메뉴 건너뛰기




Volumn 57, Issue 14, 2014, Pages 6240-6251

Development of N -methyl-(2-arylquinolin-4-yl)oxypropanamides as leads to PET radioligands for translocator protein (18 kDa)

Author keywords

[No Author keywords available]

Indexed keywords

,N2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; 1 METHY 3 [(2 PHENYLQUINOLIN 4 YL)METHYL]PYRROLIDIN 2 ONE; 2 PHENYL 1,4 DIHYDRO 1,5 NAPHTHYRIDIN 4 ONE; 2 PHENYL 1,4 DIHYDROQUINAZOLIN 4 ONE; CARRIER PROTEIN; N (3 BROMOPYRIDIN 2 YL)BENZAMIDE; N (3 BROMOPYRIDIN 4 YL)BENZAMIDE; N (BUTAN 2 YL) N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YLPROPANAMIDE; N BENZYL N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; N BUTYL N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL) N PROPYLPROPANAMIDE; N ETHYL N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; N METHYL (2 ARYLQUINOLIN 4 YL)OXYPROPANAMIDE; N METHYL N PHENYL 2 SULFANYLPROPANAMIDE; N METHYL N PHENYL 2 [[2 (PYRIDIN 2 YL)QUINOLIN 4 YL]OXY]PROPANAMIDE; N PHENYL 2 [(2 PHENYLQUINOLIN 4 YL)SULFANYL]PROPANAMIDE; N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL) N (PROPAN 2 YL)PROPYLPROPANAMIDE; N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL) N (PYRIDIN 3 YL)PROPANAMIDE; N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL) N PROPYLPROPANAMIDE; N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL) N PYRIDIN 2 YL)PROPANAMIDE; N,2 DIMETHYL 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; N,2 DIMETHYL N (2 METHYLPROPYL) 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; N,2 DIMETHYL N PENTYL 3 (2 PHENYLQUINOLIN 4 YL) N PROPYLPROPANAMIDE; N,2 DIMETHYL N PHENYL 3 (2 PHENYLQUINOLIN 4YL)PROPANAMIDE; N,N DIETHYL 2 METHYL 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; N,N DIETHYL 2 [(2 PHENYLQUINOLIN 4 YL)METHYL]BUTANAMIDE; N,N DIETHYL 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; N,N,2 TRIMETHYL 3 (2 PHENYLQUINOLIN 4 YL)PROPANAMIDE; PROPIONAMIDE DERIVATIVE; RADIOLIGAND; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84904989440     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm5007947     Document Type: Article
Times cited : (22)

References (62)
  • 1
    • 0021953954 scopus 로고
    • Peripheral-type benzodiazepine receptors: Autoradiographic localization in whole-body sections of neonatal rats
    • Anholt, R. R. H.; De Souza, E. B.; Oster-Granite, M. L.; Snyder, S. H. Peripheral-type benzodiazepine receptors: autoradiographic localization in whole-body sections of neonatal rats J. Pharmacol. Exp. Ther. 1985, 233, 517-526
    • (1985) J. Pharmacol. Exp. Ther. , vol.233 , pp. 517-526
    • Anholt, R.R.H.1    De Souza, E.B.2    Oster-Granite, M.L.3    Snyder, S.H.4
  • 3
    • 0018347895 scopus 로고
    • Characterization of benzodiazepine binding sites in cultured cells of neural origin
    • Syapin, P. J.; Skolnick, P. Characterization of benzodiazepine binding sites in cultured cells of neural origin J. Neurochem. 1979, 32, 1047-1051
    • (1979) J. Neurochem. , vol.32 , pp. 1047-1051
    • Syapin, P.J.1    Skolnick, P.2
  • 4
    • 0026591024 scopus 로고
    • Isolation of the mitochondrial benzodiazepine receptor: Association with the voltage-dependent anion channel and the adenine nucleotide carrier
    • McEnery, M. W.; Snowman, A. M.; Trifiletti, R. R.; Snyder, S. H. Isolation of the mitochondrial benzodiazepine receptor: Association with the voltage-dependent anion channel and the adenine nucleotide carrier Proc. Natl. Acad. Sci. U. S. A. 1992, 89, 3170-3174
    • (1992) Proc. Natl. Acad. Sci. U. S. A. , vol.89 , pp. 3170-3174
    • McEnery, M.W.1    Snowman, A.M.2    Trifiletti, R.R.3    Snyder, S.H.4
  • 6
    • 0033080452 scopus 로고    scopus 로고
    • The effects of superoxide and the peripheral benzodiazepine receptor ligands on the mitochondrial processing of manganese-dependent superoxide dismutase
    • Wright, G.; Reichenbecher, V. The effects of superoxide and the peripheral benzodiazepine receptor ligands on the mitochondrial processing of manganese-dependent superoxide dismutase Exp. Cell Res. 1999, 246, 443-450
    • (1999) Exp. Cell Res. , vol.246 , pp. 443-450
    • Wright, G.1    Reichenbecher, V.2
  • 7
    • 33644498858 scopus 로고    scopus 로고
    • Peripheral-type benzodiazepine receptor in neurosteroid biosynthesis, neuropathology and neurological disorders
    • Papadopoulos, V.; Lecanu, L.; Brown, R. C.; Han, Z.; Yao, Z.-X. Peripheral-type benzodiazepine receptor in neurosteroid biosynthesis, neuropathology and neurological disorders Neuroscience 2006, 138, 749-756
    • (2006) Neuroscience , vol.138 , pp. 749-756
    • Papadopoulos, V.1    Lecanu, L.2    Brown, R.C.3    Han, Z.4    Yao, Z.-X.5
  • 8
    • 0028362187 scopus 로고
    • Induction of peripheral-type benzodiazepine receptors during differentiation of mouse erythroleukemia cells-a possible involvement of these receptors in heme biosynthesis
    • Taketani, S.; Kohno, H.; Okuda, M.; Furukawa, T.; Tokunaga, R. Induction of peripheral-type benzodiazepine receptors during differentiation of mouse erythroleukemia cells-a possible involvement of these receptors in heme biosynthesis J. Biol. Chem. 1994, 269, 7527-7531
    • (1994) J. Biol. Chem. , vol.269 , pp. 7527-7531
    • Taketani, S.1    Kohno, H.2    Okuda, M.3    Furukawa, T.4    Tokunaga, R.5
  • 9
    • 0023613207 scopus 로고
    • Peripheral type benzodiazepine binding sites are a sensitive indirect index of neuronal damage
    • Benavides, J.; Fage, D.; Carter, C.; Scatton, B. Peripheral type benzodiazepine binding sites are a sensitive indirect index of neuronal damage Brain Res. 1987, 421, 167-172
    • (1987) Brain Res. , vol.421 , pp. 167-172
    • Benavides, J.1    Fage, D.2    Carter, C.3    Scatton, B.4
  • 11
    • 0036850086 scopus 로고    scopus 로고
    • Visualising microglial activation in vivo
    • Banati, R. B. Visualising microglial activation in vivo Glia 2002, 40, 206-217
    • (2002) Glia , vol.40 , pp. 206-217
    • Banati, R.B.1
  • 17
    • 80055083184 scopus 로고    scopus 로고
    • Imaging brain microglial activation using positron emission tomography and translocator protein-specific radioligands
    • In; Guest, P. C. Bahn, S. Academic Press: Waltham, MA, Vol. - 39
    • Owen, D. R. J.; Matthews, P. M. Imaging brain microglial activation using positron emission tomography and translocator protein-specific radioligands. In Biomarkers of Neurological and Psychiatric Disease; Guest, P. C.; Bahn, S., Eds.; Academic Press: Waltham, MA, 2011; Vol. 101, pp 19-39.
    • (2011) Biomarkers of Neurological and Psychiatric Disease , vol.101 , pp. 19
    • Owen, D.R.J.1    Matthews, P.M.2
  • 18
    • 78651060446 scopus 로고
    • C-11 Labeling of PK11195 and visualization of peripheral receptors of benzodiazepines by positron-emission tomography
    • Camsonne, R.; Moulin, M. A.; Crouzel, C.; Syrota, A.; Maziere, M.; Comar, D. C-11 Labeling of PK11195 and visualization of peripheral receptors of benzodiazepines by positron-emission tomography J. Pharmacol. 1986, 17, 383
    • (1986) J. Pharmacol. , vol.17 , pp. 383
    • Camsonne, R.1    Moulin, M.A.2    Crouzel, C.3    Syrota, A.4    Maziere, M.5    Comar, D.6
  • 24
    • 78349311533 scopus 로고    scopus 로고
    • PET tracers for the peripheral benzodiazepine receptor and uses thereof
    • Schweitzer, P. J.; Fallon, B. A.; Mann, J. J.; Kumar, J. S. D. PET tracers for the peripheral benzodiazepine receptor and uses thereof Drug Discovery Today 2010, 15, 933-942
    • (2010) Drug Discovery Today , vol.15 , pp. 933-942
    • Schweitzer, P.J.1    Fallon, B.A.2    Mann, J.J.3    Kumar, J.S.D.4
  • 25
    • 77954362213 scopus 로고    scopus 로고
    • The development of PET radioligands for imaging the translocator protein (18 kDa): What have we learned?
    • Luus, C.; Hanani, R.; Reynolds, A.; Kassiou, M. The development of PET radioligands for imaging the translocator protein (18 kDa): What have we learned? J. Labelled Compd. Radiopharm. 2010, 53, 501-510
    • (2010) J. Labelled Compd. Radiopharm. , vol.53 , pp. 501-510
    • Luus, C.1    Hanani, R.2    Reynolds, A.3    Kassiou, M.4
  • 28
    • 38949112843 scopus 로고    scopus 로고
    • Kinetic analysis in healthy humans of a novel positron emission tomography radioligand to image the peripheral benzodiazepine receptor, a potential biomarker for inflammation
    • Fujita, M.; Imaizumi, M.; Zoghbi, S. S.; Fujimura, Y.; Farris, A. G.; Suhara, T.; Hong, J.; Pike, V. W.; Innis, R. B. Kinetic analysis in healthy humans of a novel positron emission tomography radioligand to image the peripheral benzodiazepine receptor, a potential biomarker for inflammation Neuroimage 2008, 40, 43-52
    • (2008) Neuroimage , vol.40 , pp. 43-52
    • Fujita, M.1    Imaizumi, M.2    Zoghbi, S.S.3    Fujimura, Y.4    Farris, A.G.5    Suhara, T.6    Hong, J.7    Pike, V.W.8    Innis, R.B.9
  • 37
    • 84856990480 scopus 로고    scopus 로고
    • Identifying improved TSPO PET imaging probes through biomathematics: The impact of multiple TSPO binding sites in vivo
    • Guo, Q.; Owen, D. R.; Rabiner, E. A.; Turkheimer, F. E.; Gunn, R. N. Identifying improved TSPO PET imaging probes through biomathematics: the impact of multiple TSPO binding sites in vivo NeuroImage 2012, 60, 902-910
    • (2012) NeuroImage , vol.60 , pp. 902-910
    • Guo, Q.1    Owen, D.R.2    Rabiner, E.A.3    Turkheimer, F.E.4    Gunn, R.N.5
  • 39
    • 0027241271 scopus 로고
    • Positron-emitting radioligands for studies in vivo-probes for human psychopharmacology
    • Pike, V. W. Positron-emitting radioligands for studies in vivo-probes for human psychopharmacology J. Psychopharmacol. 1993, 7, 139-158
    • (1993) J. Psychopharmacol. , vol.7 , pp. 139-158
    • Pike, V.W.1
  • 40
    • 0344983883 scopus 로고    scopus 로고
    • Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography
    • Laruelle, M.; Slifstein, M.; Huang, Y. Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography Mol. Imaging Biol. 2003, 5, 363-375
    • (2003) Mol. Imaging Biol. , vol.5 , pp. 363-375
    • Laruelle, M.1    Slifstein, M.2    Huang, Y.3
  • 41
    • 56549113643 scopus 로고    scopus 로고
    • In vivo site-directed radiotracers: A mini-review
    • Patel, S.; Gibson, R. In vivo site-directed radiotracers: a mini-review Nucl. Med. Biol. 2008, 35, 805-815
    • (2008) Nucl. Med. Biol. , vol.35 , pp. 805-815
    • Patel, S.1    Gibson, R.2
  • 42
    • 35748934487 scopus 로고    scopus 로고
    • The influence of drug-like concepts on decision-making in medicinal chemistry
    • Leeson, P. D.; Springthorpe, B. The influence of drug-like concepts on decision-making in medicinal chemistry Nature Rev. Drug Discovery 2007, 6, 881-890
    • (2007) Nature Rev. Drug Discovery , vol.6 , pp. 881-890
    • Leeson, P.D.1    Springthorpe, B.2
  • 44
    • 84885172160 scopus 로고    scopus 로고
    • Setting expectations in molecular optimizations: Strengths and limitations of commonly used composite parameters
    • Shultz, M. D. Setting expectations in molecular optimizations: strengths and limitations of commonly used composite parameters Bioorg. Med. Chem. Lett. 2013, 23, 5980-5991
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 5980-5991
    • Shultz, M.D.1
  • 45
    • 38149123939 scopus 로고    scopus 로고
    • Copper(I)- and gold(I)-catalyzed synthesis of 2,4-disubstituted quinoline derivatives from N -aryl-2-propynylamines
    • Kuninobu, Y.; Inoue, Y.; Takai, K. Copper(I)- and gold(I)-catalyzed synthesis of 2,4-disubstituted quinoline derivatives from N -aryl-2- propynylamines Chem. Lett. 2007, 36, 1422-1423
    • (2007) Chem. Lett. , vol.36 , pp. 1422-1423
    • Kuninobu, Y.1    Inoue, Y.2    Takai, K.3
  • 46
    • 0026010908 scopus 로고
    • PyBOP and PyBroP: Two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib
    • Frérot, E.; Coste, J.; Pantaloni, A.; Dufour, M.-N.; Jouin, P. PyBOP and PyBroP: two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib Tetrahedron 1991, 47, 259-270
    • (1991) Tetrahedron , vol.47 , pp. 259-270
    • Frérot, E.1    Coste, J.2    Pantaloni, A.3    Dufour, M.-N.4    Jouin, P.5
  • 47
    • 0000272976 scopus 로고
    • Isolation and reactions of α-lithio N, N -dimethylacetamide
    • Woodbury, R. P.; Rathke, M. W. Isolation and reactions of α-lithio N, N -dimethylacetamide J. Org. Chem. 1977, 42, 1688-1690
    • (1977) J. Org. Chem. , vol.42 , pp. 1688-1690
    • Woodbury, R.P.1    Rathke, M.W.2
  • 48
    • 33947445652 scopus 로고
    • A new process for the preparation of thioglycolylamides
    • VanAllan, J. A. A new process for the preparation of thioglycolylamides J. Am. Chem. Soc. 1947, 69, 2914
    • (1947) J. Am. Chem. Soc. , vol.69 , pp. 2914
    • Vanallan, J.A.1
  • 49
    • 0042338466 scopus 로고    scopus 로고
    • Use of highly active palladium-phosphinous acid catalysts in Stille, Heck, amination, and thiation reactions of chloroquinolines
    • Wolf, C.; Lerebours, R. Use of highly active palladium-phosphinous acid catalysts in Stille, Heck, amination, and thiation reactions of chloroquinolines J. Org. Chem. 2003, 68, 7077-7084
    • (2003) J. Org. Chem. , vol.68 , pp. 7077-7084
    • Wolf, C.1    Lerebours, R.2
  • 51
    • 0001073140 scopus 로고
    • Réduction d'azides par la triphénylphosphine en présence d'eau: Une méthode générale et chimiosélective d'accès aux amines primaires
    • Knouzi, N.; Vaultier, M.; Carrié, R. Réduction d'azides par la triphénylphosphine en présence d'eau: une méthode générale et chimiosélective d'accès aux amines primaires Bull. Soc. Chim. Fr. 1985, 122, 815-819
    • (1985) Bull. Soc. Chim. Fr. , vol.122 , pp. 815-819
    • Knouzi, N.1    Vaultier, M.2    Carrié, R.3
  • 52
    • 0023804034 scopus 로고
    • Efficient synthesis of peri -hydroxylated 9,10-anthracenedione ethers via alkylation of cesium phenolates
    • Winters, R. T.; Sercel, A. D.; Showalter, H. D. H. Efficient synthesis of peri -hydroxylated 9,10-anthracenedione ethers via alkylation of cesium phenolates Synthesis 1988, 712-714
    • (1988) Synthesis , pp. 712-714
    • Winters, R.T.1    Sercel, A.D.2    Showalter, H.D.H.3
  • 53
    • 27844466269 scopus 로고
    • N -Methoxy- N -methylamides as effective acylating agents
    • Nahm, S.; Weinreb, S. M. N -Methoxy- N -methylamides as effective acylating agents Tetrahedron Lett. 1981, 22, 3815-3818
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3815-3818
    • Nahm, S.1    Weinreb, S.M.2
  • 54
    • 84981759540 scopus 로고
    • Synthese von α- Und γ-oxychinolinen
    • Camps, R. Synthese von α- und γ-oxychinolinen Ber. Dtsch. Chem. Ges. 1899, 32, 3228-3234
    • (1899) Ber. Dtsch. Chem. Ges. , vol.32 , pp. 3228-3234
    • Camps, R.1
  • 55
    • 35348846488 scopus 로고    scopus 로고
    • Sequential Cu-catalyzed amidation-base-mediated Camps cyclization: A two-step synthesis of 2-aryl-4-quinolones from o -halophenones
    • Jones, C. P.; Anderson, K. W.; Buchwald, S. L. Sequential Cu-catalyzed amidation-base-mediated Camps cyclization: a two-step synthesis of 2-aryl-4-quinolones from o -halophenones J. Org. Chem. 2007, 72, 7968-7973
    • (2007) J. Org. Chem. , vol.72 , pp. 7968-7973
    • Jones, C.P.1    Anderson, K.W.2    Buchwald, S.L.3
  • 56
    • 79960049243 scopus 로고    scopus 로고
    • Determination of absolute configuration of chiral molecules using vibrational optical activity: A review
    • He, Y.; Wang, B.; Dukor, R. K.; Nafie, L. A. Determination of absolute configuration of chiral molecules using vibrational optical activity: a review Appl. Spectrosc. 2011, 65, 699-723
    • (2011) Appl. Spectrosc. , vol.65 , pp. 699-723
    • He, Y.1    Wang, B.2    Dukor, R.K.3    Nafie, L.A.4
  • 57
    • 0030869061 scopus 로고    scopus 로고
    • Mapping the peripheral benzodiazepine receptor binding site by conformationally restrained derivatives of 1-(2-chlorophenyl)- N -methyl- N -(1-methylpropyl)-3-isoquinolinecarboxamide (PK11195)
    • Cappelli, A.; Anzini, M.; Vomero, S.; De Benedetti, P. G.; Menziani, M. C.; Giorgi, G.; Manzoni, C. Mapping the peripheral benzodiazepine receptor binding site by conformationally restrained derivatives of 1-(2-chlorophenyl)- N -methyl- N -(1-methylpropyl)-3-isoquinolinecarboxamide (PK11195) J. Med. Chem. 1997, 40, 2910-2921
    • (1997) J. Med. Chem. , vol.40 , pp. 2910-2921
    • Cappelli, A.1    Anzini, M.2    Vomero, S.3    De Benedetti, P.G.4    Menziani, M.C.5    Giorgi, G.6    Manzoni, C.7
  • 58
    • 0027238911 scopus 로고
    • Radioligands for PET studies of central benzodiazepine receptors and PK (peripheral benzodiazepine) binding sites-current status
    • Pike, V. W.; Halldin, C.; Crouzel, C.; Barré, L.; Nutt, D. J.; Osman, S.; Shah, F.; Turton, D. R.; Waters, S. L. Radioligands for PET studies of central benzodiazepine receptors and PK (peripheral benzodiazepine) binding sites-current status Nucl. Med. Biol. 1993, 20, 503-525
    • (1993) Nucl. Med. Biol. , vol.20 , pp. 503-525
    • Pike, V.W.1    Halldin, C.2    Crouzel, C.3    Barré, L.4    Nutt, D.J.5    Osman, S.6    Shah, F.7    Turton, D.R.8    Waters, S.L.9
  • 59
    • 13844265035 scopus 로고    scopus 로고
    • Total synthesis of (-)-xyloketal D and its enantiomer-confirmation of absolute stereochemistry
    • Pettigrew, J. D.; Freeman, R. P.; Wilson, P. D. Total synthesis of (-)-xyloketal D and its enantiomer-confirmation of absolute stereochemistry Can. J. Chem. 2004, 82, 1640-1648
    • (2004) Can. J. Chem. , vol.82 , pp. 1640-1648
    • Pettigrew, J.D.1    Freeman, R.P.2    Wilson, P.D.3
  • 60
    • 84979194646 scopus 로고
    • Studien über Verkettungen. XXVI. das Aethylanilin
    • Bischoff, C. A. Studien über Verkettungen. XXVI. Das Aethylanilin Ber. Dtsch. Chem. Ges. 1897, 30, 3178-3180
    • (1897) Ber. Dtsch. Chem. Ges. , vol.30 , pp. 3178-3180
    • Bischoff, C.A.1
  • 62
    • 84904982044 scopus 로고
    • Ueber das Benzoyl- o -Amidobenzamid
    • Körner, M. Ueber das Benzoyl- o -Amidobenzamid J. Prakt. Chem. (Leipzig) 1887, 36, 155-165
    • (1887) J. Prakt. Chem. (Leipzig) , vol.36 , pp. 155-165
    • Körner, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.