메뉴 건너뛰기




Volumn 56, Issue 1, 2013, Pages 46-59

Development of second-generation indole-based dynamin GTPase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DYNAMIN I; DYNAMIN II; N ((1 (3 (DIMETHYLAMINO)PROPYL) 1H INDOL 3 YL)METHYL)DECAN 1 AMINE; N((1 (3 (DIMETHYLAMINO)PROPYL) 1H INDOL 3 YL)METHYL)DODECAN 1 AMINE; UNCLASSIFIED DRUG;

EID: 84872286835     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300844m     Document Type: Article
Times cited : (42)

References (56)
  • 2
    • 0342748583 scopus 로고    scopus 로고
    • Sequential steps in clathrin-mediated synaptic vesicle endocytosis
    • Brodin, L.; Low, P.; Shupliakov, O. Sequential steps in clathrin-mediated synaptic vesicle endocytosis Curr. Opin. Neurobiol. 2000, 10, 312-320
    • (2000) Curr. Opin. Neurobiol. , vol.10 , pp. 312-320
    • Brodin, L.1    Low, P.2    Shupliakov, O.3
  • 3
    • 0035826257 scopus 로고    scopus 로고
    • GTPase activity of dynamin and resulting conformation change are essential for endocytosis
    • Marks, B.; Stowell, M. H. B.; Vallis, Y.; Mills, I. G.; Gibson, A.; Hopkins, C. R.; McMahon, H. T. GTPase activity of dynamin and resulting conformation change are essential for endocytosis Nature 2001, 410, 231-235
    • (2001) Nature , vol.410 , pp. 231-235
    • Marks, B.1    Stowell, M.H.B.2    Vallis, Y.3    Mills, I.G.4    Gibson, A.5    Hopkins, C.R.6    McMahon, H.T.7
  • 4
    • 0034526495 scopus 로고    scopus 로고
    • Dynamin and its role in membrane fission
    • Hinshaw, J. E. Dynamin and its role in membrane fission Annu. Rev. Cell Dev. Biol. 2000, 16, 483-519
    • (2000) Annu. Rev. Cell Dev. Biol. , vol.16 , pp. 483-519
    • Hinshaw, J.E.1
  • 5
    • 0028898261 scopus 로고
    • Dynamin self-assembles into rings suggesting a mechanism for coated vesicle budding
    • Hinshaw, J. E.; Schmid, S. L. Dynamin self-assembles into rings suggesting a mechanism for coated vesicle budding Nature 1995, 374, 190-192
    • (1995) Nature , vol.374 , pp. 190-192
    • Hinshaw, J.E.1    Schmid, S.L.2
  • 6
    • 0033128097 scopus 로고    scopus 로고
    • Nucleotide-dependent conformational changes in dynamin: Evidence for a mechanochemical molecular spring
    • Stowell, M. H.; Marks, B.; Wigge, P.; McMahon, H. T. Nucleotide-dependent conformational changes in dynamin: evidence for a mechanochemical molecular spring Nature Cell Biol. 1999, 1, 27-32
    • (1999) Nature Cell Biol. , vol.1 , pp. 27-32
    • Stowell, M.H.1    Marks, B.2    Wigge, P.3    McMahon, H.T.4
  • 7
  • 8
    • 0034697319 scopus 로고    scopus 로고
    • Phosphorylation of dynamin i on Ser-795 by protein kinase C blocks its association with phospholipids
    • Powell, K. A.; Valova, V. A.; Malladi, C. S.; Jensen, O. N.; Larsen, M. R.; Robinson, P. J. Phosphorylation of dynamin I on Ser-795 by protein kinase C blocks its association with phospholipids J. Biol. Chem. 2000, 275, 11610-11617
    • (2000) J. Biol. Chem. , vol.275 , pp. 11610-11617
    • Powell, K.A.1    Valova, V.A.2    Malladi, C.S.3    Jensen, O.N.4    Larsen, M.R.5    Robinson, P.J.6
  • 10
    • 80053376521 scopus 로고    scopus 로고
    • The crystal structure of dynamin
    • Ford, M. G. J.; Jenni, S.; Nunnari, J. The crystal structure of dynamin Nature 2011, 477, 561-566
    • (2011) Nature , vol.477 , pp. 561-566
    • Ford, M.G.J.1    Jenni, S.2    Nunnari, J.3
  • 15
    • 0035920226 scopus 로고    scopus 로고
    • Induction of neuronal cell death by Rab5A-dependent endocytosis of alpha-synuclein
    • Sung, J. Y.; Kim, J.; Paik, S. R.; Park, J. H.; Ahn, Y. S.; Chung, K. C. Induction of neuronal cell death by Rab5A-dependent endocytosis of alpha-synuclein J. Biol. Chem. 2001, 276, 27441-27448
    • (2001) J. Biol. Chem. , vol.276 , pp. 27441-27448
    • Sung, J.Y.1    Kim, J.2    Paik, S.R.3    Park, J.H.4    Ahn, Y.S.5    Chung, K.C.6
  • 22
  • 25
    • 36348985073 scopus 로고    scopus 로고
    • Myristyl trimethyl ammonium bromide and octadecyl trimethyl ammonium bromide are surface-active small molecule dynamin inhibitors that block endocytosis mediated by dynamin i or dynamin II
    • Quan, A.; McGeachie, A. B.; Keating, D. J.; van Dam, E. M.; Rusak, J.; Chau, N.; Malladi, C. S.; Chen, C.; McCluskey, A.; Cousin, M. A.; Robinson, P. J. Myristyl trimethyl ammonium bromide and octadecyl trimethyl ammonium bromide are surface-active small molecule dynamin inhibitors that block endocytosis mediated by dynamin I or dynamin II Mol. Pharmacol. 2007, 72, 1425-1439
    • (2007) Mol. Pharmacol. , vol.72 , pp. 1425-1439
    • Quan, A.1    McGeachie, A.B.2    Keating, D.J.3    Van Dam, E.M.4    Rusak, J.5    Chau, N.6    Malladi, C.S.7    Chen, C.8    McCluskey, A.9    Cousin, M.A.10    Robinson, P.J.11
  • 27
    • 67749097922 scopus 로고    scopus 로고
    • Azido and diazarinyl analogues of bis-tyrphostin as asymmetrical inhibitors of dynamin GTPase
    • Odell, L. R.; Chau, N.; Mariana, A.; Graham, M. E.; Robinson, P. J.; McCluskey, A. Azido and diazarinyl analogues of bis-tyrphostin as asymmetrical inhibitors of dynamin GTPase ChemMedChem. 2009, 4, 1182-1188
    • (2009) ChemMedChem. , vol.4 , pp. 1182-1188
    • Odell, L.R.1    Chau, N.2    Mariana, A.3    Graham, M.E.4    Robinson, P.J.5    McCluskey, A.6
  • 28
    • 37849039269 scopus 로고    scopus 로고
    • From Spanish fly to room-temperature ionic liquids (RTILs): Synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs
    • Zhang, J.; Lawrance, G. A.; Chau, N.; Robinson, P. J.; McCluskey, A. From Spanish fly to room-temperature ionic liquids (RTILs): synthesis, thermal stability and inhibition of dynamin 1 GTPase by a novel class of RTILs New J. Chem. 2008, 32, 28-36
    • (2008) New J. Chem. , vol.32 , pp. 28-36
    • Zhang, J.1    Lawrance, G.A.2    Chau, N.3    Robinson, P.J.4    McCluskey, A.5
  • 35
    • 80955159780 scopus 로고    scopus 로고
    • Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation
    • Biradar, J. S.; Sasidhar, B. S. Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation Eur. J. Med. Chem. 2011, 46, 6112-6118
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 6112-6118
    • Biradar, J.S.1    Sasidhar, B.S.2
  • 38
    • 59649123396 scopus 로고    scopus 로고
    • Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino Michael/Knoevenagel condensation
    • Hayashi, Y.; Toyoshima, M.; Gotoh, H.; Ishikawa, H. Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino Michael/Knoevenagel condensation Org. Lett. 2009, 11, 45-48
    • (2009) Org. Lett. , vol.11 , pp. 45-48
    • Hayashi, Y.1    Toyoshima, M.2    Gotoh, H.3    Ishikawa, H.4
  • 39
    • 75749146215 scopus 로고    scopus 로고
    • Asymmetric Michael Additions of α-Cyanoacetates
    • Jautze, S.; Peters, R. Asymmetric Michael Additions of α-Cyanoacetates Synthesis 2010, 365-388
    • (2010) Synthesis , pp. 365-388
    • Jautze, S.1    Peters, R.2
  • 40
    • 0037156418 scopus 로고    scopus 로고
    • Green chemistry approaches to the Knoevenagel condensation: Comparison of ethanol, water and solvent free (dry grind) approaches
    • McCluskey, A.; Robinson, P. J.; Hill, T.; Scott, J. L.; Edwards, J. K. Green chemistry approaches to the Knoevenagel condensation: comparison of ethanol, water and solvent free (dry grind) approaches Tetrahedron Lett. 2002, 43, 3117-3120
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3117-3120
    • McCluskey, A.1    Robinson, P.J.2    Hill, T.3    Scott, J.L.4    Edwards, J.K.5
  • 41
    • 77950259989 scopus 로고    scopus 로고
    • Synthesis of diphenylamine-based novel fluorescent styryl colorants by Knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent
    • Sonawane, Y. A.; Phadtare, S. B.; Borse, B. N.; Jagtap, A. R.; Shankarling, G. S. Synthesis of diphenylamine-based novel fluorescent styryl colorants by Knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent Org. Lett. 2010, 12, 1456-1459
    • (2010) Org. Lett. , vol.12 , pp. 1456-1459
    • Sonawane, Y.A.1    Phadtare, S.B.2    Borse, B.N.3    Jagtap, A.R.4    Shankarling, G.S.5
  • 42
    • 33746283173 scopus 로고    scopus 로고
    • Microwave flow chemistry: The next evolutionary step in synthetic chemistry?
    • Baxendale, I. R.; Pitts, M. R. Microwave flow chemistry: the next evolutionary step in synthetic chemistry? Chim. Oggi 2006, 24, 41-45
    • (2006) Chim. Oggi , vol.24 , pp. 41-45
    • Baxendale, I.R.1    Pitts, M.R.2
  • 43
    • 48149109607 scopus 로고    scopus 로고
    • Chemistry strategies in early drug discovery: An overview of recent trends
    • Colombo, M.; Peretto, I. Chemistry strategies in early drug discovery: an overview of recent trends Drug Discovery Today 2008, 13, 677-684
    • (2008) Drug Discovery Today , vol.13 , pp. 677-684
    • Colombo, M.1    Peretto, I.2
  • 44
    • 70350650700 scopus 로고    scopus 로고
    • Novel Process Windows - Gate to Maximizing Process Intensification via Flow Chemistry
    • Hessel, V. Novel Process Windows-Gate to Maximizing Process Intensification via Flow Chemistry Chem. Eng. Technol. 2009, 32, 1655-1681
    • (2009) Chem. Eng. Technol. , vol.32 , pp. 1655-1681
    • Hessel, V.1
  • 45
    • 79952361868 scopus 로고    scopus 로고
    • A flow chemistry route to 2-phenyl-3-(1 H -pyrrol-2-yl)propan-1-amines
    • Tarleton, M.; McCluskey, A. A flow chemistry route to 2-phenyl-3-(1 H -pyrrol-2-yl)propan-1-amines Tetrahedron Lett. 2011, 52, 1583-1586
    • (2011) Tetrahedron Lett. , vol.52 , pp. 1583-1586
    • Tarleton, M.1    McCluskey, A.2
  • 47
  • 48
    • 37549003699 scopus 로고    scopus 로고
    • Asymmetric Mannich reaction of dicarbonyl compounds with alpha-amido sulfones catalyzed by cinchona alkaloids and synthesis of chiral dihydropyrimidones
    • Lou, S.; Dai, P.; Schaus, S. E. Asymmetric Mannich reaction of dicarbonyl compounds with alpha-amido sulfones catalyzed by cinchona alkaloids and synthesis of chiral dihydropyrimidones J. Org. Chem. 2007, 72, 9998-10008
    • (2007) J. Org. Chem. , vol.72 , pp. 9998-10008
    • Lou, S.1    Dai, P.2    Schaus, S.E.3
  • 49
    • 33645772257 scopus 로고    scopus 로고
    • Practical synthesis of (S)-pyrrolidin-2-yl-1 H -tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis
    • Franckevicius, V.; Knudsen, K. R.; Ladlow, M.; Longbottom, D. A.; Ley, S. V. Practical synthesis of (S)-pyrrolidin-2-yl-1 H -tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis Synlett 2006, 889-892
    • (2006) Synlett , pp. 889-892
    • Franckevicius, V.1    Knudsen, K.R.2    Ladlow, M.3    Longbottom, D.A.4    Ley, S.V.5
  • 50
    • 33845526401 scopus 로고    scopus 로고
    • Selective catalytic hydrogenations in a microfluidics-based high throughput flow reactor on ion-exchange supported transition metal complexes: A modular approach to the heterogenization of soluble complex catalysts
    • Horvath, H. H.; Papp, G.; Csajagi, C.; Joo, F. Selective catalytic hydrogenations in a microfluidics-based high throughput flow reactor on ion-exchange supported transition metal complexes: A modular approach to the heterogenization of soluble complex catalysts Catal. Commun. 2007, 8, 442-446
    • (2007) Catal. Commun. , vol.8 , pp. 442-446
    • Horvath, H.H.1    Papp, G.2    Csajagi, C.3    Joo, F.4
  • 51
    • 31544463062 scopus 로고    scopus 로고
    • Continuous-flow high pressure hydrogenation reactor for optimization and high-throughput synthesis
    • Jones, R. V.; Godorhazy, L.; Varga, N.; Szalay, D.; Urge, L.; Darvas, F. Continuous-flow high pressure hydrogenation reactor for optimization and high-throughput synthesis J. Comb. Chem. 2006, 8, 110-116
    • (2006) J. Comb. Chem. , vol.8 , pp. 110-116
    • Jones, R.V.1    Godorhazy, L.2    Varga, N.3    Szalay, D.4    Urge, L.5    Darvas, F.6
  • 52
    • 33746035678 scopus 로고    scopus 로고
    • Continuous enantioselective hydrogenation of activated ketones on a Pt-CD chiral catalyst: Use of H-cube reactor system
    • Szollosi, G.; Herman, B.; Fulop, F.; Bartok, M. Continuous enantioselective hydrogenation of activated ketones on a Pt-CD chiral catalyst: use of H-cube reactor system React. Kinet. Catal. Lett. 2006, 88, 391-398
    • (2006) React. Kinet. Catal. Lett. , vol.88 , pp. 391-398
    • Szollosi, G.1    Herman, B.2    Fulop, F.3    Bartok, M.4
  • 53
    • 33845282801 scopus 로고
    • An assessment of the causes of the "cesium effect"
    • Dijkstra, G.; Kruizinga, W. H.; Kellogg, R. M. An assessment of the causes of the "cesium effect" J. Org. Chem. 1987, 52, 4230-4234
    • (1987) J. Org. Chem. , vol.52 , pp. 4230-4234
    • Dijkstra, G.1    Kruizinga, W.H.2    Kellogg, R.M.3
  • 54
    • 0030668143 scopus 로고    scopus 로고
    • Ubiquitously expressed dynamin-II has a higher intrinsic GTPase activity and a greater propensity for self-assembly than neuronal dynamin-I
    • Warnock, D. E.; Baba, T.; Schmid, S. L. Ubiquitously expressed dynamin-II has a higher intrinsic GTPase activity and a greater propensity for self-assembly than neuronal dynamin-I Mol. Biol. Cell 1997, 8, 2553-2562
    • (1997) Mol. Biol. Cell , vol.8 , pp. 2553-2562
    • Warnock, D.E.1    Baba, T.2    Schmid, S.L.3
  • 56
    • 33845668299 scopus 로고    scopus 로고
    • Effects of chlorpromazine on plasma membrane permeability and fluidity in the rat brain: A dynamic positron autoradiography and fluorescence polarization study
    • Maruoka, N.; Murata, T.; Omata, N.; Takashima, Y.; Tanii, H.; Yonekura, Y.; Fujibayashi, Y.; Wada, Y. Effects of chlorpromazine on plasma membrane permeability and fluidity in the rat brain: a dynamic positron autoradiography and fluorescence polarization study Prog. Neuropsychopharmacol. Biol. Psychiatry 2007, 31, 178-186
    • (2007) Prog. Neuropsychopharmacol. Biol. Psychiatry , vol.31 , pp. 178-186
    • Maruoka, N.1    Murata, T.2    Omata, N.3    Takashima, Y.4    Tanii, H.5    Yonekura, Y.6    Fujibayashi, Y.7    Wada, Y.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.