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Volumn 50, Issue 14, 2007, Pages 3359-3368

Structure-activity relationships of α-ketooxazole inhibitors of fatty acid amide hydrolase

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACID AMIDASE INHIBITOR; OL 135; UNCLASSIFIED DRUG;

EID: 34447538150     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061414r     Document Type: Article
Times cited : (72)

References (81)
  • 1
    • 2242490907 scopus 로고    scopus 로고
    • Structural Adaptations in a Membrane Enzyme That Terminates Endocannabinoid Signaling
    • Bracey, M. H.; Hanson, M. A.; Masuda, K. R.; Stevens, R. C.; Cravatt, B. F. Structural Adaptations in a Membrane Enzyme That Terminates Endocannabinoid Signaling. Science 2002, 298, 1793-1796.
    • (2002) Science , vol.298 , pp. 1793-1796
    • Bracey, M.H.1    Hanson, M.A.2    Masuda, K.R.3    Stevens, R.C.4    Cravatt, B.F.5
  • 2
    • 0029904838 scopus 로고    scopus 로고
    • Molecular Characterization of an Enzyme That Degrades Neuromodulatory Fatty Acid Amides
    • Cravatt, B. F.; Giang, D. K.; Mayfield, S. P.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. Molecular Characterization of an Enzyme That Degrades Neuromodulatory Fatty Acid Amides. Nature 1996, 384, 83-87.
    • (1996) Nature , vol.384 , pp. 83-87
    • Cravatt, B.F.1    Giang, D.K.2    Mayfield, S.P.3    Boger, D.L.4    Lerner, R.A.5    Gilula, N.B.6
  • 3
    • 0030903752 scopus 로고    scopus 로고
    • Molecular Characterization of Human and Mouse Fatty Acid Amide Hydrolases
    • Giang, D. K.; Cravatt, B. F. Molecular Characterization of Human and Mouse Fatty Acid Amide Hydrolases. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2238-2242.
    • (1997) Proc. Natl. Acad. Sci. U.S.A , vol.94 , pp. 2238-2242
    • Giang, D.K.1    Cravatt, B.F.2
  • 4
    • 0035235117 scopus 로고    scopus 로고
    • Proteins Regulating the Biosynthesis and Inactivation of Neuromodulatory Fatty Acid Amides
    • Patricelli, M. P.; Cravatt, B. F. Proteins Regulating the Biosynthesis and Inactivation of Neuromodulatory Fatty Acid Amides. Vitam. Horm. 2001, 62, 95-131.
    • (2001) Vitam. Horm , vol.62 , pp. 95-131
    • Patricelli, M.P.1    Cravatt, B.F.2
  • 5
    • 0038738350 scopus 로고    scopus 로고
    • Comparative Analysis of Fatty Acid Amide Hydrolase and CB1 Cannabinoid Receptor Expression in the Mouse Brain: Evidence of a Widespread Role for Fatty Acid Amide Hydrolase in Regulation of Endocannabinoid Signaling
    • Egertova, M.; Cravatt, B. F.; Elphick, M. R. Comparative Analysis of Fatty Acid Amide Hydrolase and CB1 Cannabinoid Receptor Expression in the Mouse Brain: Evidence of a Widespread Role for Fatty Acid Amide Hydrolase in Regulation of Endocannabinoid Signaling. Neuroscience 2003, 119, 481-496.
    • (2003) Neuroscience , vol.119 , pp. 481-496
    • Egertova, M.1    Cravatt, B.F.2    Elphick, M.R.3
  • 6
    • 0033607236 scopus 로고    scopus 로고
    • Fatty Acid Amide Hydrolase Competitively Degrades Bioactive Amides and Esters through a Nonconventional Catalytic Mechanism
    • Patricelli, M. P.; Cravatt, B. F. Fatty Acid Amide Hydrolase Competitively Degrades Bioactive Amides and Esters through a Nonconventional Catalytic Mechanism. Biochemistry 1999, 38, 14125-14130.
    • (1999) Biochemistry , vol.38 , pp. 14125-14130
    • Patricelli, M.P.1    Cravatt, B.F.2
  • 7
    • 0034705440 scopus 로고    scopus 로고
    • Clarifying the Catalytic Roles of Conserved Residues in the Amidase Signature Family
    • Patricelli, M. P.; Cravatt, B. F. Clarifying the Catalytic Roles of Conserved Residues in the Amidase Signature Family. J. Biol. Chem. 2000, 275, 19177-19184.
    • (2000) J. Biol. Chem , vol.275 , pp. 19177-19184
    • Patricelli, M.P.1    Cravatt, B.F.2
  • 8
    • 0033520099 scopus 로고    scopus 로고
    • Chemical and Mutagenic Investigations of Fatty Acid Amide Hydrolase: Evidence for a Family of Serine Hydrolases with Distinct Catalytic Properties
    • Patricelli, M. P.; Lovato, M. A.; Cravatt, B. F. Chemical and Mutagenic Investigations of Fatty Acid Amide Hydrolase: Evidence for a Family of Serine Hydrolases with Distinct Catalytic Properties. Biochemistry 1999, 38, 9804-9812.
    • (1999) Biochemistry , vol.38 , pp. 9804-9812
    • Patricelli, M.P.1    Lovato, M.A.2    Cravatt, B.F.3
  • 10
    • 0031716079 scopus 로고    scopus 로고
    • Boger, D. L.; Henriksen, S. J.; Cravatt, B. F. Oleamide: An Endogenous Sleep-Inducing Lipid and Prototypical Member of a New Class of Lipid Signalling Molecules. Curr. Pharm. Des. 1998, 4, 303-314.
    • Boger, D. L.; Henriksen, S. J.; Cravatt, B. F. Oleamide: An Endogenous Sleep-Inducing Lipid and Prototypical Member of a New Class of Lipid Signalling Molecules. Curr. Pharm. Des. 1998, 4, 303-314.
  • 11
    • 0030041883 scopus 로고    scopus 로고
    • Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide): A Synthetic Approach to the Chemical Analysis of Trace Quantitites of a Natural Product
    • Cravatt, B. F.; Lerner, R. A.; Boger, D. L. Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide): A Synthetic Approach to the Chemical Analysis of Trace Quantitites of a Natural Product. J. Am. Chem. Soc. 1996, 118, 580-590.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 580-590
    • Cravatt, B.F.1    Lerner, R.A.2    Boger, D.L.3
  • 15
    • 0025676296 scopus 로고
    • N-Acylated Glycerophospholipids and Their Derivatives
    • Schmid, H. H. O.; Schmid, P. C.; Natarajan, V. N-Acylated Glycerophospholipids and Their Derivatives. Prog. Lipid Res. 1990, 29, 1-43.
    • (1990) Prog. Lipid Res , vol.29 , pp. 1-43
    • Schmid, H.H.O.1    Schmid, P.C.2    Natarajan, V.3
  • 16
    • 23444432920 scopus 로고    scopus 로고
    • The Endocannabinoid System: Drug Targets, Lead Compounds, and Potential Therapeutic Applications
    • Lambert, D. M.; Fowler, C. J. The Endocannabinoid System: Drug Targets, Lead Compounds, and Potential Therapeutic Applications. J. Med. Chem. 2005, 48, 5059-5087.
    • (2005) J. Med. Chem , vol.48 , pp. 5059-5087
    • Lambert, D.M.1    Fowler, C.J.2
  • 17
    • 0032537734 scopus 로고    scopus 로고
    • Control of Pain Initiation by Endogenous Cannabinoids
    • Calignano, A.; La Rana, G.; Giuffrida, A.; Piomelli, D. Control of Pain Initiation by Endogenous Cannabinoids. Nature 1998, 394, 277-281.
    • (1998) Nature , vol.394 , pp. 277-281
    • Calignano, A.1    La Rana, G.2    Giuffrida, A.3    Piomelli, D.4
  • 18
    • 4644372326 scopus 로고    scopus 로고
    • The Endogenous Cannabinoid System and Its Role in Nociceptive Behavior
    • Cravatt, B. F.; Lichtman, A. H. The Endogenous Cannabinoid System and Its Role in Nociceptive Behavior. J. Neurobiol 2004, 61, 149-160.
    • (2004) J. Neurobiol , vol.61 , pp. 149-160
    • Cravatt, B.F.1    Lichtman, A.H.2
  • 21
    • 0036607403 scopus 로고    scopus 로고
    • Observational Analysis of Feeding Induced by δ-THC and Anandamide
    • Williams, C. M.; Kirkham, T. C. Observational Analysis of Feeding Induced by δ-THC and Anandamide. Physiol. Behav. 2002, 76, 241-250.
    • (2002) Physiol. Behav , vol.76 , pp. 241-250
    • Williams, C.M.1    Kirkham, T.C.2
  • 23
    • 0033405883 scopus 로고    scopus 로고
    • Involvement of the cAMP/Protein Kinase A Pathway and of Mitogen-Activated Protein Kinase in the Anti-proliferative Effects of Anandamide in Human Breast Cancer Cells
    • Melck, D.; Rueda, D.; Galve-Roberh, I.; De Petrocellis, L.; Guzmán, M.; Di Marzo, V. Involvement of the cAMP/Protein Kinase A Pathway and of Mitogen-Activated Protein Kinase in the Anti-proliferative Effects of Anandamide in Human Breast Cancer Cells. FEBS Lett. 1999, 463, 235-240.
    • (1999) FEBS Lett , vol.463 , pp. 235-240
    • Melck, D.1    Rueda, D.2    Galve-Roberh, I.3    De Petrocellis, L.4    Guzmán, M.5    Di Marzo, V.6
  • 26
    • 0031593783 scopus 로고    scopus 로고
    • The Cannabinoid CB1 Receptor Antagonist SR141716A Attenuates the Memory Impairment Produced by Δ9- Tetrahydrocannabinol or Anandamide
    • Mallet, P. E.; Beninger, R. J. The Cannabinoid CB1 Receptor Antagonist SR141716A Attenuates the Memory Impairment Produced by Δ9- Tetrahydrocannabinol or Anandamide. Psychopharmacology 1998, 140, 11-19.
    • (1998) Psychopharmacology , vol.140 , pp. 11-19
    • Mallet, P.E.1    Beninger, R.J.2
  • 28
    • 0031922630 scopus 로고    scopus 로고
    • Cannabinoid Receptors and Their Endogenous Agonist, Anandamide
    • Axelrod, J.; Felder, C. C. Cannabinoid Receptors and Their Endogenous Agonist, Anandamide. Neurochem. Res. 1998, 23, 575-581.
    • (1998) Neurochem. Res , vol.23 , pp. 575-581
    • Axelrod, J.1    Felder, C.C.2
  • 29
    • 0032784084 scopus 로고    scopus 로고
    • Cannabimimetic Fatty Acid Derivatives: The Anandamide Family and Other Endocannabinoids
    • Di Marzo, V.; Bisogno, T.; De Petrocellis, L.; Melck, D.; Martin, B. R. Cannabimimetic Fatty Acid Derivatives: The Anandamide Family and Other "Endocannabinoids." Curr. Med. Chem. 1999, 6, 721-744.
    • (1999) Curr. Med. Chem , vol.6 , pp. 721-744
    • Di Marzo, V.1    Bisogno, T.2    De Petrocellis, L.3    Melck, D.4    Martin, B.R.5
  • 30
    • 0033538561 scopus 로고    scopus 로고
    • Discovery and Characterization of Endogenous Cannabinoids
    • Martin, B. R.; Mechoulam, R.; Razdan, R. K. Discovery and Characterization of Endogenous Cannabinoids. Life Sci. 1999, 65, 573-595.
    • (1999) Life Sci , vol.65 , pp. 573-595
    • Martin, B.R.1    Mechoulam, R.2    Razdan, R.K.3
  • 31
    • 0032586854 scopus 로고    scopus 로고
    • Modification of 5-HT2 Receptor Mediated Behaviour in the Rat by Oleamide and the Role of Cannabinoid Receptors
    • Cheer, J. F.; Cadogan, A. K.; Marsden, C. A.; Fone, K. C. F.; Kendall, D. A. Modification of 5-HT2 Receptor Mediated Behaviour in the Rat by Oleamide and the Role of Cannabinoid Receptors. Neuropharmacology 1999, 38, 533-541.
    • (1999) Neuropharmacology , vol.38 , pp. 533-541
    • Cheer, J.F.1    Cadogan, A.K.2    Marsden, C.A.3    Fone, K.C.F.4    Kendall, D.A.5
  • 32
    • 0033013899 scopus 로고    scopus 로고
    • The Endogenous Lipid Oleamide Activates Serotonin 5-HT7 Neurons in Mouse Thalamus and Hypothalamus
    • Thomas, E. A.; Cravatt, B. F.; Sutcliffe, J. G. The Endogenous Lipid Oleamide Activates Serotonin 5-HT7 Neurons in Mouse Thalamus and Hypothalamus. J. Neurochem. 1999, 72, 2370-2378.
    • (1999) J. Neurochem , vol.72 , pp. 2370-2378
    • Thomas, E.A.1    Cravatt, B.F.2    Sutcliffe, J.G.3
  • 33
    • 0032516022 scopus 로고    scopus 로고
    • Structural Requirements for 5-HT2A and 5-HT1A Receptor Potentiation by the Biologically Active Lipid Oleamide
    • Boger, D. L.; Patterson, J. E.; Jin, Q. Structural Requirements for 5-HT2A and 5-HT1A Receptor Potentiation by the Biologically Active Lipid Oleamide. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4102-4107.
    • (1998) Proc. Natl. Acad. Sci. U.S.A , vol.95 , pp. 4102-4107
    • Boger, D.L.1    Patterson, J.E.2    Jin, Q.3
  • 34
    • 0346094445 scopus 로고    scopus 로고
    • Differential Effects of the Sleep-Inducing Lipid Oleamide and Cannabinoids on the Induction of Long-Term Potentiation in the CA1 Neurons of the Rat Hippocampus in Vitro
    • Lees, G.; Dougalis, A. Differential Effects of the Sleep-Inducing Lipid Oleamide and Cannabinoids on the Induction of Long-Term Potentiation in the CA1 Neurons of the Rat Hippocampus in Vitro. Brain Res. 2004, 997, 1-14.
    • (2004) Brain Res , vol.997 , pp. 1-14
    • Lees, G.1    Dougalis, A.2
  • 35
    • 0031811635 scopus 로고    scopus 로고
    • Oleamide Potentiates Benzodiazepine-Sensitive γ-Aminobutyric Acid Receptor Activity but Does Not Alter Minimum Alveolar Anesthetic Concentration
    • Yost, C. S.; Hampson, A. J.; Leonoudakis, D.; Koblin, D. D.; Bornheim, L. M.; Gray, A. T. Oleamide Potentiates Benzodiazepine-Sensitive γ-Aminobutyric Acid Receptor Activity but Does Not Alter Minimum Alveolar Anesthetic Concentration. Anesth. Analg. 1998, 86, 1294-1299.
    • (1998) Anesth. Analg , vol.86 , pp. 1294-1299
    • Yost, C.S.1    Hampson, A.J.2    Leonoudakis, D.3    Koblin, D.D.4    Bornheim, L.M.5    Gray, A.T.6
  • 36
    • 0035211628 scopus 로고    scopus 로고
    • Effect of Oleamide on Sleep and Its Relationship to Blood Pressure, Body Temperature, and Locomotor Activity in Rats
    • Huitrón-Reséndiz, S.; Gombart, L.; Cravatt, B. F.; Henriksen, S. J. Effect of Oleamide on Sleep and Its Relationship to Blood Pressure, Body Temperature, and Locomotor Activity in Rats. Exp. Neurol. 2001, 172, 235-243.
    • (2001) Exp. Neurol , vol.172 , pp. 235-243
    • Huitrón-Reséndiz, S.1    Gombart, L.2    Cravatt, B.F.3    Henriksen, S.J.4
  • 37
    • 0032574736 scopus 로고    scopus 로고
    • Chemical Requirements for Inhibition of Gap Junction Communication by the Biologically Active Lipid Oleamide
    • Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. F.; Lerner, R. A.; Gilula, N. B. Chemical Requirements for Inhibition of Gap Junction Communication by the Biologically Active Lipid Oleamide. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4810-4815.
    • (1998) Proc. Natl. Acad. Sci. U.S.A , vol.95 , pp. 4810-4815
    • Boger, D.L.1    Patterson, J.E.2    Guan, X.3    Cravatt, B.F.4    Lerner, R.A.5    Gilula, N.B.6
  • 38
    • 0031425481 scopus 로고    scopus 로고
    • The Sleep-Inducing Lipid Oleamide Deconvolutes Gap Junction Communication and Calcium Wave Transmission in Glial Cells
    • Guan, X.; Cravatt, B. F.; Ehring, G. R.; Hall, J. E.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. The Sleep-Inducing Lipid Oleamide Deconvolutes Gap Junction Communication and Calcium Wave Transmission in Glial Cells. J. Cell Biol. 1997, 139, 1785-1792.
    • (1997) J. Cell Biol , vol.139 , pp. 1785-1792
    • Guan, X.1    Cravatt, B.F.2    Ehring, G.R.3    Hall, J.E.4    Boger, D.L.5    Lerner, R.A.6    Gilula, N.B.7
  • 40
    • 0038545287 scopus 로고    scopus 로고
    • Increased Seizure Susceptibility and Proconvulsant Activity of Anandamide in Mice Lacking Fatty Acid Amide Hydrolase
    • Clement, A. B.; Hawkins, E. G.; Lichtman, A. H.; Cravatt, B. F. Increased Seizure Susceptibility and Proconvulsant Activity of Anandamide in Mice Lacking Fatty Acid Amide Hydrolase. J. Neurosci. 2003, 23, 3916-3923.
    • (2003) J. Neurosci , vol.23 , pp. 3916-3923
    • Clement, A.B.1    Hawkins, E.G.2    Lichtman, A.H.3    Cravatt, B.F.4
  • 43
    • 2442510225 scopus 로고    scopus 로고
    • Mice Lacking Fatty Acid Amide Hydrolase Exhibit a Cannabinoid Receptor-Mediated Phenotypic Hypoalgesia
    • Lichtman, A. H.; Shelton, C. C.; Advani, T.; Cravatt, B. F. Mice Lacking Fatty Acid Amide Hydrolase Exhibit a Cannabinoid Receptor-Mediated Phenotypic Hypoalgesia. Pain 2004, 109, 319-327.
    • (2004) Pain , vol.109 , pp. 319-327
    • Lichtman, A.H.1    Shelton, C.C.2    Advani, T.3    Cravatt, B.F.4
  • 44
    • 0042572380 scopus 로고    scopus 로고
    • Fatty Acid Amide Hydrolase: An Emerging Therapeutic Target in the Endocannabinoid System
    • Cravatt, B. F.; Lichtman, A. H. Fatty Acid Amide Hydrolase: An Emerging Therapeutic Target in the Endocannabinoid System. Curr. Opin. Chem. Biol. 2003, 7, 469-475.
    • (2003) Curr. Opin. Chem. Biol , vol.7 , pp. 469-475
    • Cravatt, B.F.1    Lichtman, A.H.2
  • 46
    • 0033579908 scopus 로고    scopus 로고
    • Trifluoromethyl Ketone Inhibitors of Fatty Acid Amide Hydrolase: A Probe of Structural and Conformational Features Contributing to Inhibition
    • Boger, D. L.; Sato, H.; Lerner, A. E.; Austin, B. J.; Patterson, J. E.; Patricelli, M. P.; Cravatt, B. F. Trifluoromethyl Ketone Inhibitors of Fatty Acid Amide Hydrolase: A Probe of Structural and Conformational Features Contributing to Inhibition. Bioorg. Med. Chem. Lett. 1999, 9, 265-270.
    • (1999) Bioorg. Med. Chem. Lett , vol.9 , pp. 265-270
    • Boger, D.L.1    Sato, H.2    Lerner, A.E.3    Austin, B.J.4    Patterson, J.E.5    Patricelli, M.P.6    Cravatt, B.F.7
  • 51
    • 9644270298 scopus 로고    scopus 로고
    • Heterocyclic Sulfoxide and Sulfone Inhibitors of Fatty Acid Amide Hydrolase
    • Du, W.; Hardouin, C.; Cheng, H.; Hwang, I.; Boger, D. L. Heterocyclic Sulfoxide and Sulfone Inhibitors of Fatty Acid Amide Hydrolase. Bioorg. Med. Chem. Lett. 2005, 15, 103-106.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 103-106
    • Du, W.1    Hardouin, C.2    Cheng, H.3    Hwang, I.4    Boger, D.L.5
  • 52
    • 0031847458 scopus 로고    scopus 로고
    • Edgemond, W. S.; Greenberg, M. J.; McGinley, P. J.; Muthians, S.; Campbell, W. B.; Hillard, C. J. Synthesis and Characterization of Diazomethylarachidonyl Ketone: An Irreversible Inhibitor of N- Arachidonylethanolamine Amidohydrolase. J. Pharmacol. Exp. Ther. 1998, 286, 184-190.
    • Edgemond, W. S.; Greenberg, M. J.; McGinley, P. J.; Muthians, S.; Campbell, W. B.; Hillard, C. J. Synthesis and Characterization of Diazomethylarachidonyl Ketone: An Irreversible Inhibitor of N- Arachidonylethanolamine Amidohydrolase. J. Pharmacol. Exp. Ther. 1998, 286, 184-190.
  • 53
    • 0030759362 scopus 로고    scopus 로고
    • Evidence That Methyl Arachidonyl Fluorophosphonate Is an Irreversible Cannabinoid Receptor Antagonist
    • Fernando, S. R.; Pertwee, R. G. Evidence That Methyl Arachidonyl Fluorophosphonate Is an Irreversible Cannabinoid Receptor Antagonist. Br. J. Pharmacol. 1997, 121, 1716-1720.
    • (1997) Br. J. Pharmacol , vol.121 , pp. 1716-1720
    • Fernando, S.R.1    Pertwee, R.G.2
  • 55
    • 0032539873 scopus 로고    scopus 로고
    • An Endogenous Sleep-Inducing Compound Is a Novel Competitive Inhibitor of Fatty Acid Amide Hydrolase
    • Patricelli, M. P.; Patterson, J. P.; Boger, D. L.; Cravatt, B. F. An Endogenous Sleep-Inducing Compound Is a Novel Competitive Inhibitor of Fatty Acid Amide Hydrolase. Bioorg. Med. Chem. Lett. 1998, 8, 613-618.
    • (1998) Bioorg. Med. Chem. Lett , vol.8 , pp. 613-618
    • Patricelli, M.P.1    Patterson, J.P.2    Boger, D.L.3    Cravatt, B.F.4
  • 56
    • 0030037917 scopus 로고    scopus 로고
    • Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid cis-9-Octadecenamide
    • Patterson, J. E.; Ollmann, I. R.; Cravatt, B. F.; Boger, D. L.; Wong, C.-H.; Lerner, R. A. Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid cis-9-Octadecenamide. J. Am. Chem. Soc. 1996, 1996, 5938-5945.
    • (1996) J. Am. Chem. Soc , vol.1996 , pp. 5938-5945
    • Patterson, J.E.1    Ollmann, I.R.2    Cravatt, B.F.3    Boger, D.L.4    Wong, C.-H.5    Lerner, R.A.6
  • 57
    • 33746301093 scopus 로고    scopus 로고
    • Synthesis and Structure-Activity Relationships of FAAH Inhibitors: Cyclohexylcarbamic Acid Biphenyl Esters with Chemical Modulation at the Proximal Phenyl Ring
    • Tarzia, G.; Duranti, A.; Gatti, G.; Piersanti, G.; Tontini, A.; Rivara, S.; Lodola, A.; Plazzi, P. V.; Mor, M.; Kathuria, S.; Piomelli, D. Synthesis and Structure-Activity Relationships of FAAH Inhibitors: Cyclohexylcarbamic Acid Biphenyl Esters with Chemical Modulation at the Proximal Phenyl Ring. ChemMedChem 2006, 1, 130-139.
    • (2006) ChemMedChem , vol.1 , pp. 130-139
    • Tarzia, G.1    Duranti, A.2    Gatti, G.3    Piersanti, G.4    Tontini, A.5    Rivara, S.6    Lodola, A.7    Plazzi, P.V.8    Mor, M.9    Kathuria, S.10    Piomelli, D.11
  • 58
    • 12444260741 scopus 로고    scopus 로고
    • Tarzia, G.; Duranti, A.; Tontini, A.; Piersanti, G.; Mor, M.; Rivara, S.; Plazzi, P. V.; Park, C.; Kathuria, S.; Piomelli, D. Design, Synthesis, and Structure-Activity Relationships of Alkylcarbamic Acid Aryl Esters, a New Class of Fatty Acid Amide Hydrolase Inhibitors. J. Med. Chem. 2003, 46, 2352-2360.
    • Tarzia, G.; Duranti, A.; Tontini, A.; Piersanti, G.; Mor, M.; Rivara, S.; Plazzi, P. V.; Park, C.; Kathuria, S.; Piomelli, D. Design, Synthesis, and Structure-Activity Relationships of Alkylcarbamic Acid Aryl Esters, a New Class of Fatty Acid Amide Hydrolase Inhibitors. J. Med. Chem. 2003, 46, 2352-2360.
  • 59
    • 4744354729 scopus 로고    scopus 로고
    • Cyclohexylcarbamic Acid 3′- or 4′-Substituted Biphenyl-3-yl Esters as Fatty Acid Amide Hydrolase Inhibitors: Synthesis, Quantitative Structure-Activity Relationships, and Molecular Modeling Studies
    • Mor, M.; Rivara, S.; Lodola, A.; Plazzi, P. V.; Tarzia, G.; Duranti, A.; Tontini, A.; Piersanti, G.; Kathuria, S.; Piomelli, D. Cyclohexylcarbamic Acid 3′- or 4′-Substituted Biphenyl-3-yl Esters as Fatty Acid Amide Hydrolase Inhibitors: Synthesis, Quantitative Structure-Activity Relationships, and Molecular Modeling Studies. J. Med. Chem. 2004, 47, 4998-5008.
    • (2004) J. Med. Chem , vol.47 , pp. 4998-5008
    • Mor, M.1    Rivara, S.2    Lodola, A.3    Plazzi, P.V.4    Tarzia, G.5    Duranti, A.6    Tontini, A.7    Piersanti, G.8    Kathuria, S.9    Piomelli, D.10
  • 60
    • 30444452978 scopus 로고    scopus 로고
    • Substituted 2-Thioxoimidazolidin-4- ones and Imidazolidine-2,4-diones as Fatty Acid Amide Hydrolase Inhibitors Templates
    • Muccioli, G. G.; Fazio, N.; Scriba, G. K. E.; Poppitz, W.; Cannata, F.; Poupaert, J. H.; Wouters, J.; Lambert, D. M. Substituted 2-Thioxoimidazolidin-4- ones and Imidazolidine-2,4-diones as Fatty Acid Amide Hydrolase Inhibitors Templates. J. Med. Chem. 2006, 49, 417-425.
    • (2006) J. Med. Chem , vol.49 , pp. 417-425
    • Muccioli, G.G.1    Fazio, N.2    Scriba, G.K.E.3    Poppitz, W.4    Cannata, F.5    Poupaert, J.H.6    Wouters, J.7    Lambert, D.M.8
  • 61
    • 13944263535 scopus 로고    scopus 로고
    • Discovery of an Exceptionally Potent and Selective Class of Fatty Acid Amide Hydrolase Inhibitors Enlisting Proteome-Wide Selectivity Screening: Concurrent Optimization of Enzyme Inhibitor Potency and Selectivity
    • Leung, D.; Du, W.; Hardouin, C.; Cheng, H.; Hwang, I.; Cravatt, B. F.; Boger, D. L. Discovery of an Exceptionally Potent and Selective Class of Fatty Acid Amide Hydrolase Inhibitors Enlisting Proteome-Wide Selectivity Screening: Concurrent Optimization of Enzyme Inhibitor Potency and Selectivity. Bioorg. Med. Chem. Lett. 2005, 15, 1423-1428.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 1423-1428
    • Leung, D.1    Du, W.2    Hardouin, C.3    Cheng, H.4    Hwang, I.5    Cravatt, B.F.6    Boger, D.L.7
  • 63
    • 27744466783 scopus 로고    scopus 로고
    • Mechanism of Carbamate Inactivation of FAAH: Implications for the Design of Covalent Inhibitors and in Vivo Functional Probes for Enzymes
    • Alexander, J. P.; Cravatt, B. F. Mechanism of Carbamate Inactivation of FAAH: Implications for the Design of Covalent Inhibitors and in Vivo Functional Probes for Enzymes. Chem. Biol. 2005, 12, 1179-1187.
    • (2005) Chem. Biol , vol.12 , pp. 1179-1187
    • Alexander, J.P.1    Cravatt, B.F.2
  • 64
    • 4644354869 scopus 로고    scopus 로고
    • Reversible Inhibitors of Fatty Acid Amide Hydrolase That Promote Analgesia: Evidence for an Unprecedented Combination of Potency and Selectivity
    • Lichtman, A. H.; Leung, D.; Shelton, C. C.; Saghatelian, A.; Hardouin, C.; Boger, D. L.; Cravatt, B. F. Reversible Inhibitors of Fatty Acid Amide Hydrolase That Promote Analgesia: Evidence for an Unprecedented Combination of Potency and Selectivity. J. Pharmacol. Exp. Ther. 2004, 311, 441-448.
    • (2004) J. Pharmacol. Exp. Ther , vol.311 , pp. 441-448
    • Lichtman, A.H.1    Leung, D.2    Shelton, C.C.3    Saghatelian, A.4    Hardouin, C.5    Boger, D.L.6    Cravatt, B.F.7
  • 66
    • 33746605204 scopus 로고    scopus 로고
    • The Putative Endocannabinoid Transport Blocker LY2183240 Is a Potent Inhibitor of FAAH and Several Other Brain Serine Hydrolases
    • Alexander, J. P.; Cravatt, B. F. The Putative Endocannabinoid Transport Blocker LY2183240 Is a Potent Inhibitor of FAAH and Several Other Brain Serine Hydrolases. J. Am. Chem. Soc. 2006, 128, 9699-9704.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 9699-9704
    • Alexander, J.P.1    Cravatt, B.F.2
  • 67
    • 0035907462 scopus 로고    scopus 로고
    • α-Keto Heterocycle Inhibitors of Fatty Acid Amide Hydrolase: Carbonyl Group Modification and α-Substitution
    • Boger, D. L.; Miyauchi, H.; Hedrick, M. P. α-Keto Heterocycle Inhibitors of Fatty Acid Amide Hydrolase: Carbonyl Group Modification and α-Substitution. Bioorg. Med. Chem. Lett. 2001, 11, 1517-1520.
    • (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 1517-1520
    • Boger, D.L.1    Miyauchi, H.2    Hedrick, M.P.3
  • 69
    • 33750487830 scopus 로고    scopus 로고
    • Delineation of a Fundamental α-Ketoheterocycle Substituent Effect for Use in the Design of Enzyme Inhibitors
    • Romero, F. A.; Hwang, I.; Boger, D. L. Delineation of a Fundamental α-Ketoheterocycle Substituent Effect for Use in the Design of Enzyme Inhibitors. J. Am. Chem. Soc. 2006, 68, 14004-14005.
    • (2006) J. Am. Chem. Soc , vol.68 , pp. 14004-14005
    • Romero, F.A.1    Hwang, I.2    Boger, D.L.3
  • 70
    • 33847783305 scopus 로고    scopus 로고
    • Potent and Selective α-Ketoheterocycle-Based Inhibitors of the Anandamide and Oleamide Catabolizing Enzyme, Fatty Acid Amide Hydrolase
    • Romero, F. A.; Du, W.; Hwang, I.; Rayl, T. J.; Leung, D.; Hoover, H. S.; Cravatt, B. F.; Boger, D. L. Potent and Selective α-Ketoheterocycle-Based Inhibitors of the Anandamide and Oleamide Catabolizing Enzyme, Fatty Acid Amide Hydrolase. J. Med. Chem. 2007, 50, 1058-1068.
    • (2007) J. Med. Chem , vol.50 , pp. 1058-1068
    • Romero, F.A.1    Du, W.2    Hwang, I.3    Rayl, T.J.4    Leung, D.5    Hoover, H.S.6    Cravatt, B.F.7    Boger, D.L.8
  • 71
    • 0038361307 scopus 로고    scopus 로고
    • Discovering Potent and Selective Reversible Inhibitors of Enzymes in Complex Proteomes
    • Leung, D.; Hardouin, C.; Boger, D. L.; Cravatt, B. F. Discovering Potent and Selective Reversible Inhibitors of Enzymes in Complex Proteomes. Nat. Biotechnol. 2003, 21, 687-691.
    • (2003) Nat. Biotechnol , vol.21 , pp. 687-691
    • Leung, D.1    Hardouin, C.2    Boger, D.L.3    Cravatt, B.F.4
  • 72
    • 9644285669 scopus 로고    scopus 로고
    • Sonogashira, K.; Tohda, Y.; Hagihara, N. A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines. Tetrahedron Lett. 1975, 16, 4467-4470.
    • Sonogashira, K.; Tohda, Y.; Hagihara, N. A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines. Tetrahedron Lett. 1975, 16, 4467-4470.
  • 73
    • 0018419770 scopus 로고
    • Synthesis of Furan Derivatives. LXXXV. Condensation of Heteroaromatic Aldehydes with Tosylmethyl Isocyanide
    • Saikachi, H.; Kitagawa, T.; Sasaki, H.; Van Leusen, A. M. Synthesis of Furan Derivatives. LXXXV. Condensation of Heteroaromatic Aldehydes with Tosylmethyl Isocyanide. Chem. Pharm. Bull. 1969, 27, 793-796.
    • (1969) Chem. Pharm. Bull , vol.27 , pp. 793-796
    • Saikachi, H.1    Kitagawa, T.2    Sasaki, H.3    Van Leusen, A.M.4
  • 74
    • 0029564227 scopus 로고
    • Acylation of Oxazoles by the Copper-Mediated Reaction of Oxazol-2-ylzinc Chloride Derivatives
    • Harn, N. K.; Gramer, C. J.; Anderson, B. A. Acylation of Oxazoles by the Copper-Mediated Reaction of Oxazol-2-ylzinc Chloride Derivatives. Tetrahedron Lett. 1995, 36, 9453-9456.
    • (1995) Tetrahedron Lett , vol.36 , pp. 9453-9456
    • Harn, N.K.1    Gramer, C.J.2    Anderson, B.A.3
  • 75
    • 0000659999 scopus 로고
    • Synthesis of (Trimethylsily 1)thiazoles and Reactions with Carbonyl Compounds. Selectivity Aspects and Synthetic Utility
    • Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Synthesis of (Trimethylsily 1)thiazoles and Reactions with Carbonyl Compounds. Selectivity Aspects and Synthetic Utility. J. Org. Chem. 1988, 53, 1748-1761.
    • (1988) J. Org. Chem , vol.53 , pp. 1748-1761
    • Dondoni, A.1    Fantin, G.2    Fogagnolo, M.3    Medici, A.4    Pedrini, P.5
  • 76
    • 84986477802 scopus 로고
    • Synthesis of Stannylthiazoles and Mixed Stannylsilylthiazoles and Their Use for a Convenient Preparation of Mono- and Bis-Halothiazoles
    • Dondoni, A.; Mastellari, A. R.; Medici, A.; Negrini, E.; Pedrini, P. Synthesis of Stannylthiazoles and Mixed Stannylsilylthiazoles and Their Use for a Convenient Preparation of Mono- and Bis-Halothiazoles. Synthesis 1986, 757-760.
    • (1986) Synthesis , pp. 757-760
    • Dondoni, A.1    Mastellari, A.R.2    Medici, A.3    Negrini, E.4    Pedrini, P.5
  • 77
    • 0348086869 scopus 로고
    • Enamines from Cyclopropylketones
    • Pocar, D.; Stradi, R.; Trimarco, P. Enamines from Cyclopropylketones. Tetrahedron 1975, 31, 2427-2429.
    • (1975) Tetrahedron , vol.31 , pp. 2427-2429
    • Pocar, D.1    Stradi, R.2    Trimarco, P.3
  • 78
    • 0039642317 scopus 로고
    • Acid-Catalyzed Addition of Secondary Amines to Cyclopropyl Ketones. Mass Spectra of Some Cyclic Aminobutyrophenones
    • Yovell, J.; Hirsch, D.; Sarel, S. Acid-Catalyzed Addition of Secondary Amines to Cyclopropyl Ketones. Mass Spectra of Some Cyclic Aminobutyrophenones. J. Org. Chem. 1977, 42, 850-855.
    • (1977) J. Org. Chem , vol.42 , pp. 850-855
    • Yovell, J.1    Hirsch, D.2    Sarel, S.3
  • 79
    • 0000352038 scopus 로고
    • Synthesis of α-Hydroxy Carbonyl Compounds (Acyloins): Direct Oxidation of Enolates Using 2-Sulfonyloxaziridines
    • Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. Synthesis of α-Hydroxy Carbonyl Compounds (Acyloins): Direct Oxidation of Enolates Using 2-Sulfonyloxaziridines. J. Org. Chem. 1984, 49, 3241-3243.
    • (1984) J. Org. Chem , vol.49 , pp. 3241-3243
    • Davis, F.A.1    Vishwakarma, L.C.2    Billmers, J.M.3    Finn, J.4
  • 80
    • 0032573124 scopus 로고    scopus 로고
    • Comparative Characterization of a Wild Type and Transmembrane Domain-Deleted Fatty Acid Amide Hydrolase: Identification of the Transmembrane Domain as a Site for Oligomerization
    • Patricelli, M. P.; Lashuel, H. A.; Giang, D. K.; Kelly, J. W.; Cravatt, B. F. Comparative Characterization of a Wild Type and Transmembrane Domain-Deleted Fatty Acid Amide Hydrolase: Identification of the Transmembrane Domain as a Site for Oligomerization. Biochemistry 1998, 37, 15177-15187.
    • (1998) Biochemistry , vol.37 , pp. 15177-15187
    • Patricelli, M.P.1    Lashuel, H.A.2    Giang, D.K.3    Kelly, J.W.4    Cravatt, B.F.5
  • 81
    • 34447569016 scopus 로고    scopus 로고
    • For 2b, MW = 334, four H-bond acceptors, and c log P = 4.11. For 5hh, MW = 369, four H-bond acceptors, and c log P = 4.61. For 11j, MW = 354, four H-bond acceptors, c log P = 4.12, and five rotatable bonds.
    • For 2b, MW = 334, four H-bond acceptors, and c log P = 4.11. For 5hh, MW = 369, four H-bond acceptors, and c log P = 4.61. For 11j, MW = 354, four H-bond acceptors, c log P = 4.12, and five rotatable bonds.


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