메뉴 건너뛰기




Volumn 51, Issue 15, 2008, Pages 4392-4403

Optimization of the central heterocycle of α-ketoheterocycle inhibitors of fatty acid amide hydrolase

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIAZINE DERIVATIVE; 1,2,4 OXADIAZOLE DERIVATIVE; 1,3,4 OXADIAZOLE DERIVATIVE; 1,3,4 THIADIAZOLE DERIVATIVE; FATTY ACID AMIDASE INHIBITOR; GABAPENTIN; IBUPROFEN; MORPHINE; OXAZOLE DERIVATIVE; TETRAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 49449114646     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800136b     Document Type: Article
Times cited : (87)

References (98)
  • 1
    • 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
  • 2
    • 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
  • 3
    • 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. Vit. Hormones 2001, 62, 95-131.
    • (2001) Vit. Hormones , vol.62 , pp. 95-131
    • Patricelli, M.P.1    Cravatt, B.F.2
  • 4
    • 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
  • 8
    • 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
  • 9
    • 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
  • 10
    • 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
  • 11
    • 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 Signaling 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 Signaling Molecules. Curr. Pharm. Des. 1998, 4, 303-314.
  • 12
    • 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
  • 14
    • 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
  • 15
    • 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
  • 16
    • 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
  • 17
    • 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
  • 18
    • 0035452256 scopus 로고    scopus 로고
    • Fatty Acid Amide Hydrolase: Biochemistry, Pharmacology, and Therapeutic Possibilities for an Enzyme Hydrolyzing Anandamide, 2-Arachidonoylglycerol, Palmitoylethanolamide, and Oleamide
    • Fowler, C. J.; Jonsson, K.-D.; Tiger, G. Fatty Acid Amide Hydrolase: Biochemistry, Pharmacology, and Therapeutic Possibilities for an Enzyme Hydrolyzing Anandamide, 2-Arachidonoylglycerol, Palmitoylethanolamide, and Oleamide. Biochem. Pharmacol. 2001, 62, 517-526.
    • (2001) Biochem. Pharmacol , vol.62 , pp. 517-526
    • Fowler, C.J.1    Jonsson, K.-D.2    Tiger, G.3
  • 19
    • 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
  • 20
    • 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
  • 22
    • 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
  • 25
    • 0035211628 scopus 로고    scopus 로고
    • Effect of Oleamide on Sleep and Its Relationship to Blood Pressure, Body Temperature, and Locomotor Activity in Rats
    • (a) 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
  • 26
    • 4143074761 scopus 로고    scopus 로고
    • Characterization of the Sleep-Wake Patterns in Mice Lacking Fatty Acid Amide Hydrolase
    • (b) Huitrón-Reséndiz, S.; Sanchez-Alavez, M.; Wills, D. N.; Cravatt, B. F.; Henriksen, S. J. Characterization of the Sleep-Wake Patterns in Mice Lacking Fatty Acid Amide Hydrolase. Sleep 2004, 27, 857-865.
    • (2004) Sleep , vol.27 , pp. 857-865
    • Huitrón-Reséndiz, S.1    Sanchez-Alavez, M.2    Wills, D.N.3    Cravatt, B.F.4    Henriksen, S.J.5
  • 27
    • 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
  • 28
    • 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
  • 30
    • 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, 118, 5938-5945.
    • (1996) J. Am. Chem. Soc , vol.118 , 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
  • 31
    • 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
  • 32
    • 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
  • 36
    • 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.
  • 37
    • 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
  • 38
    • 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
  • 42
    • 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
  • 43
    • 12444260741 scopus 로고    scopus 로고
    • Synthesis, and Structure - Activity Relationships of Alkylcarbamic Acid Aryl Esters, a New Class of Fatty Acid Amide Hydrolase Inhibitors
    • (a) 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.
    • (2003) J. Med. Chem , vol.46 , pp. 2352-2360
    • Tarzia, G.1    Duranti, A.2    Tontini, A.3    Piersanti, G.4    Mor, M.5    Rivara, S.6    Plazzi, P.V.7    Park, C.8    Kathuria, S.9    Piomelli10    Design, D.11
  • 44
    • 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
    • (b) 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. Chem. Med. Chem. 2006, 1, 130-139.
    • (2006) Chem. Med. Chem , 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
  • 46
    • 49449117132 scopus 로고    scopus 로고
    • Abouab-Dellah, A, Burnier, P, Hoornaert, C, Jeunesse, J, Puech, F, Sanofi, Derivatives of Piperidinyl-and Piperazinyl-alkyl Carbamates, Preparation Methods and Application in Therapeutics. Patent WO 2004/099176, 2004
    • (a) Abouab-Dellah, A.; Burnier, P.; Hoornaert, C.; Jeunesse, J.; Puech, F. (Sanofi). Derivatives of Piperidinyl-and Piperazinyl-alkyl Carbamates, Preparation Methods and Application in Therapeutics. Patent WO 2004/099176, 2004.
  • 47
    • 49449091784 scopus 로고    scopus 로고
    • Abouab-Dellah, A, Almario, G. A, Froissant, J, Hoornaert, C, Sanofi, Aryloxyalkylcarbamate Derivatives, Including Piperidine Carbamates, Their Preparation and Use as Fatty Acid Amide Hydrolase (FAAH) Inhibitors for Treating FAAH-Related Pathologies. Patent WO 2005/077898, 2005
    • (b) Abouab-Dellah, A.; Almario, G. A.; Froissant, J.; Hoornaert, C. (Sanofi). Aryloxyalkylcarbamate Derivatives, Including Piperidine Carbamates, Their Preparation and Use as Fatty Acid Amide Hydrolase (FAAH) Inhibitors for Treating FAAH-Related Pathologies. Patent WO 2005/077898, 2005.
  • 48
    • 49449095440 scopus 로고    scopus 로고
    • Abouab-Dellah, A, Almario, G. A, Hoornaert, C, Li, A. T, Sanofi, 1-Piperazine and 1-Homopiperazine Derivatives, Their Preparation and Use as Fatty Acid Amide Hydrolase (FAAH) Inhibitors for Treating FAAH-Related Pathologies. Patent WO 2005/070910, 2005
    • (c) Abouab-Dellah, A.; Almario, G. A.; Hoornaert, C.; Li, A. T. (Sanofi). 1-Piperazine and 1-Homopiperazine Derivatives, Their Preparation and Use as Fatty Acid Amide Hydrolase (FAAH) Inhibitors for Treating FAAH-Related Pathologies. Patent WO 2005/070910, 2005.
  • 49
    • 49449098754 scopus 로고    scopus 로고
    • Abouab-Dellah, A, Almario, G. A, Hoornaert, C, Li, A. T, Sanofi, Alkyl(homo)piperazine-carboxylate Derivatives, Their Preparation and Use as Fatty Acid Amide Hydrolase (FAAH) Inhibitors for Treating FAAH-Related Pathologies. Patent WO 2007/027141, 2007
    • (d) Abouab-Dellah, A.; Almario, G. A.; Hoornaert, C.; Li, A. T. (Sanofi). Alkyl(homo)piperazine-carboxylate Derivatives, Their Preparation and Use as Fatty Acid Amide Hydrolase (FAAH) Inhibitors for Treating FAAH-Related Pathologies. Patent WO 2007/027141, 2007.
  • 50
    • 49449106637 scopus 로고    scopus 로고
    • Sit, S.-Y, Xie, K, Deng, H, Bristol-Myers Squibb, Preparation of (Hetero)aryl Carbamates and Oximes as Fatty Acid Amide Hydrolase Inhibitors. Patent WO2003/06589, 2003
    • (a) Sit, S.-Y.; Xie, K.; Deng, H. (Bristol-Myers Squibb). Preparation of (Hetero)aryl Carbamates and Oximes as Fatty Acid Amide Hydrolase Inhibitors. Patent WO2003/06589, 2003.
  • 51
    • 49449087233 scopus 로고    scopus 로고
    • Sit, S.-Y, Xie, K, Bristol-Myers Squibb, Preparation of Bis Arylimidazolyl Fatty Acid Amide Hydrolase Inhibitors for Treatment of Pain. Patent WO 2002/0875692002
    • (b) Sit, S.-Y.; Xie, K. (Bristol-Myers Squibb). Preparation of Bis Arylimidazolyl Fatty Acid Amide Hydrolase Inhibitors for Treatment of Pain. Patent WO 2002/0875692002.
  • 53
    • 49449115225 scopus 로고    scopus 로고
    • Apodaca, R, Breitenbucher, J. G, Pattabiraman, K, Seierstad, M, Xiao, W, J&J, Piperazinvl and Piperidinyl Ureas as Modulators of Fatty Acid Amide Hydrolase. U.S. Patent 2006/01731842006
    • (a) Apodaca, R.; Breitenbucher, J. G.; Pattabiraman, K.; Seierstad, M.; Xiao, W. (J&J). Piperazinvl and Piperidinyl Ureas as Modulators of Fatty Acid Amide Hydrolase. U.S. Patent 2006/01731842006.
  • 54
    • 49449106814 scopus 로고    scopus 로고
    • Apodaca, R, Breitenbucher, J. G, Pattabiraman, K, Seierstad, M, Xiao, W, J&J, Preparation of Thiadiazolylpiperazine Carboxamides as Modulators of Fatty Acid Amide Hydrolase FAAH, U.S. Patent 2007/0047412007
    • (b) Apodaca, R.; Breitenbucher, J. G.; Pattabiraman, K.; Seierstad, M.; Xiao, W. (J&J). Preparation of Thiadiazolylpiperazine Carboxamides as Modulators of Fatty Acid Amide Hydrolase (FAAH). U.S. Patent 2007/0047412007.
  • 55
    • 49449108174 scopus 로고    scopus 로고
    • Matsumoto, T, Kori, M, Miyazaki, J, Kiyota, Y, Takeda, Preparation of Piperidinecarboxamides and Piperazinecarboxamides as Fatty Acid Amide Hydrolase (FAAH) Inhibitors. Patent WO 2006054652, 2006
    • (a) Matsumoto, T.; Kori, M.; Miyazaki, J.; Kiyota, Y. (Takeda). Preparation of Piperidinecarboxamides and Piperazinecarboxamides as Fatty Acid Amide Hydrolase (FAAH) Inhibitors. Patent WO 2006054652, 2006.
  • 56
    • 49449093690 scopus 로고    scopus 로고
    • Matsumoto, T, Kori, M, Kouno, M, Takeda, Preparation of Piperazine-1-carboxamide Derivatives as Brain/Neuronal Cell-protecting Agents, and Therapeutic Agents for Sleep Disorder. Patent WO 2007020888, 2007
    • (b) Matsumoto, T.; Kori, M.; Kouno, M. (Takeda). Preparation of Piperazine-1-carboxamide Derivatives as Brain/Neuronal Cell-protecting Agents, and Therapeutic Agents for Sleep Disorder. Patent WO 2007020888, 2007.
  • 57
    • 49449107646 scopus 로고    scopus 로고
    • Ishii, T, Sugane, T, Maeda, J, Narazaki, F, Kakefuda, A, Sato, K, Takahashi, T, Kanayama, T, Saitoh, C, Suzuki, J, Kanai, C, Astellas, Preparation of Pyridyl Nonaromatic Nitrogenated Heterocyclic-1-carboxylate Ester Derivatives as FAAH Inhibitors, Patent WO 2006/088075, 2006
    • Ishii, T.; Sugane, T.; Maeda, J.; Narazaki, F.; Kakefuda, A.; Sato, K.; Takahashi, T.; Kanayama, T.; Saitoh, C.; Suzuki, J.; Kanai, C. (Astellas). Preparation of Pyridyl Nonaromatic Nitrogenated Heterocyclic-1-carboxylate Ester Derivatives as FAAH Inhibitors, Patent WO 2006/088075, 2006.
  • 59
    • 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
  • 60
    • 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
  • 63
    • 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
  • 65
    • 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
  • 66
    • 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
    • 4644354869 scopus 로고    scopus 로고
    • Reversible Inhibitors of Fatty Acid Amide Hydrolase that Promote Analgesia: Evidence for an Unprecedented Combination of Potency and Selectivity
    • (a) 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
  • 72
    • 30444452978 scopus 로고    scopus 로고
    • Substituted 2-Thioxoimidazolidin-4-ones and Imidazolidine-2,4-diones as Fatty Acid Amide Hydrolase Inhibitors Templates
    • (a) 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
  • 73
    • 33746718652 scopus 로고    scopus 로고
    • Fatty Acid Amide Hydrolase Inhibitors from Virtual Screening of the Endocannabinoid System
    • (b) Saario, S. M.; Poso, A.; Juvonen, R. O.; Jarvinen, T.; Salo-Ahen, O. M. H. Fatty Acid Amide Hydrolase Inhibitors from Virtual Screening of the Endocannabinoid System. J. Med. Chem. 2006, 49, 4650-4656.
    • (2006) J. Med. Chem , vol.49 , pp. 4650-4656
    • Saario, S.M.1    Poso, A.2    Juvonen, R.O.3    Jarvinen, T.4    Salo-Ahen, O.M.H.5
  • 74
    • 34548131105 scopus 로고    scopus 로고
    • Design, Synthesis, and In Vitro Evaluation of Carbamate Derivatives of 2-Benzoxazolyl- and 2-Benzothiazolyl-(3-hydroxyphenyl)-methanones as Novel Fatty Acid Amide Hydrolase Inhibitors
    • (c) Myllymaki, M. J.; Saario, S. M.; Kataja, A. O.; Castillo-Melendez, J. A.; Navalainen, T.; Juvonen, R. O.; Jarvinen, T.; Koskinen, A. M. P. Design, Synthesis, and In Vitro Evaluation of Carbamate Derivatives of 2-Benzoxazolyl- and 2-Benzothiazolyl-(3-hydroxyphenyl)-methanones as Novel Fatty Acid Amide Hydrolase Inhibitors. J. Med. Chem. 2007, 50, 4236-4242.
    • (2007) J. Med. Chem , vol.50 , pp. 4236-4242
    • Myllymaki, M.J.1    Saario, S.M.2    Kataja, A.O.3    Castillo-Melendez, J.A.4    Navalainen, T.5    Juvonen, R.O.6    Jarvinen, T.7    Koskinen, A.M.P.8
  • 75
    • 0000119823 scopus 로고
    • A Convenient Synthesis of t-Butyldimethylsilyl Protected Cyanohydrins
    • Rawal, V. H.; Rao, J. A.; Cava, M. P. A Convenient Synthesis of t-Butyldimethylsilyl Protected Cyanohydrins. Tetrahedron Lett. 1985, 26, 4275-4278.
    • (1985) Tetrahedron Lett , vol.26 , pp. 4275-4278
    • Rawal, V.H.1    Rao, J.A.2    Cava, M.P.3
  • 76
    • 49449107066 scopus 로고
    • Reactions of Sodium Hydrazide with Organic Compounds
    • (a) Kauffman, Th. Reactions of Sodium Hydrazide with Organic Compounds. Angew. Chem., Int. Ed. 1964, 3, 342-353.
    • (1964) Angew. Chem., Int. Ed , vol.3 , pp. 342-353
    • Kauffman, T.1
  • 77
    • 14644418486 scopus 로고    scopus 로고
    • Garg, N. K.; Stoltz, B. M. Synthesis of Bis(indole)-1,2,4- triazinones. Tetrahedron Lett. 2005, 46, 1997-2000.
    • (b) Garg, N. K.; Stoltz, B. M. Synthesis of Bis(indole)-1,2,4- triazinones. Tetrahedron Lett. 2005, 46, 1997-2000.
  • 78
    • 33751386451 scopus 로고
    • Pyrrole as a Dienophile in Intramolecular Inverse Electron-Demand Diels - Alder Reactions with 1,2,4-Triazines
    • (c) Li, J. H.; Snyder, J. K. Pyrrole as a Dienophile in Intramolecular Inverse Electron-Demand Diels - Alder Reactions with 1,2,4-Triazines. J. Org. Chem. 1993, 58, 516-519.
    • (1993) J. Org. Chem , vol.58 , pp. 516-519
    • Li, J.H.1    Snyder, J.K.2
  • 79
    • 0014072079 scopus 로고
    • 2,3-Dichloro-5,6-dicyanobenzoquinone and Its Reactions
    • (a) Walker, D.; Hiebert, J. D. 2,3-Dichloro-5,6-dicyanobenzoquinone and Its Reactions. Chem. Rev. 1967, 67, 153-195.
    • (1967) Chem. Rev , vol.67 , pp. 153-195
    • Walker, D.1    Hiebert, J.D.2
  • 80
    • 0024791039 scopus 로고
    • The Intramolecular Nitrile Imine Cycloaddition Route to Pyrazolo[1,5-a][1,4]benzodiazepines
    • (b) Bruché, L.; Zecchi, G. The Intramolecular Nitrile Imine Cycloaddition Route to Pyrazolo[1,5-a][1,4]benzodiazepines. Tetrahedron 1989, 45, 7427-7432.
    • (1989) Tetrahedron , vol.45 , pp. 7427-7432
    • Bruché, L.1    Zecchi, G.2
  • 81
    • 3042741556 scopus 로고
    • A Useful 12-I-5 Triacetoxyperiodinane (the Dess - Martin Periodinane) for the Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related 12-I-5 Species
    • Dess, D. B.; Martin, J. C. A Useful 12-I-5 Triacetoxyperiodinane (the Dess - Martin Periodinane) for the Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related 12-I-5 Species. J. Am. Chem. Soc. 1991, 113, 7277-7287.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 7277-7287
    • Dess, D.B.1    Martin, J.C.2
  • 82
    • 0038042134 scopus 로고    scopus 로고
    • An Expedient Route to the Tetrazole Analogues of α-Amino Acids
    • Demko, Z. P.; Sharpless, K. B. An Expedient Route to the Tetrazole Analogues of α-Amino Acids. Org. Lett. 2002, 4, 2525-2527.
    • (2002) Org. Lett , vol.4 , pp. 2525-2527
    • Demko, Z.P.1    Sharpless, K.B.2
  • 83
    • 0345708168 scopus 로고    scopus 로고
    • Modern Synthetic Methods for Copper-Mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S Bond Formation
    • (a) Ley, S. V.; Thomas, A. W. Modern Synthetic Methods for Copper-Mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S Bond Formation. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 5400-5449
    • Ley, S.V.1    Thomas, A.W.2
  • 84
    • 9244225109 scopus 로고    scopus 로고
    • Highly Efficient and Mild Copper-Catalyzed N- and C-Arylations with Aryl Bromides and Iodides
    • (b) Christau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Highly Efficient and Mild Copper-Catalyzed N- and C-Arylations with Aryl Bromides and Iodides. Chem. - Eur. J. 2004, 10, 5607-5622.
    • (2004) Chem. - Eur. J , vol.10 , pp. 5607-5622
    • Christau, H.-J.1    Cellier, P.P.2    Spindler, J.-F.3    Taillefer, M.4
  • 85
    • 4143104684 scopus 로고    scopus 로고
    • Copper-Diamine-Catalyzed N-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles
    • (c) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. Copper-Diamine-Catalyzed N-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles. J. Org. Chem. 2004, 69, 5578-5587.
    • (2004) J. Org. Chem , vol.69 , pp. 5578-5587
    • Antilla, J.C.1    Baskin, J.M.2    Barder, T.E.3    Buchwald, S.L.4
  • 86
    • 0037179184 scopus 로고    scopus 로고
    • Palladium-and Copper-Catalyzed Selective Arylation of 5-Aryltetrazoles by Diaryliodonium Salts
    • (a) Beletskaya, I. P.; Davydov, D. V.; Gorovoy, M. S. Palladium-and Copper-Catalyzed Selective Arylation of 5-Aryltetrazoles by Diaryliodonium Salts. Tetrahedron Lett. 2002, 43, 6221-6223.
    • (2002) Tetrahedron Lett , vol.43 , pp. 6221-6223
    • Beletskaya, I.P.1    Davydov, D.V.2    Gorovoy, M.S.3
  • 88
    • 0034622310 scopus 로고    scopus 로고
    • New Synthesis of Diaryliodonium Sulfonates from Arylboronic Acids
    • (c) Carroll, M. A.; Pike, V. W.; Widdowson, D. A. New Synthesis of Diaryliodonium Sulfonates from Arylboronic Acids. Tetrahedron Lett. 2000, 41, 5393-5396.
    • (2000) Tetrahedron Lett , vol.41 , pp. 5393-5396
    • Carroll, M.A.1    Pike, V.W.2    Widdowson, D.A.3
  • 89
    • 1842608758 scopus 로고    scopus 로고
    • Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B
    • Stangeland, E. L.; Sammakia, T. Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B. J. Org. Chem. 2004, 69, 2381-2385.
    • (2004) J. Org. Chem , vol.69 , pp. 2381-2385
    • Stangeland, E.L.1    Sammakia, T.2
  • 90
    • 0000889418 scopus 로고
    • Synthesis and Reactions of Lithiated Monocyclic Azoles Containing Two or More Hetero-Atoms. Part V: Isothiazoles and Thiazoles
    • For a review, see
    • (a) For a review, see Iddon, B. Synthesis and Reactions of Lithiated Monocyclic Azoles Containing Two or More Hetero-Atoms. Part V: Isothiazoles and Thiazoles. Heterocycles 1995, 41, 533-593.
    • (1995) Heterocycles , vol.41 , pp. 533-593
    • Iddon, B.1
  • 92
    • 1542345042 scopus 로고    scopus 로고
    • Synthesis and Evaluation of a Conformationally Constrained Pyridazinone PNA-monomer for Recognition of Thymine in Triple-Helix Structures
    • Olsen, A. G.; Dahl, O.; Nielsen, P. E. Synthesis and Evaluation of a Conformationally Constrained Pyridazinone PNA-monomer for Recognition of Thymine in Triple-Helix Structures. Bioorg. Med. Chem. Lett. 2004, 14, 1551-1554.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 1551-1554
    • Olsen, A.G.1    Dahl, O.2    Nielsen, P.E.3
  • 93
    • 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
  • 94
    • 29044438582 scopus 로고    scopus 로고
    • Elucidation of Fatty Acid Amide Hydrolase Inhibition by Potent α-Ketoheterocycle Derivatives from Monte Carlo Simulations
    • (a) Guimaráes, C. R. W.; Boger, D. L.; Jorgensen, W. L. Elucidation of Fatty Acid Amide Hydrolase Inhibition by Potent α-Ketoheterocycle Derivatives from Monte Carlo Simulations. J. Am. Chem. Soc. 2005, 127, 17377-17384.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 17377-17384
    • Guimaráes, C.R.W.1    Boger, D.L.2    Jorgensen, W.L.3
  • 95
    • 33845923661 scopus 로고    scopus 로고
    • Elucidation of Hydrolysis Mechanisms for Fatty Acid Amide Hydrolase and its Lys142Ala Variant via QMZMM Simulations
    • (b) Tubert-Brohman, I.; Acevedo, O.; Jorgensen, W. L. Elucidation of Hydrolysis Mechanisms for Fatty Acid Amide Hydrolase and its Lys142Ala Variant via QMZMM Simulations. J. Am. Chem. Soc. 2006, 128, 16904-16913.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16904-16913
    • Tubert-Brohman, I.1    Acevedo, O.2    Jorgensen, W.L.3
  • 96
    • 0035799319 scopus 로고    scopus 로고
    • Profiling Serine Hydrolase Activities in Complex Proteomes
    • (a) Kidd, D.; Liu, Y.; Cravatt, B. F. Profiling Serine Hydrolase Activities in Complex Proteomes. Biochemistry 2001, 40, 4005-4015.
    • (2001) Biochemistry , vol.40 , pp. 4005-4015
    • Kidd, D.1    Liu, Y.2    Cravatt, B.F.3
  • 97
    • 0033593013 scopus 로고    scopus 로고
    • Activity-Based Protein Profiling: The Serine Hydrolases
    • (b) Liu, Y.; Patricelli, M. P.; Cravatt, B. F. Activity-Based Protein Profiling: the Serine Hydrolases. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 14694-14699.
    • (1999) Proc. Natl. Acad. Sci. U.S.A , vol.96 , pp. 14694-14699
    • Liu, Y.1    Patricelli, M.P.2    Cravatt, B.F.3
  • 98
    • 33749671593 scopus 로고    scopus 로고
    • An Enzyme that Regulates Ether Lipid Signaling Pathways in Cancer Annotated by Multidimensional Profiling
    • Chiang, K. P.; Niessen, S.; Saghatelian, A.; Cravatt, B. F. An Enzyme that Regulates Ether Lipid Signaling Pathways in Cancer Annotated by Multidimensional Profiling. Chem. Biol. 2006, 13, 1041-1050.
    • (2006) Chem. Biol , vol.13 , pp. 1041-1050
    • Chiang, K.P.1    Niessen, S.2    Saghatelian, A.3    Cravatt, B.F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.