메뉴 건너뛰기




Volumn 48, Issue 24, 2005, Pages 7808-7820

Adenosine kinase inhibitors. 6. Synthesis, water solubility, and antinociceptive activity of 5-phenyl-7-(5-deoxy-β-d-ribofuranosyl) pyrrolo[2,3-d]pyrimidines substituted at C4 with glycinamides and related compounds

Author keywords

[No Author keywords available]

Indexed keywords

4 (PHENYLAMINO) 5 PHENYL 7 (5 DEOXY BETA DEXTRO RIBOFURANOSYL)PYRROLO[2,3 D]PYRIMIDINE; 4 N (N CYCLOPROPYLCARBAMOYLMETHYL)AMINO 5 PHENYL 7 (5 DEOXY BETA DEXTRO RIBOFURANOSYL)PYRROLO[2,3 D]PYRIMIDINE; ADENOSINE KINASE INHIBITOR; BRADYKININ; GP 3269; UNCLASSIFIED DRUG;

EID: 28144445057     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050394a     Document Type: Article
Times cited : (60)

References (59)
  • 1
    • 0034721186 scopus 로고    scopus 로고
    • Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition and anti-seizure activity of 5-Iodotubercidin analogues
    • (a) Ugarkar, B. G.; DaRe, J. M.; Kopcho, J. J.; Browne, C. E. III; Schanzer, J. M.; Wiesner, J. B.; Erion, M. D. Adenosine Kinase Inhibitors. 1. Synthesis, Enzyme Inhibition and Anti-seizure Activity of 5-Iodotubercidin Analogues. J. Med. Chem. 2000, 43, 2883-2893.
    • (2000) J. Med. Chem. , vol.43 , pp. 2883-2893
    • Ugarkar, B.G.1    Dare, J.M.2    Kopcho, J.J.3    Browne III, C.E.4    Schanzer, J.M.5    Wiesner, J.B.6    Erion, M.D.7
  • 2
    • 0034721142 scopus 로고    scopus 로고
    • Adenosine kinase inhibitors. 2. Synthesis, enzyme inhibition and antiseizure activity of diaryltubercidin analogues
    • (b) Ugarkar, B. G.; Castellino, A. J.; DaRe, J. M.; Kopcho, J. J.; Wiesner, J. B.; Schanzer, J. M.; Erion, M. D. Adenosine Kinase Inhibitors. 2. Synthesis, Enzyme Inhibition and Antiseizure Activity of Diaryltubercidin Analogues. J. Med. Chem. 2000, 43, 2894-2905.
    • (2000) J. Med. Chem. , vol.43 , pp. 2894-2905
    • Ugarkar, B.G.1    Castellino, A.J.2    DaRe, J.M.3    Kopcho, J.J.4    Wiesner, J.B.5    Schanzer, J.M.6    Erion, M.D.7
  • 5
    • 0027935403 scopus 로고
    • Inhibition of adenosine kinase increases endogenous adenosine and depresses neuronal activity in hippocampal slices
    • (e) Pak, M. A.; Hass, H. L.; Decking, U. K. M.; Schrader, J. Inhibition of Adenosine Kinase Increases Endogenous Adenosine and Depresses Neuronal Activity in Hippocampal Slices. Neuropharmacology 1994, 33, 1049-1053.
    • (1994) Neuropharmacology , vol.33 , pp. 1049-1053
    • Pak, M.A.1    Hass, H.L.2    Decking, U.K.M.3    Schrader, J.4
  • 6
    • 0031692409 scopus 로고    scopus 로고
    • Delayed treatment with an adenosine kinase inhibitor, GP683, attenuates infarct size in rats with temporary middle cerebral artery occlusion
    • Tatlisumak, T.; Takano, K.; Carano, R.; Miller, L. P.; Foster, A. C.; Fisher, M. Delayed Treatment with an Adenosine Kinase Inhibitor, GP683, Attenuates Infarct Size in Rats with Temporary Middle Cerebral Artery Occlusion. Stroke 1998, 29, 1952-1958.
    • (1998) Stroke , vol.29 , pp. 1952-1958
    • Tatlisumak, T.1    Takano, K.2    Carano, R.3    Miller, L.P.4    Foster, A.C.5    Fisher, M.6
  • 7
    • 0142028908 scopus 로고    scopus 로고
    • Adenosine kinase inhibitors. 3. Synthesis, SAR and antiinflammatory activity of a series of L-Lyxofuranosyl nucleosides
    • (a) Ugarkar, B. G.; Castellino, A. J.; DaRe, J. S.; Ramirez-Weinhouse, M.; Kopcho, J. J.; Rosengren, S.; Erion, M. D. Adenosine Kinase Inhibitors. 3. Synthesis, SAR and Antiinflammatory Activity of a Series of L-Lyxofuranosyl Nucleosides. J. Med. Chem. 2003, 46, 4750-4760.
    • (2003) J. Med. Chem. , vol.46 , pp. 4750-4760
    • Ugarkar, B.G.1    Castellino, A.J.2    DaRe, J.S.3    Ramirez-Weinhouse, M.4    Kopcho, J.J.5    Rosengren, S.6    Erion, M.D.7
  • 11
    • 0028034410 scopus 로고
    • Adenosine kinase and adenosine deaminase inhibition modulate spinal adenosine- and opiod agonist-induced antinociception in mice
    • (a) Keil II, G. J.; DeLander, G. E. Adenosine kinase and adenosine deaminase inhibition modulate spinal adenosine- and opiod agonist-induced antinociception in mice. Eur. J. Pharmacol. 1994, 271, 37-46.
    • (1994) Eur. J. Pharmacol. , vol.271 , pp. 37-46
    • Keil II, G.J.1    DeLander, G.E.2
  • 12
    • 0038689146 scopus 로고    scopus 로고
    • Adenosine in the spinal cord and periphery: Release and regulation of pain
    • (b) Sawynok, J.; Liu, X. J. Adenosine in the spinal cord and periphery: Release and regulation of pain. Prog. Neurobiol. 2003, 69, 313-340.
    • (2003) Prog. Neurobiol. , vol.69 , pp. 313-340
    • Sawynok, J.1    Liu, X.J.2
  • 15
    • 0033680092 scopus 로고    scopus 로고
    • ABT-702 4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido[2, 3-d]pyrimidine, a novel orally effective adenosine kinase inhibitor with analgesic and anti-inflammatory properties: I. In vitro characterization and acute antinociceptive effects in the mouse
    • Jarvis, M. F.; Yu, H. X.; Kohlhaas, K.; Alexander, K.; Lee, C. H.; Jiang, M. Q.; Bhagwat, S. S.; Williams, M.; Kowaluk, E. A. ABT-702 (4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido[2,3-d]pyrimidine, a novel orally effective adenosine kinase inhibitor with analgesic and anti-inflammatory properties: I. In vitro characterization and acute antinociceptive effects in the mouse. J. Pharmacol. Exp. Ther. 2000, 295, 1156-1164.
    • (2000) J. Pharmacol. Exp. Ther. , vol.295 , pp. 1156-1164
    • Jarvis, M.F.1    Yu, H.X.2    Kohlhaas, K.3    Alexander, K.4    Lee, C.H.5    Jiang, M.Q.6    Bhagwat, S.S.7    Williams, M.8    Kowaluk, E.A.9
  • 17
    • 0026520040 scopus 로고
    • Adenosine receptors: Pharmacology, structure-activity relationships, and therapeutic potential
    • (a) Jacobson, K. A.; van Galen, P. J. M.; Williams, M. Adenosine Receptors: Pharmacology, Structure-Activity Relationships, and Therapeutic Potential. J. Med. Chem. 1992, 35, 407-422.
    • (1992) J. Med. Chem. , vol.35 , pp. 407-422
    • Jacobson, K.A.1    Van Galen, P.J.M.2    Williams, M.3
  • 18
    • 0000192810 scopus 로고
    • Adenosine receptors as pharmacological targets
    • (b) Erion, M. D. Adenosine Receptors as Pharmacological Targets. Annu. Rep. Med. Chem. 1993, 28, 295-304.
    • (1993) Annu. Rep. Med. Chem. , vol.28 , pp. 295-304
    • Erion, M.D.1
  • 20
    • 0034658221 scopus 로고    scopus 로고
    • Purinergic and pyrimidinergic receptors as potential drug targets
    • Williams, M.; Jarvis, M. F. Purinergic and pyrimidinergic receptors as potential drug targets. Biochem. Pharmacol. 2000, 59, 1173-1185.
    • (2000) Biochem. Pharmacol. , vol.59 , pp. 1173-1185
    • Williams, M.1    Jarvis, M.F.2
  • 21
    • 18244410426 scopus 로고    scopus 로고
    • Adenosine kinase inhibitors. 4. 6,8-Disubstituted purine nucleoside derivatives. Synthesis, conformation, and enzyme inhibition
    • (a) Bookser, B. C.; Matelich, M. C.; Ollis, K.; Ugarkar, B. G. Adenosine Kinase Inhibitors. 4. 6,8-Disubstituted Purine Nucleoside Derivatives. Synthesis, Conformation, and Enzyme Inhibition. J. Med. Chem. 2005, 48, 3389-3399.
    • (2005) J. Med. Chem. , vol.48 , pp. 3389-3399
    • Bookser, B.C.1    Matelich, M.C.2    Ollis, K.3    Ugarkar, B.G.4
  • 22
    • 0033585527 scopus 로고    scopus 로고
    • Discovery of AMP mimetics that exhibit high inhibitory potency and specificity for AMP deaminase
    • (b) Another approach to ARAs is by inhibition of AMP deaminase. See for example: Erion, M. D.; Kasibhatla, S. R.; Bookser, B. C.; van Poelje, P. D.; Reddy, M. R.; Gruber, H. E.; Appleman, J. R. Discovery of AMP Mimetics that Exhibit High Inhibitory Potency and Specificity for AMP Deaminase. J. Am. Chem. Soc. 1999, 121, 308-319.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 308-319
    • Erion, M.D.1    Kasibhatla, S.R.2    Bookser, B.C.3    Van Poelje, P.D.4    Reddy, M.R.5    Gruber, H.E.6    Appleman, J.R.7
  • 23
    • 0017643233 scopus 로고
    • The formalin test: A quantitative study of the analgesic effects of morphine, meperidine, and brainstem stimulation in rats and cats
    • Dubuisson, D.; Dennis, S. G. The formalin test: A quantitative study of the analgesic effects of morphine, meperidine, and brainstem stimulation in rats and cats. Pain 1977, 4, 161-164.
    • (1977) Pain , vol.4 , pp. 161-164
    • Dubuisson, D.1    Dennis, S.G.2
  • 24
    • 0000811019 scopus 로고
    • The evaluation of the analgesic action of pethidine hydrochloride (demeral)
    • Woolfe, G.; MacDonald, A. D. The evaluation of the analgesic action of pethidine hydrochloride (demeral) J. Pharmacol. Exp. Ther. 1944, 80, 300-307.
    • (1944) J. Pharmacol. Exp. Ther. , vol.80 , pp. 300-307
    • Woolfe, G.1    MacDonald, A.D.2
  • 25
    • 0002261078 scopus 로고
    • A method for determining loss of pain sensation
    • D'Amour, F. E.; Smith, D. L. A method for determining loss of pain sensation. J. Pharmacol. Exp. Ther. 1941, 72, 74-79.
    • (1941) J. Pharmacol. Exp. Ther. , vol.72 , pp. 74-79
    • D'Amour, F.E.1    Smith, D.L.2
  • 26
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3-23.
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-23
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 27
    • 0031741846 scopus 로고    scopus 로고
    • Physical chemical properties of oral drug candidates in the discovery and exploratory development settings
    • (a) Curatolo, W. Physical chemical properties of oral drug candidates in the discovery and exploratory development settings. Pharm. Sci. Technol. Today 1998, 1, 387-393.
    • (1998) Pharm. Sci. Technol. Today , vol.1 , pp. 387-393
    • Curatolo, W.1
  • 28
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • (b) Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44, 235-249.
    • (2000) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 235-249
    • Lipinski, C.A.1
  • 29
    • 0040284222 scopus 로고
    • Reaktion von malonsauredinitril mit α-aminoketonen
    • (a) Gewald, K. Reaktion von Malonsauredinitril mit α-Aminoketonen. Z. Chem. 1961, 1, 349.
    • (1961) Z. Chem. , vol.1 , pp. 349
    • Gewald, K.1
  • 30
    • 0023228883 scopus 로고
    • Synthesis of 8-Cyano-1,4-dihydro-4-oxopyrrolo[1,2-a]pyrimidine-3- carboxylic acids as potential antimicrobial agents
    • (b) Abdalla, G. M.; Sowell, J. W. Sr. Synthesis of 8-Cyano-1,4-dihydro-4- oxopyrrolo[1,2-a]pyrimidine-3-carboxylic Acids as Potential Antimicrobial Agents. J. Heterocycl. Chem. 1987, 24, 297-301.
    • (1987) J. Heterocycl. Chem. , vol.24 , pp. 297-301
    • Abdalla, G.M.1    Sowell Sr., J.W.2
  • 31
    • 0001072616 scopus 로고
    • Stereoselective preparations of ribofuranosyl chlorides and acetates. Solvent effects and stereoselectivity in the reaction of ribofuranosyl acetates with trimethylallylsilane
    • Wilcox, C. S.; Otoski, R. M. Stereoselective Preparations of Ribofuranosyl Chlorides and Acetates. Solvent Effects and Stereoselectivity in the Reaction of Ribofuranosyl Acetates with Trimethylallylsilane. Tetrahedron Lett. 1986, 27, 1011-1014.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1011-1014
    • Wilcox, C.S.1    Otoski, R.M.2
  • 33
    • 28144433533 scopus 로고    scopus 로고
    • Unpublished research
    • Use of the Vilsmeyer salt to prepare chloro sugars will be reported in detail elsewhere: Kopcho, J.; Ugarkar, B. G. Unpublished research.
    • Kopcho, J.1    Ugarkar, B.G.2
  • 34
    • 0034729743 scopus 로고    scopus 로고
    • Synthesis and cytokine modulation properties of pyrrolo[2,3-d]-4- pyrimidone nucleosides
    • Wang, G.; Ta, R. C.; Gunic, E.; Du, J.; Bard, J.; Pai, B. Synthesis and Cytokine Modulation Properties of Pyrrolo[2,3-d]-4-pyrimidone Nucleosides. J. Med. Chem. 2000, 43, 2566-2574.
    • (2000) J. Med. Chem. , vol.43 , pp. 2566-2574
    • Wang, G.1    Ta, R.C.2    Gunic, E.3    Du, J.4    Bard, J.5    Pai, B.6
  • 35
    • 28144440574 scopus 로고
    • Synthesis of 6-Succinioaminopurine
    • The synthesis of amino acid substituted nucleosides has precedent going back to the pioneering work of Carter and others: (a) Carter, C. E. Synthesis of 6-Succinioaminopurine. J. Biol. Chem. 1956, 223, 139-146.
    • (1956) J. Biol. Chem. , vol.223 , pp. 139-146
    • Carter, C.E.1
  • 36
    • 0001587240 scopus 로고
    • The synthesis of N-(6-Purinyl)amino acids. Amino acids with a single reactive amino group
    • (b) Ward, D. N.; Wade, J.; Walborg, E. F. Jr.; Osdene, T. S. The Synthesis of N-(6-Purinyl)amino Acids. Amino Acids with a Single Reactive Amino Group. J. Org. Chem. 1961, 26, 5000-5005.
    • (1961) J. Org. Chem. , vol.26 , pp. 5000-5005
    • Ward, D.N.1    Wade, J.2    Walborg Jr., E.F.3    Osdene, T.S.4
  • 37
    • 28144436483 scopus 로고
    • N-(2-Amino-9-β-D-ribofuranosyl-9H-purin-6-yl)-glycine. Preparation of a nucleoside derivative of an amino acid
    • Zorbach, W. W.; Tipson, R. S.; Eds.; John Wiley and Sons: New York, Chapter 90
    • Vickers, R. S.; Gerster, J. F.; Robins, R. K. N-(2-Amino-9-β-D- ribofuranosyl-9H-purin-6-yl)-glycine. Preparation of a Nucleoside Derivative of an Amino Acid in Synthetic Procedures in Nucleic Acid Chemistry; Zorbach, W. W.; Tipson, R. S.; Eds.; John Wiley and Sons: New York, 1968; pp. 281-282, Chapter 90.
    • (1968) Synthetic Procedures in Nucleic Acid Chemistry , pp. 281-282
    • Vickers, R.S.1    Gerster, J.F.2    Robins, R.K.3
  • 38
    • 0005519527 scopus 로고
    • Synthesis of pyrrolo[2,3-d]-pyrimidines. The aglycon of toyocamycin
    • (a) Taylor, E. C.; Hendess, R. W. Synthesis of Pyrrolo[2,3-d]- pyrimidines. The Aglycon of Toyocamycin. J. Am. Chem. Soc. 1965, 87, 1995-2003.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 1995-2003
    • Taylor, E.C.1    Hendess, R.W.2
  • 39
    • 0035953047 scopus 로고    scopus 로고
    • 7-Alkyl- And 7-Cycloalkyl-5-aryl-pyrrolo-[2,3-d]pyrimidines-potent inhibitors of the tyrosine kinase c-src
    • (b) Widler, L.; Green, J.; Missbach, M.; Susa, M.; Altmann, Eva 7-Alkyl- and 7-Cycloalkyl-5-aryl-pyrrolo-[2,3-d]pyrimidines-Potent Inhibitors of the Tyrosine Kinase c-Src. Bioorg. Med. Chem. Lett. 2001, 11, 849-852.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 849-852
    • Widler, L.1    Green, J.2    Missbach, M.3    Susa, M.4    Altmann, E.5
  • 41
    • 0015786868 scopus 로고
    • The synthesis and xanthine oxidase inhibitory activity of pyrazolo[3,4-d]pyrimidines
    • (a) Kobayashi, S. The Synthesis and Xanthine Oxidase Inhibitory Activity of Pyrazolo[3,4-d]pyrimidines. Chem. Pharm. Bull. 1973, 21, 941-951.
    • (1973) Chem. Pharm. Bull. , vol.21 , pp. 941-951
    • Kobayashi, S.1
  • 42
    • 84986535342 scopus 로고
    • Polarized ethylenes. IV [1]. Synthesis of polarized ethylenes using thioamides and methyl dithiocarboxylates and their application to the syntheses of pyrazoles, pyrimidines, pyrazolo-[3,4-d]pyrimidines and 5-Aza[2.2.3] cyclazines
    • (b) Tominaga, Y.; Matsuoka, Y.; Oniyama, Y.; Uchimura, Y.; Komiya, H.; Hirayama, M.; Kohra, S.; Hosomi, A. Polarized Ethylenes. IV [1]. Synthesis of Polarized Ethylenes Using Thioamides and Methyl Dithiocarboxylates and Their Application to the Syntheses of Pyrazoles, Pyrimidines, Pyrazolo-[3,4-d] pyrimidines and 5-Aza[2.2.3]cyclazines. J. Heterocycl. Chem. 1990, 27, 647-660.
    • (1990) J. Heterocycl. Chem. , vol.27 , pp. 647-660
    • Tominaga, Y.1    Matsuoka, Y.2    Oniyama, Y.3    Uchimura, Y.4    Komiya, H.5    Hirayama, M.6    Kohra, S.7    Hosomi, A.8
  • 45
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • (a) Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 46
    • 28144455260 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 2
    • (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 2.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
    • Suzuki, A.1
  • 47
    • 49349137641 scopus 로고
    • A mild, general method for conversion of esters to amides
    • (a) Basha, A.; Lipton, M.; Weinreb, S. M. A Mild, General Method for Conversion of Esters to Amides. Tetrahedron Lett. 1977, 4171-4174.
    • (1977) Tetrahedron Lett. , pp. 4171-4174
    • Basha, A.1    Lipton, M.2    Weinreb, S.M.3
  • 48
    • 84953502363 scopus 로고
    • An alternative procedure for the aluminum-mediated conversion of esters to amides
    • (b) Levin, J. I.; Turos, E.; Weinreb, S. M. An Alternative Procedure for the Aluminum-Mediated Conversion of Esters to Amides. Synth. Commun. 1982, 12, 989-993.
    • (1982) Synth. Commun. , vol.12 , pp. 989-993
    • Levin, J.I.1    Turos, E.2    Weinreb, S.M.3
  • 49
    • 0002234102 scopus 로고
    • Conversion of esters to amides with dimethylaluminum amides: N,N-dimethylcyclohexanecarboxamide
    • Lipton, M. F.; Basha, A.; Weinreb, S. M. Conversion of Esters to Amides with Dimethylaluminum Amides: N,N-Dimethylcyclohexanecarboxamide. Org. Synth. 1979, 59, 49-53.
    • (1979) Org. Synth. , vol.59 , pp. 49-53
    • Lipton, M.F.1    Basha, A.2    Weinreb, S.M.3
  • 50
    • 0017816363 scopus 로고
    • Studies on organophosphorous compounds XXI. The dimer of 2-methoxyphenylthionophosphine sulfide as thiation reagent. A new route to thiocarboxamides
    • (a) Scheibye, S.; Pedersen, B. S.; Lawesson, S.-O. Studies on Organophosphorous Compounds XXI. The Dimer of 2-Methoxyphenylthionophosphine Sulfide as Thiation Reagent. A New Route to Thiocarboxamides. Bull. Soc. Chim. Belg. 1978, 87, 229-238.
    • (1978) Bull. Soc. Chim. Belg. , vol.87 , pp. 229-238
    • Scheibye, S.1    Pedersen, B.S.2    Lawesson, S.-O.3
  • 51
    • 44349183414 scopus 로고
    • Thionation reactions of Lawesson's reagents
    • (b) For a review of the Lawesson's reagent see Cava, M. P.; Levinson, M. I. Thionation Reactions of Lawesson's Reagents. Tetrahedron 1985, 41, 5061-5087.
    • (1985) Tetrahedron , vol.41 , pp. 5061-5087
    • Cava, M.P.1    Levinson, M.I.2
  • 52
    • 28144449196 scopus 로고    scopus 로고
    • Unpublished research
    • Additional modified sugar and pyrazolopyrimidine diaryltubercidine analogues: Ugarkar, B. G.; Matelich, M. C.; Boyer, S. Unpublished research.
    • Ugarkar, B.G.1    Matelich, M.C.2    Boyer, S.3
  • 53
    • 84960959252 scopus 로고
    • A method for measurement of analgesic activity on inflamed tissue
    • Randal, L. O.; Selito, J. J. A method for measurement of analgesic activity on inflamed tissue. Arch. Int. Pharmacodyn. 1957, 111, 409-419.
    • (1957) Arch. Int. Pharmacodyn. , vol.111 , pp. 409-419
    • Randal, L.O.1    Selito, J.J.2
  • 54
    • 0021213510 scopus 로고
    • The formalin test: A tonic pain model in the primate
    • The use of bradykinin is a modification of a known procedure employing formalin: Alreja, M.; Mutalik, P.; Mayar, U.; Manchanda, S. K. The formalin test: A tonic pain model in the primate. Pain 1984, 20, 97-105.
    • (1984) Pain , vol.20 , pp. 97-105
    • Alreja, M.1    Mutalik, P.2    Mayar, U.3    Manchanda, S.K.4
  • 55
    • 0032506161 scopus 로고    scopus 로고
    • Structure of human adenosine kinase at 1.5 Å resolution
    • (a) Mathews, I. I.; Erion, M. D.; Ealick, S. E. Structure of Human Adenosine Kinase at 1.5 Å Resolution. Biochemistry 1998, 37, 15607-15620.
    • (1998) Biochemistry , vol.37 , pp. 15607-15620
    • Mathews, I.I.1    Erion, M.D.2    Ealick, S.E.3
  • 56
    • 0034681294 scopus 로고    scopus 로고
    • Crystal structures of toxoplasma gondii adenosine kinase reveal a novel catalytic mechanism and prodrug binding
    • (b) Schumacher, M. A.; Scott, D. M.; Mathews, I. I.; Ealick, S. E.; Roos, D. S.; Ullman, B.; Brennan, R. G. Crystal Structures of Toxoplasma gondii Adenosine Kinase Reveal a Novel Catalytic Mechanism and Prodrug Binding. J. Mol. Biol. 2000, 296, 549-567.
    • (2000) J. Mol. Biol. , vol.296 , pp. 549-567
    • Schumacher, M.A.1    Scott, D.M.2    Mathews, I.I.3    Ealick, S.E.4    Roos, D.S.5    Ullman, B.6    Brennan, R.G.7
  • 57
    • 0034006652 scopus 로고    scopus 로고
    • Crystal structure of adenosine kinase from toxoplasma gondii at 1.8 Å resolution
    • Cook, W. J.; DeLucas, L. J.; Chattopadhyay, D. Crystal structure of adenosine kinase from Toxoplasma gondii at 1.8 Å resolution. Protein Sci. 2000, 9, 704-712.
    • (2000) Protein Sci. , vol.9 , pp. 704-712
    • Cook, W.J.1    DeLucas, L.J.2    Chattopadhyay, D.3
  • 58
    • 84981809206 scopus 로고
    • Synthesis and characterization of μ-bis[N-(hydroxypropyl) glycinamidato(2-)]dicopper(II) and μ-bis-[N-(hydroxypropyl)-DL- alaninamidato(2-)]dicopper(II)
    • (a) Ojima, H.; Yamada, K. Synthesis and Characterization of μ-bis[N-(hydroxypropyl)glycinamidato(2-)]dicopper(II) and μ-bis-[N-(hydroxypropyl)-DL-alaninamidato(2-)]dicopper(II). Z. Anorg. Allg. Chem. 1970, 379, 322-8.
    • (1970) Z. Anorg. Allg. Chem. , vol.379 , pp. 322-328
    • Ojima, H.1    Yamada, K.2
  • 59
    • 84985225003 scopus 로고
    • Reactions of sugars and related polyfunctional compounds with amino acids. 2. N-Acylation of 3-Amino-1,2-propanediol with amino acids
    • (b) Angrick, M.; Rewicki, D. Reactions of Sugars and Related Polyfunctional Compounds with Amino Acids. 2. N-Acylation of 3-Amino-1,2-propanediol with Amino Acids. Liebigs Ann. Chem. 1982, 1394-1397.
    • (1982) Liebigs Ann. Chem. , pp. 1394-1397
    • Angrick, M.1    Rewicki, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.