J am Chem Soc , vol.105 , pp. 3206-3214
    • Murray-Rust, P.1    Stallings, W.C.2    Monti, C.T.3    Preston, R.K.4    Glusker, J.P.5
  • 133
    • 80054118874 scopus 로고    scopus 로고
    • Nh + −f hydrogen-bonding in a fluorinated “proton sponge” derivative: Integration of solution, solid-state, gas-phase, and computational studies
    • Scerba MT, Leavitt CM, Diener ME, DeBlase AF, Guasco TL, Siegler MA, Bair N, Johnson MA, Lectka T (2011) NH + −F hydrogen-bonding in a fluorinated “Proton Sponge” derivative: integration of solution, solid-state, gas-phase, and computational studies. J Org Chem 76:7975–7984
    • (2011) J Org Chem , vol.76 , pp. 7975-7984
    • Scerba, M.T.1    Leavitt, C.M.2    Diener, M.E.3    DeBlase, A.F.4    Guasco, T.L.5    Siegler, M.A.6    Bair, N.7    Johnson, M.A.8    Lectka, T.9
  • 134
    • 82455205702 scopus 로고    scopus 로고
    • On the nature of c-h⋯f-c interactions in hindered cf3 -c(Sp 3) bond rotations
    • Prakash GKS, Wang F, Rahm M, Shen J, Ni C, Haiges R, Olah GA (2011) On the nature of C-H⋯F-C interactions in hindered CF3 -C(sp3) bond rotations. Angew Chem Int Ed 50:11761–11764
    • (2011) Angew Chem Int Ed , vol.50 , pp. 11761-11764
    • Prakash, G.1    Wang, F.2    Rahm, M.3    Shen, J.4    Ni, C.5    Haiges, R.6    Olah, G.A.7
  • 135
    • 84858023003 scopus 로고    scopus 로고
    • Is organic fluorine really “not” polarizable?
    • Chopra D (2012) Is organic fluorine really “not” polarizable? Cryst Growth Des 12:541–546
    • (2012) Cryst Growth Des , vol.12 , pp. 541-546
    • Chopra, D.1
  • 136
    • 4544278491 scopus 로고    scopus 로고
    • Organic fluorine: Odd man out
    • Dunitz JD (2004) Organic fluorine: odd man out. ChemBioChem 5:614–621
    • (2004) Chembiochem , vol.5 , pp. 614-621
    • Dunitz, J.D.1
  • 137
    • 84862976181 scopus 로고    scopus 로고
    • The fho intramolecular hydrogen bond forming five-membered rings hardly appear in monocyclic organofluorine compounds
    • Cormanich RA, Freitas MP, Tormena CF, Rittner R (2012) The FHO intramolecular hydrogen bond forming five-membered rings hardly appear in monocyclic organofluorine compounds. RSC Adv 2:4169–4174
    • (2012) RSC Adv , vol.2 , pp. 4169-4174
    • Cormanich, R.A.1    Freitas, M.P.2    Tormena, C.F.3    Rittner, R.4
  • 138
    • 0030937244 scopus 로고    scopus 로고
    • Organic fluorine hardly ever accepts hydrogen bonds
    • Dunitz JD, Taylor R (1997) Organic fluorine hardly ever accepts hydrogen bonds. Chem Eur J 3:89–98
    • (1997) Chem Eur J , vol.3 , pp. 89-98
    • Dunitz, J.D.1    Taylor, R.2
  • 139
    • 84864277924 scopus 로고    scopus 로고
    • F⋯ho intramolecular hydrogen bond as the main transmission mechanism for 1h j f, h(O) coupling constant in 2′-fluorofl avonol
    • Fonseca TAO, Ramalho TC, Freitas MP (2012) F⋯HO intramolecular hydrogen bond as the main transmission mechanism for 1h J F, H(O) coupling constant in 2′-fluorofl avonol. Magn Reson Chem 50:551–556
    • (2012) Magn Reson Chem , vol.50 , pp. 551-556
    • Fonseca, T.1    Ramalho, T.C.2    Freitas, M.P.3
  • 142
    • 33750876492 scopus 로고    scopus 로고
    • Fluorine-18 and medical imaging: Radiopharmaceuticals for positron emission tomography
    • Le Bars D (2006) Fluorine-18 and medical imaging: radiopharmaceuticals for positron emission tomography. J Fluor Chem 127:1488–1493
    • (2006) J Fluor Chem , vol.127 , pp. 1488-1493
    • Le Bars, D.1
  • 143
    • 56249122581 scopus 로고    scopus 로고
    • Synthesis of 11c, 18f, 15o and 13n radiolabels for positron emission tomography
    • Miller PW, Long NJ, Vilar R, Gee AD (2008) Synthesis of 11C, 18F, 15O and 13N radiolabels for positron emission tomography. Angew Chem Int Ed 47:8998–9033
    • (2008) Angew Chem Int Ed , vol.47 , pp. 8998-9033
    • Miller, P.W.1    Long, N.J.2    Vilar, R.3    Gee, A.D.4
  • 145
    • 0036660195 scopus 로고    scopus 로고
    • Fluorine-18-radiolabeled pharmaceuticals for imaging with positron emission tomography, excluding [18f]-fluorodeoxyglucose
    • Pauwels EKJ, van der Klaauw AA, Corporaal T, Stokkel MPM (2002) Fluorine-18-radiolabeled pharmaceuticals for imaging with positron emission tomography, excluding [18F]-fluorodeoxyglucose. Drugs Future 27:655–667
    • (2002) Drugs Future , vol.27 , pp. 655-667
    • Pauwels, E.1    Van Der Klaauw, A.A.2    Corporaal, T.3    Stokkel, M.4
  • 147
    • 47149106805 scopus 로고    scopus 로고
    • Synthesis and sar of a mglur5 allosteric partial antagonist lead: Unexpected modulation of pharmacology with slight structural modifications to a 5-(phenylethynyl)pyrimidine scaffold
    • Sharma S, Rodriguez AL, Conn PJ, Lindsley CW (2008) Synthesis and SAR of a mGluR5 allosteric partial antagonist lead: unexpected modulation of pharmacology with slight structural modifications to a 5-(phenylethynyl)pyrimidine scaffold. Bioorg Med Chem Lett 18:4098–4101
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 4098-4101
    • Sharma, S.1    Rodriguez, A.L.2    Conn, P.J.3    Lindsley, C.W.4
  • 148
    • 79956119128 scopus 로고    scopus 로고
    • Efficacy switching sar of mglur5 allosteric modulators: Highly potent positive and negative modulators from one chemotype
    • Sams AG, Mikkelsen AK, Brodbeck RMG, Pu X, Ritzén A (2011) Efficacy switching SAR of mGluR5 allosteric modulators: highly potent positive and negative modulators from one chemotype. Bioorg Med Chem Lett 21:3407–3410
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 3407-3410
    • Sams, A.G.1    Mikkelsen, A.K.2    Brodbeck, R.3    Pu, X.4    Ritzén, A.5
  • 151
    • 36749084187 scopus 로고    scopus 로고
    • Recent developments and trends in 18 f-radiochemistry: Syntheses and applications
    • Schirrmacher R, Wängler C, Schirrmacher E (2007) Recent developments and trends in 18 F-radiochemistry: syntheses and applications. Mini Rev Org Chem 4:317–329
    • (2007) Mini Rev Org Chem , vol.4 , pp. 317-329
    • Schirrmacher, R.1    Wängler, C.2    Schirrmacher, E.3
  • 152
    • 49849087072 scopus 로고    scopus 로고
    • Chemistry with [18f]-fluoride ion
    • Cai L, Lu S, Pike VW (2008) Chemistry with [18F]-fluoride ion. Eur J Org Chem 2853–2873
    • (2008) Eur J Org Chem , pp. 2853-2873
    • Cai, L.1    Lu, S.2    Pike, V.W.3
  • 153
    • 84856194256 scopus 로고    scopus 로고
    • Novel strategies for fluorine-18 radiochemistry
    • Littich R, Scott PJH (2012) Novel strategies for fluorine-18 radiochemistry. Angew Chem Int Ed 51:1106–1109
    • (2012) Angew Chem Int Ed , vol.51 , pp. 1106-1109
    • Littich, R.1    Scott, P.2
  • 154
    • 84857522998 scopus 로고    scopus 로고
    • Transition metal catalysis and nucleophilic fluorination
    • Hollingworth C, Gouverneur V (2012) Transition metal catalysis and nucleophilic fluorination. Chem Commun 48:2929–2942
    • (2012) Chem Commun , vol.48 , pp. 2929-2942
    • Hollingworth, C.1    Gouverneur, V.2
  • 155
    • 54549116946 scopus 로고    scopus 로고
    • Novel nucleophilic and electrophilic fluoroalkylation methods
    • Prakash GKS, Chacko S (2008) Novel nucleophilic and electrophilic fluoroalkylation methods. Curr Opin Drug Discov Dev 11:793–802
    • (2008) Curr Opin Drug Discov Dev , vol.11 , pp. 793-802
    • Prakash, G.1    Chacko, S.2
  • 156
    • 11844274689 scopus 로고    scopus 로고
    • Modern synthetic methods for fluorine-substituted target molecules
    • Shimizu M, Hiyama T (2004) Modern synthetic methods for fluorine-substituted target molecules. Angew Chem Int Ed 44:214–231
    • (2004) Angew Chem Int Ed , vol.44 , pp. 214-231
    • Shimizu, M.1    Hiyama, T.2
  • 157
    • 46149094509 scopus 로고    scopus 로고
    • Fluorination in medicinal chemistry: Methods, strategies, and recent developments
    • Kirk KL (2008) Fluorination in medicinal chemistry: methods, strategies, and recent developments. Org Proc Res Dev 12:305–321
    • (2008) Org Proc Res Dev , vol.12 , pp. 305-321
    • Kirk, K.L.1
  • 159
    • 0034768552 scopus 로고    scopus 로고
    • 18
    • Pauwels EKJ (2001) 18F-Labeled fluorodeoxyglucose for PET imaging: the working mechanism and its clinical implication. Drugs Future 26:659–668
    • (2001) Drugs Future , vol.26 , pp. 659-668
    • Pauwels, E.1
  • 161
    • 0042848538 scopus 로고    scopus 로고
    • Imaging studies of biodistribution and kinetics in drug development
    • Berridge MS, Heald DL, Lee Z (2003) Imaging studies of biodistribution and kinetics in drug development. Drug Dev Res 59:208–226
    • (2003) Drug Dev Res , vol.59 , pp. 208-226
    • Berridge, M.S.1    Heald, D.L.2    Lee, Z.3
  • 162
    • 78649479373 scopus 로고    scopus 로고
    • Radiolabeled small molecule protein kinase inhibitors for imaging with pet or spect
    • Hicks JW, Van Brocklin HF, Wilson AA, Houle S, Vasdev N (2010) Radiolabeled small molecule protein kinase inhibitors for imaging with PET or SPECT. Molecules 15:8260–8278
    • (2010) Molecules , vol.15 , pp. 8260-8278
    • Hicks, J.W.1    Van Brocklin, H.F.2    Wilson, A.A.3    Houle, S.4    Vasdev, N.5
  • 163
    • 79955660274 scopus 로고    scopus 로고
    • Neurotransmitter imaging: Basic concepts and future perspectives
    • Badgaiyan RD (2011) Neurotransmitter imaging: basic concepts and future perspectives. Curr Med Imaging Rev 7:98–103
    • (2011) Curr Med Imaging Rev , vol.7 , pp. 98-103
    • Badgaiyan, R.D.1
  • 164
    • 42049120081 scopus 로고    scopus 로고
    • 6-l- 18f-fluorodihydroxyphenylalanine pet in neuroendocrine tumors: Basic aspects and emerging clinical applications
    • Jager PL, Chirakal R, Marriott CJ, Brouwers AH, Koopmans KP, Gulenchyn KY (2008) 6-L- 18F-fluorodihydroxyphenylalanine PET in neuroendocrine tumors: basic aspects and emerging clinical applications. J Nucl Med 49:573–586
    • (2008) J Nucl Med , vol.49 , pp. 573-586
    • Jager, P.L.1    Chirakal, R.2    Marriott, C.J.3    Brouwers, A.H.4    Koopmans, K.P.5    Gulenchyn, K.Y.6
  • 166
    • 0021083984 scopus 로고
    • Dopamine visualized in the basal ganglia of living man
    • Garnett ES, Firnau G, Nahmias C (1983) Dopamine visualized in the basal ganglia of living man. Nature 305:137–138
    • (1983) Nature , vol.305 , pp. 137-138
    • Garnett, E.S.1    Firnau, G.2    Nahmias, C.3
  • 167
    • 0042848536 scopus 로고    scopus 로고
    • Positron-labeled dopa analogs to image dopamine terminals
    • DeJesus OT (2003) Positron-labeled DOPA analogs to image dopamine terminals. Drug Dev Res 59:249–260
    • (2003) Drug Dev Res , vol.59 , pp. 249-260
    • DeJesus, O.T.1
  • 170
    • 33746472882 scopus 로고    scopus 로고
    • Pet tracers for imaging of the dopaminergic system
    • Elsinga PH, Hatano K, Ishiwata K (2006) PET tracers for imaging of the dopaminergic system. Curr Med Chem 13:2139–2153
    • (2006) Curr Med Chem , vol.13 , pp. 2139-2153
    • Elsinga, P.H.1    Hatano, K.2    Ishiwata, K.3
  • 173
    • 0026355999 scopus 로고
    • Fluorine-18- altanserin: A radioligand for the study of serotonin receptors with pet: Radiolabeling and in vivo biologic behavior in rats
    • Lemaire C, Cantineau R, Marcel Guillaume M, Plenevaux A, Christiaens L (1991) Fluorine-18- altanserin: a radioligand for the study of serotonin receptors with PET: radiolabeling and in vivo biologic behavior in rats. J Nucl Med 32:2266–2272
    • (1991) J Nucl Med , vol.32 , pp. 2266-2272
    • Lemaire, C.1    Cantineau, R.2    Marcel Guillaume, M.3    Plenevaux, A.4    Christiaens, L.5
  • 174
    • 64049085375 scopus 로고    scopus 로고
    • Synthesis and in vitro affinities of various mdl 100907 derivatives as potential 18f-radioligands for 5-ht 2a receptor imaging with pet
    • Herth MM, Kramer V, Piel M, Palner M, Riss PJ, Knudsen GM, Roesch F (2009) Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT 2A receptor imaging with PET. Bioorg Med Chem 17:2989–3002
    • (2009) Bioorg Med Chem , vol.17 , pp. 2989-3002
    • Herth, M.M.1    Kramer, V.2    Piel, M.3    Palner, M.4    Riss, P.J.5    Knudsen, G.M.6    Roesch, F.7
  • 175
    • 49449109015 scopus 로고    scopus 로고
    • Discovery of (−)-7-methyl-2-exo-[3′-(6-[ 18 f] fluoropyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptane, a radiolabeled antagonist for cerebral nicotinic acetylcholine receptor (α4β2-nachr) with optimal positron emission tomography imaging properties
    • Gao Y, Kuwabara H, Spivak CE, Xiao Y, Kellar K, Ravert HT, Kumar A, Alexander M, Hilton J, Wong DF, Dannals RF, Horti AG (2008) Discovery of (−)-7-methyl-2-exo-[3′-(6-[ 18 F] fluoropyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptane, a radiolabeled antagonist for cerebral nicotinic acetylcholine receptor (α4β2-nAChR) with optimal positron emission tomography imaging properties. J Med Chem 51:4751–4764
    • (2008) J Med Chem , vol.51 , pp. 4751-4764
    • Gao, Y.1    Kuwabara, H.2    Spivak, C.E.3    Xiao, Y.4    Kellar, K.5    Ravert, H.T.6    Kumar, A.7    Alexander, M.8    Hilton, J.9    Wong, D.F.10    Dannals, R.F.11    Horti, A.G.12
  • 176
    • 84865683216 scopus 로고    scopus 로고
    • Brain amyloid imaging – fda approval of fl orbetapir f18 injection
    • Yang L, Rieves D, Ganley C (2012) Brain amyloid imaging – FDA approval of fl orbetapir F18 injection. New Engl J Med 367:885–887
    • (2012) New Engl J Med , vol.367 , pp. 885-887
    • Yang, L.1    Rieves, D.2    Ganley, C.3
  • 177
    • 84871883065 scopus 로고    scopus 로고
    • First fda-approved beta-amyloid diagnostic hits the market
    • Garber K (2012) First FDA-approved beta-amyloid diagnostic hits the market. Nat Biotechnol 30:575
    • (2012) Nat Biotechnol , vol.30 , pp. 575
    • Garber, K.1
  • 178
  • 180
    • 24944586305 scopus 로고    scopus 로고
    • F-18 stilbenes as pet imaging agents for detecting β-amyloid plaques in the brain
    • Wang W, Oya S, Kung MP, Hou C, Maier DL, Kung HF (2005) F-18 stilbenes as PET imaging agents for detecting β-amyloid plaques in the brain. J Med Chem 48:5980–5988
    • (2005) J Med Chem , vol.48 , pp. 5980-5988
    • Wang, W.1    Oya, S.2    Kung, M.P.3    Hou, C.4    Maier, D.L.5    Kung, H.F.6
  • 181
    • 34247637096 scopus 로고    scopus 로고
    • Novel styrylpyridines as probes for spect imaging of amyloid plaques
    • Qu W, Kung MP, Hou C, Benedum TE, Kung HF (2007) Novel styrylpyridines as probes for SPECT imaging of amyloid plaques. J Med Chem 50:2157–2165
    • (2007) J Med Chem , vol.50 , pp. 2157-2165
    • Qu, W.1    Kung, M.P.2    Hou, C.3    Benedum, T.E.4    Kung, H.F.5
  • 182
    • 27144437223 scopus 로고    scopus 로고
    • F-18f peg stilbenes as pet imaging agents targeting aβ aggregates in the brain
    • Zhang W, Oyas S, Kung MP, Hou C, Maier DL, Kung HF (2005) F-18F PEG stilbenes as PET imaging agents targeting Aβ aggregates in the brain. Nucl Med Biol 32:799–809
    • (2005) Nucl Med Biol , vol.32 , pp. 799-809
    • Zhang, W.1    Oyas, S.2    Kung, M.P.3    Hou, C.4    Maier, D.L.5    Kung, H.F.6
  • 193
    • 84876876010 scopus 로고    scopus 로고
    • An in vivo evaluation of cerebral cortical amyloid with 18 f-flutemetamol using positron emission tomography compared with parietal biopsy samples in living normal pressure hydrocephalus patients
    • Wong DF, Moghekar Abhay R, Rigamonti D, Brasic JR, Rousset O, Willis W, Buckley C, Smith A, Gok B, Sherwin P, Grachev ID (2013) An in vivo evaluation of cerebral cortical amyloid with 18 F-flutemetamol using positron emission tomography compared with parietal biopsy samples in living normal pressure hydrocephalus patients. Mol Imaging Biol 15: 230–237
    • (2013) Mol Imaging Biol , vol.15 , pp. 230-237
    • Wong, D.F.1    Moghekar Abhay, R.2    Rigamonti, D.3    Brasic, J.R.4    Rousset, O.5    Willis, W.6    Buckley, C.7    Smith, A.8    Gok, B.9    Sherwin, P.10    Grachev, I.D.11
  • 197
    • 78649320159 scopus 로고    scopus 로고
    • Radiopharmaceutical chemistry for positron emission tomography
    • Li Z, Conti PS (2010) Radiopharmaceutical chemistry for positron emission tomography. Adv Drug Deliv Rev 62:1031–1051
    • (2010) Adv Drug Deliv Rev , vol.62 , pp. 1031-1051
    • Li, Z.1    Conti, P.S.2
  • 198
    • 84865012022 scopus 로고    scopus 로고
    • Direct, nucleophilic radiosynthesis of [18f]-trifluoroalkyl tosylates: Improved labelling procedures
    • Riss PJ, Ferrari V, Brichard L, Burke P, Smith R, Aigbirhio FI (2012) Direct, nucleophilic radiosynthesis of [18F]-trifluoroalkyl tosylates: improved labelling procedures. Org Biomol Chem 10:6980–6986
    • (2012) Org Biomol Chem , vol.10 , pp. 6980-6986
    • Riss, P.J.1    Ferrari, V.2    Brichard, L.3    Burke, P.4    Smith, R.5    Aigbirhio, F.I.6
  • 199
    • 84863145433 scopus 로고    scopus 로고
    • Facile aromatic radiofluorination of [18f]-fl umazenil from diaryliodonium slats with evaluation of their stability and selectivity
    • Moon BS, Kil HS, Park JH, Kim JS, Park J, Chi DY, Lee BC, Kim SE (2011) Facile aromatic radiofluorination of [18F]-fl umazenil from diaryliodonium slats with evaluation of their stability and selectivity. Org Biomol Chem 9:8346–8355
    • (2011) Org Biomol Chem , vol.9 , pp. 8346-8355
    • Moon, B.S.1    Kil, H.S.2    Park, J.H.3    Kim, J.S.4    Park, J.5    Chi, D.Y.6    Lee, B.C.7    Kim, S.E.8
  • 201
    • 84866068267 scopus 로고    scopus 로고
    • Oxidative aliphatic c-h fluorination with fluoride ion catalyzed by a manganese porphyrin
    • Liu W, Huang X, Cheng M-J, Nielsen RJ, Goddard WA III, Groves JT (2012) Oxidative aliphatic C-H fluorination with fluoride ion catalyzed by a manganese porphyrin. Science 337:1322–1325
    • (2012) Science , vol.337 , pp. 1322-1325
    • Liu, W.1    Huang, X.2    Cheng, M.-J.3    Nielsen, R.J.4    Goddard, W.5    Groves, J.T.6


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