메뉴 건너뛰기




Volumn 47, Issue 21, 2004, Pages 5114-5125

Hydrogen bonding interactions of covalently bonded fluorine atoms: From crystallographic data to a new angular function in the GRID force field

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE;

EID: 4744373354     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0498349     Document Type: Article
Times cited : (220)

References (37)
  • 1
    • 4744359480 scopus 로고    scopus 로고
    • MDL Drug Data Report is available from Molecular Design Limited Information Systems, Inc., 14600 Catalina St., San Leandro, CA 94577
    • MDL Drug Data Report is available from Molecular Design Limited Information Systems, Inc., 14600 Catalina St., San Leandro, CA 94577.
  • 2
    • 0035821596 scopus 로고    scopus 로고
    • Simple Selection Criteria for Drug-like Chemical Matter
    • Muegge, I.; Heald, S. L.; Brittelli, D. Simple Selection Criteria for Drug-like Chemical Matter. J. Med. Chem. 2001, 44, 1841-1846.
    • (2001) J. Med. Chem. , vol.44 , pp. 1841-1846
    • Muegge, I.1    Heald, S.L.2    Brittelli, D.3
  • 4
    • 0042921620 scopus 로고    scopus 로고
    • Fluorine Substitution Can Block CYP3A4 Metabolism-Dependent Inhibition: Identification of (S)-N-[1-(4-Fluoro-3-morpholin-4-ylphenyl)ethyl]-3-(4- fluorophenyl)acrylamide as an Orally Bioavailable KCNQ2 Opener Devoid of CYP3A4 Metabolism-Dependent Inhibition
    • Wu, Y.-J.; Davis, C. D.; Dworetzky, S.; Fitzpatrick, W. C.; Harden, D.; He, H.; Knox, R. J.; Newton, A. E.; Philip, T.; Poison, C.; Sivarao, D. V.; Sun, L.-Q.; Tertyshnikova, S.; Weaver, D.; Yeola, S.; Zoeckler, M.; Sinz, M. W. Fluorine Substitution Can Block CYP3A4 Metabolism-Dependent Inhibition: Identification of (S)-N-[1-(4-Fluoro-3-morpholin-4-ylphenyl)ethyl]-3-(4- fluorophenyl)acrylamide as an Orally Bioavailable KCNQ2 Opener Devoid of CYP3A4 Metabolism-Dependent Inhibition. J. Med. Chem. 2003, 46, 3778-3781.
    • (2003) J. Med. Chem. , vol.46 , pp. 3778-3781
    • Wu, Y.-J.1    Davis, C.D.2    Dworetzky, S.3    Fitzpatrick, W.C.4    Harden, D.5    He, H.6    Knox, R.J.7    Newton, A.E.8    Philip, T.9    Poison, C.10    Sivarao, D.V.11    Sun, L.-Q.12    Tertyshnikova, S.13    Weaver, D.14    Yeola, S.15    Zoeckler, M.16    Sinz, M.W.17
  • 5
    • 0038440502 scopus 로고    scopus 로고
    • Predicting Drug Metabolism: A Site of Metabolism Prediction Tool Applied to the Cytochrome P450 2C9
    • Zamora, I.; Afzelius, L.; Cruciani, G. Predicting Drug Metabolism: A Site of Metabolism Prediction Tool Applied to the Cytochrome P450 2C9. J. Med. Chem. 2003, 46, 2313-2324.
    • (2003) J. Med. Chem. , vol.46 , pp. 2313-2324
    • Zamora, I.1    Afzelius, L.2    Cruciani, G.3
  • 7
    • 0029975253 scopus 로고    scopus 로고
    • Metabolism and structure activity data based drug design: Discovery of (-) SCH 53079 an analog of the potent cholesterol absorption inhibitor (-) SCH 48461
    • Dugar, S.; Yumibe, N.; Clader, J. W.; Vizziano, M.; Huie, K.; Van Heek, M.; Compton, D. S.: Davis Jr. H. R. Metabolism and structure activity data based drug design: discovery of (-) SCH 53079 an analog of the potent cholesterol absorption inhibitor (-) SCH 48461. Biorg. Med. Chem. Lett. 1996, 6, 1271-1274.
    • (1996) Biorg. Med. Chem. Lett. , vol.6 , pp. 1271-1274
    • Dugar, S.1    Yumibe, N.2    Clader, J.W.3    Vizziano, M.4    Huie, K.5    Van Heek, M.6    Compton, D.S.7    Davis Jr., H.R.8
  • 8
    • 0000255059 scopus 로고
    • The relative strengths of alkyl halides as proton acceptor groups in hydrogen bonding
    • West, R.; Powell, D. L.; Whatley, L. S.; Lee, M. K. T.; Schleyer, P.von R. The relative strengths of alkyl halides as proton acceptor groups in hydrogen bonding. J. Am. Chem. Soc. 1962, 84, 3221-3222.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 3221-3222
    • West, R.1    Powell, D.L.2    Whatley, L.S.3    Lee, M.K.T.4    Schleyer, P.V.R.5
  • 9
    • 1842663065 scopus 로고    scopus 로고
    • Some influences of fluorine in bioorganic chemistry
    • O'Hagan, D. Rzepa, H. S. Some influences of fluorine in bioorganic chemistry. Chem. Commun. 1997, 645-652.
    • (1997) Chem. Commun. , pp. 645-652
    • O'Hagan, D.1    Rzepa, H.S.2
  • 10
    • 0004524514 scopus 로고
    • Intermolecular Interactions of the C-F Bond: The Crystallographic Environment of Fluorinated Carboxylic Acids and Related Structures
    • Murray-Rust, P.; Stallings, W. C.; Monti, C. T.; Preston, R. K.; Glusker, J. P. Intermolecular Interactions of the C-F Bond: The Crystallographic Environment of Fluorinated Carboxylic Acids and Related Structures. J. Am. Chem. Soc. 1983, 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
  • 11
    • 0000243556 scopus 로고    scopus 로고
    • Understanding the Behaviour of Halogens as Hydrogen Bond Acceptors
    • Brammer, L.; Bruton, E. A.; Sherwood, P. Understanding the Behaviour of Halogens as Hydrogen Bond Acceptors. Cryst. Growth Des. 2001, 1, 277-290.
    • (2001) Cryst. Growth Des. , vol.1 , pp. 277-290
    • Brammer, L.1    Bruton, E.A.2    Sherwood, P.3
  • 12
    • 0001567416 scopus 로고    scopus 로고
    • Hydrogen-bond distances to halide ions and organometallic crystal structures: Up-to-date database study
    • Stainer, T. Hydrogen-bond distances to halide ions and organometallic crystal structures: up-to-date database study. Acta Crystallogr. 1998, B54, 456-563.
    • (1998) Acta Crystallogr. , vol.B54 , pp. 456-563
    • Stainer, T.1
  • 13
    • 0002678466 scopus 로고    scopus 로고
    • 3) hydrogen bonding interactions in the solid state
    • 3) hydrogen bonding interactions in the solid state. J. Chem. Soc., Perkin Trans. 2 1997, 1999-2001.
    • (1997) J. Chem. Soc., Perkin Trans. 2 , pp. 1999-2001
    • Mascal, M.1
  • 14
    • 0001043187 scopus 로고
    • Halide anions as proton acceptors in hydrogen bonding
    • Allerhand, A.; Scheleyer, P. von R. Halide anions as proton acceptors in hydrogen bonding. J. Am. Chem. Soc. 1983, 85, 1233-1237.
    • (1983) J. Am. Chem. Soc. , vol.85 , pp. 1233-1237
    • Allerhand, A.1    Scheleyer, P.V.R.2
  • 15
    • 0001767081 scopus 로고
    • Strong Hydrogen Bonds. II. The Hydrogen Difluoride Ion
    • Harbell, S. A.; McDaniel, D. H. Strong Hydrogen Bonds. II. The Hydrogen Difluoride Ion. J. Am. Chem. Soc. 1984, 86, 4497-4497.
    • (1984) J. Am. Chem. Soc. , vol.86 , pp. 4497-4497
    • Harbell, S.A.1    McDaniel, D.H.2
  • 16
    • 0032721272 scopus 로고    scopus 로고
    • Fluoride Ligands exhibit marked departures from the hydrogen bond acceptor of their heavier halogen congeners
    • Brammer, L.; Bruton, E. A.; Sherwood, P. Fluoride Ligands exhibit marked departures from the hydrogen bond acceptor of their heavier halogen congeners. New J. Chem. 1999, 23, 965-968.
    • (1999) New J. Chem. , vol.23 , pp. 965-968
    • Brammer, L.1    Bruton, E.A.2    Sherwood, P.3
  • 17
    • 0034067901 scopus 로고    scopus 로고
    • Observations on the strength of hydrogen bonding
    • Laurence, C.; Berthelot, M. Observations on the strength of hydrogen bonding. Persp. Drug Discovery Des. 2000, 1, 39-60.
    • (2000) Persp. Drug Discovery Des. , vol.1 , pp. 39-60
    • Laurence, C.1    Berthelot, M.2
  • 18
    • 0001589890 scopus 로고    scopus 로고
    • The first basicity scale of fluoro-, chloro,-, bromo- and iodo-alkanes: Some cross-comparison with simple alkyl derivatives of other elements
    • Ouvrard, C.; Berthelot, M.; Laurence, C. The first basicity scale of fluoro-, chloro,-, bromo- and iodo-alkanes: some cross-comparison with simple alkyl derivatives of other elements. J. Chem. Soc., Perkin Trans. 2 1999, 1357-1362.
    • (1999) J. Chem. Soc., Perkin Trans. 2 , pp. 1357-1362
    • Ouvrard, C.1    Berthelot, M.2    Laurence, C.3
  • 19
    • 0030590426 scopus 로고    scopus 로고
    • How Good is Fluorine as a Hydrogen Bond Acceptor?
    • Howard, J. A. K.; Hoy, V. J.; O'Hagan, D.; Smith, G. T. How Good is Fluorine as a Hydrogen Bond Acceptor? Tetrahedron 1998, 52, 12613-12622.
    • (1998) Tetrahedron , vol.52 , pp. 12613-12622
    • Howard, J.A.K.1    Hoy, V.J.2    O'Hagan, D.3    Smith, G.T.4
  • 21
    • 0000473838 scopus 로고
    • The Geometry of Intermolecular Interactions in Some Crystalline Fluorine-Containing Organic Compounds
    • Shimoni, L.; Glusker, J. P. The Geometry of Intermolecular Interactions in Some Crystalline Fluorine-Containing Organic Compounds. Struct. Chem. 1994, 5, 383-397.
    • (1994) Struct. Chem. , vol.5 , pp. 383-397
    • Shimoni, L.1    Glusker, J.P.2
  • 22
    • 0030937244 scopus 로고    scopus 로고
    • Organic Fluorine Hardly Ever Accepts Hydrogens Bonds
    • Dunitz, J. D.; Taylor, R. Organic Fluorine Hardly Ever Accepts Hydrogens Bonds. Chem. Eur. J. 1997, 3, 89-98.
    • (1997) Chem. Eur. J. , vol.3 , pp. 89-98
    • Dunitz, J.D.1    Taylor, R.2
  • 24
    • 4744339076 scopus 로고    scopus 로고
    • http://www.rcsb.org/pdb/
  • 25
    • 0021871375 scopus 로고
    • A Computational Procedure for Determining Energetically Favorable Binding Sites on Biologically Important Macromolecules
    • Goodford, P. J. A Computational Procedure for Determining Energetically Favorable Binding Sites on Biologically Important Macromolecules. J. Med. Chem. 1985, 28, 849-857.
    • (1985) J. Med. Chem. , vol.28 , pp. 849-857
    • Goodford, P.J.1
  • 26
    • 4744375119 scopus 로고    scopus 로고
    • The version 22 of the GRID package is available from Molecular Discovery Ltd., 4, Chandos Street, W1A 3BQ, London, United Kingdom
    • The version 22 of the GRID package is available from Molecular Discovery Ltd., 4, Chandos Street, W1A 3BQ, London, United Kingdom. http://www. moldiscovery.com
  • 27
    • 0001426349 scopus 로고    scopus 로고
    • A Cambridge Structural Database analysis of the C-H⋯Cl interaction: C-H⋯Cl- and C-H⋯Cl-M often behave as hydrogen bonds but C-H⋯-Cl-C is generally a van der Waals interaction
    • Thallypally, P. K.; Nangia, A. A Cambridge Structural Database analysis of the C-H⋯Cl interaction: C-H⋯Cl- and C-H⋯Cl-M often behave as hydrogen bonds but C-H⋯Cl-C is generally a van der Waals interaction. Cryst. Eng. Commun. 2001, 3, 114-119.
    • (2001) Cryst. Eng. Commun. , vol.3 , pp. 114-119
    • Thallypally, P.K.1    Nangia, A.2
  • 29
    • 20544433165 scopus 로고
    • Van der Waals Volumes and Radii
    • Bondi, A. van der Waals Volumes and Radii. J. Phys. Chem. 1984, 68, 441-451.
    • (1984) J. Phys. Chem. , vol.68 , pp. 441-451
    • Bondi, A.1
  • 30
    • 0005826466 scopus 로고    scopus 로고
    • Tripos Inc., 1699 South Hanley Rd., St. Louis, Missouri, 63144
    • SYBYL 6.7, Tripos Inc., 1699 South Hanley Rd., St. Louis, Missouri, 63144.
    • SYBYL 6.7
  • 31
    • 0024566942 scopus 로고
    • New Hydrogen-Bond Potentials for Use in Determining Energetically Favorable Binding Sites on Molecules of Known Structure
    • Boobbyer, D. N. A.; Goodford, P. J.; McWhinnie, P. M.; Wade, R. C. New Hydrogen-Bond Potentials for Use in Determining Energetically Favorable Binding Sites on Molecules of Known Structure. J. Med. Chem. 1989, 32, 1083-1094.
    • (1989) J. Med. Chem. , vol.32 , pp. 1083-1094
    • Boobbyer, D.N.A.1    Goodford, P.J.2    McWhinnie, P.M.3    Wade, R.C.4
  • 32
    • 0027439587 scopus 로고
    • Further Development of Hydrogen Bond Functions for Use in Determining Energetically Favorable Binding Sites on Molecules of Known Structure. 1. Ligand Probe Groups with the Ability to Form Two Hydrogen Bonds
    • Wade, R. C.; Clark, K. J.; Goodford, P. J. Further Development of Hydrogen Bond Functions for Use in Determining Energetically Favorable Binding Sites on Molecules of Known Structure. 1. Ligand Probe Groups with the Ability to Form Two Hydrogen Bonds. J. Med. Chem. 1993, 36, 140-147.
    • (1993) J. Med. Chem. , vol.36 , pp. 140-147
    • Wade, R.C.1    Clark, K.J.2    Goodford, P.J.3
  • 33
    • 0027510004 scopus 로고
    • Further Development of Hydrogen Bond Functions for Use in Determining Energetically Favorable Binding Sites on Molecules of Known Structure. 2. Ligand Probe Groups with the Ability to Form More Than Two Hydrogen Bonds
    • Wade, R. C.; Goodford, P. J. Further Development of Hydrogen Bond Functions for Use in Determining Energetically Favorable Binding Sites on Molecules of Known Structure. 2. Ligand Probe Groups with the Ability to Form More Than Two Hydrogen Bonds. J. Med. Chem. 1993, 36, 148-156.
    • (1993) J. Med. Chem. , vol.36 , pp. 148-156
    • Wade, R.C.1    Goodford, P.J.2
  • 34
    • 0026720426 scopus 로고
    • Crystallographic Analysis of Transition State Mimics Bound to Penillopepsin: Difluorostatine- and Difluorostatone-Containing Peptides
    • James, M. N. G.; Sielecki, A. R.; Hayakawa, K.; Gelb, M. H. Crystallographic Analysis of Transition State Mimics Bound to Penillopepsin: Difluorostatine- and Difluorostatone-Containing Peptides. Biochemistry 1992, 31, 3872-3886.
    • (1992) Biochemistry , vol.31 , pp. 3872-3886
    • James, M.N.G.1    Sielecki, A.R.2    Hayakawa, K.3    Gelb, M.H.4
  • 35
    • 0024974079 scopus 로고
    • Crystallographic Analysis of the Inhibition of Porcine Pancreatic Elastase by a Peptidyl Boronic Acid: Structure of a Reaction Intermediate
    • Takahashi, L. H.; Radhakrishnan, R.; Rosenfield, R. E.; Meyer, Jr. E. F. Crystallographic Analysis of the Inhibition of Porcine Pancreatic Elastase by a Peptidyl Boronic Acid: Structure of a Reaction Intermediate. Biochemistry 1989, 28, 7610-7617.
    • (1989) Biochemistry , vol.28 , pp. 7610-7617
    • Takahashi, L.H.1    Radhakrishnan, R.2    Rosenfield, R.E.3    Meyer Jr., E.F.4
  • 36
    • 34547119107 scopus 로고
    • Nonlinearity of hydrogen bonds in molecular crystals
    • Kroon, J.; Kanters, J. A. Nonlinearity of hydrogen bonds in molecular crystals. Nature 1974, 248, 667-668.
    • (1974) Nature , vol.248 , pp. 667-668
    • Kroon, J.1    Kanters, J.A.2
  • 37
    • 0035964325 scopus 로고    scopus 로고
    • Structural Characterization of the Enzyme-Substrate, Enzyme-Intermediate, and Enzyme-Product Complexes of Thiamin Phosphate Synthase
    • Peapus, D. H.; Chiu, H.-J.; Campobasso, N.; Reddick, J. J.; Begley, T. P.; Ealick, S. E. Structural Characterization of the Enzyme-Substrate, Enzyme-Intermediate, and Enzyme-Product Complexes of Thiamin Phosphate Synthase. Biochemistry 2001, 40, 10103-10114.
    • (2001) Biochemistry , vol.40 , pp. 10103-10114
    • Peapus, D.H.1    Chiu, H.-J.2    Campobasso, N.3    Reddick, J.J.4    Begley, T.P.5    Ealick, S.E.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.