Novel quinazoline-urea analogues as modulators for Aβ-induced mitochondrial dysfunction: Design, synthesis, and molecular docking study

European Journal of Medicinal Chemistry

Volumn 84, Issue , 2014, Pages 466-475

  Elkamhawy, Ahmed ^a,b   Lee, Jiyoun ^c   Park, Beoung Geon ^a,d   Park, Insun ^a,e   Pae, Ae Nim ^a   Roh, Eun Joo ^a,b  

^a Korea Institute of Science and Technology   (South Korea)

^b University of Science and Technology (UST)   (South Korea)

^c Sungshin Women's University   (South Korea)

^d Korea University   (South Korea)

^e Yonsei University   (South Korea)

Author keywords

Alzheimer's disease (AD); Cyclophilin D (CypD); Mitochondrial permeability transition pore (mPTP); Molecular docking; Quinazoline urea; amyloid peptide (A )

Indexed keywords

1 (3 CHLOROPHENYL) 3 [6 (2 FLUOROBENZYLOXY)QUINAZOLIN 7 YL]UREA; 1 (3 CHLOROPHENYL) 3 [6 (4 FLUOROBENZYLOXY)QUINAZOLIN 7 YL]UREA; 1 (3,4 DICHLOROPHENYL) 3 [6 (4 FLUOROBENZYLOXY)QUINAZOLIN 7 YL]UREA; 1 [6 (2 CHLOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (2 FLUOROPHENYL)UREA; 1 [6 (2 CHLOROBENZYLOXY)QUINAZOLIN 7 YL] 3 PARA TOLYLUREA; 1 [6 (2 CHLOROBENZYLOXY)QUINAZOLIN 7 YL] 3 [4 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [6 (2 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (3 FLUOROPHENYL)UREA; 1 [6 (2 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (NAPHTHALEN 1 YL)UREA; 1 [6 (2 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 PARA TOLYLUREA; 1 [6 (2 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 [4 ( FLUROMETHYL)PHENYL]UREA; 1 [6 (3 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (3 FLUROPHENYL); 1 [6 (3 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 PARA TOLYLUREA; 1 [6 (4 CHLOROBENZYLOXY)QUINAZOLIN 7 YL) 3 (3,4 DICHLOROPHENYL)UREA; 1 [6 (4 CHLOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (2 FLUOROPHENYL)UREA; 1 [6 (4 CHLOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (3 FLUOROPHENYL)UREA; 1 [6 (4 CHLOROBENZYLOXY)QUINAZOLIN 7 YL] 3 PARA TOLYLUREA; 1 [6 (4 CHLOROBENZYLOXY)QUINAZOLIN 7 YL] 3 [4 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [6 (4 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (2 FLUOROPHENYL)UREA; 1 [6 (4 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 (3 FLUOROPHENYL)UREA; 1 [6 (4 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 PARA TOLYLUREA; 1 [6 (4 FLUOROBENZYLOXY)QUINAZOLIN 7 YL] 3 [4 (TRIFLUOROMETHYL)PHENYL]UREA; 1 [6 (BENZYLOXY)QUINAZOLIN 7 YL] 3 (3 FLUOROPHENYL)UREA; 1 [6 (BENZYLOXY)QUINAZOLIN 7 YL] 3 (3,4 DICHLOROPHENYL)UREA; 1 [6 (BENZYLOXY)QUINAZOLIN 7 YL] 3 (NAPHTHALEN 1 YL)UREA; 1 [6 (BENZYLOXY)QUINAZOLIN 7 YL] 3 PARA TOLYLUREA; AMYLOID BETA PROTEIN; CYCLOSPORIN A; MITOCHONDRIAL PERMEABILITY TRANSITION PORE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE; CARRIER PROTEIN; UREA;

ANIMAL CELL; ARTICLE; BRAIN CELL; CELL SURVIVAL; CELL VIABILITY; COMPUTER MODEL; CONTROLLED STUDY; DISORDERS OF MITOCHONDRIAL FUNCTIONS; DRUG ABSORPTION; DRUG DESIGN; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG LIKENESS; DRUG METABOLISM; DRUG SCORE; DRUG SYNTHESIS; HIPPOCAMPUS; IN VITRO STUDY; MITOCHONDRIAL MEMBRANE POTENTIAL; MOLECULAR DOCKING; MOUSE; MTT ASSAY; NONHUMAN; PHARMACOLOGICAL PARAMETERS; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; HUMAN; METABOLISM; MITOCHONDRION; STRUCTURE ACTIVITY RELATION;

AMYLOID BETA-PEPTIDES; CELL SURVIVAL; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HUMANS; MITOCHONDRIA; MITOCHONDRIAL MEMBRANE TRANSPORT PROTEINS; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; UREA;

EID: 84904900475     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.07.027     Document Type: Article

References (25)

1. http://www.who.int/mediacentre/factsheets/fs362/en/index.html, in.
2. L.O.N. White, H. Petrovitch, J. Hardman, J. Nelson, D.G. Davis, G.W. Ross, K. Masaki, L. Launer, and W.R. Markesbery Cerebrovascular pathology and dementia in autopsied Honolulu-Asia aging study participants Ann. N. Y. Acad. Sci. 977 2002 9 23 (Pubitemid 35418132)
3. Pathological correlates of late-onset dementia in a multicentre, community-based population in England and Wales. Neuropathology Group of the Medical Research Council Cognitive Function and Ageing Study (MRC CFAS) Lancet 357 2001 169 175
4. D. Aarsland, K. Andersen, and J. Larsen et al. The rate of cognitive decline in Parkinson disease Arch. Neurol. 61 2004 1906 1911 (Pubitemid 39612951)
5. A. Barker, M. Liddell, and M.J. Owen Role of amyloid β-protein in Alzheimer's disease Lancet 340 1992 850 851
6. W. Cerpa, M.C. Dinamarca, and N.C. Inestrosa Structure-function implications in Alzheimer's disease: effect of Abeta oligomers at central synapses Curr. Alzheimer Res. 5 2008 233 243 (Pubitemid 351840275)
7. H. Du, L. Guo, F. Fang, D. Chen, A.A. Sosunov, G.M. McKhann, Y. Yan, C. Wang, H. Zhang, J.D. Molkentin, F.J. Gunn-Moore, J.P. Vonsattel, O. Arancio, J.X. Chen, and S.D. Yan Cyclophilin D deficiency attenuates mitochondrial and neuronal perturbation and ameliorates learning and memory in Alzheimer's disease Nat. Med. 14 2008 1097 1105
8. P.H. Reddy, and M.F. Beal Amyloid beta, mitochondrial dysfunction and synaptic damage: implications for cognitive decline in aging and Alzheimer's disease Trends Mol. Med. 14 2008 45 53
9. P. Bernardi Mitochondrial transport of cations: channels, exchangers, and permeability transition Physiol. Rev. 79 1999 1127 1155 (Pubitemid 29473313)
10. A.A. Starkov, and F.M. Beal Portal to Alzheimer's disease Nat. Med. 14 2008 1020 1021
11. C. Chinopoulos, A.A. Starkov, and G. Fiskum Cyclosporin a-insensitive permeability transition in brain mitochondria: inhibition by 2-aminoethoxydiphenyl borate J. Biol. Chem. 278 2003 27382 27389 (Pubitemid 36899919)
12. Z. Zhong, T.P. Theruvath, R.T. Currin, P.C. Waldmeier, and J.J. Lemasters NIM811, a mitochondrial permeability transition inhibitor, prevents mitochondrial depolarization in small-for-size rat liver grafts Am. J. Transplant. 7 2007 1103 1111 (Pubitemid 46643118)
13. M.W. Harding, R.E. Handschumacher, and D.W. Speicher Isolation and amino acid sequence of cyclophilin J. Biol. Chem. 261 1986 8547 8555 (Pubitemid 17202738)
14. J.-F. Guichou, J. Viaud, C. Mettling, G. Subra, Y.-L. Lin, and A. Chavanieu Structure-based design, synthesis, and biological evaluation of novel inhibitors of human cyclophilin A J. Med. Chem. 49 2006 900 910 (Pubitemid 43221638)
15. J. Kim, J. Lee, B. Moon, I. Mook-Jung, G. Nam, G. Keum, A.N. Pae, and H. Choo pyridyl-urea derivatives as blockers of Aβ-induced mPTP opening for Alzheimer's disease Bull. Korean Chem. Soc. 33 2012 3887 3888
16. Y.S. Kim, S.h. Jung, B.-G. Park, M.K. Ko, H.-S. Jang, K. Choi, J.-H. Baik, J. Lee, J.K. Lee, A.N. Pae, Y.S. Cho, and S.-J. Min Synthesis and evaluation of oxime derivatives as modulators for amyloid beta-induced mitochondrial dysfunction Eur. J. Med. Chem. 62 2013 71 83
17. A. Chilin, G. Marzaro, S. Zanatta, V. Barbieri, G. Pastorini, P. Manzini, and A. Guiotto A new access to quinazolines from simple anilines Tetrahedron 62 2006 12351 12356 (Pubitemid 44738933)
18. S.T. Smiley, M. Reers, C. Mottola-Hartshorn, M. Lin, A. Chen, T.W. Smith, G.D. Steele, and L.B. Chen Intracellular heterogeneity in mitochondrial membrane potentials revealed by a J-aggregate-forming lipophilic cation JC-1 Proc. Natl. Acad. Sci. 88 1991 3671 3675 (Pubitemid 21916685)
19. B.K. Wagner, T. Kitami, T.J. Gilbert, D. Peck, A. Ramanathan, S.L. Schreiber, T.R. Golub, and V.K. Mootha Large-scale chemical dissection of mitochondrial function Nat. Biotechnol. 26 2008 343 351 (Pubitemid 351355127)
20. https://www.ccdc.cam.ac.uk/Solutions/GoldSuite/Pages/GOLD.aspx, in.
21. http://www.rcsb.org/pdb/explore/explore.do?structureId=2Z6W, in.
22. D.E. Clark, and S.D. Pickett Computational methods for the prediction of 'drug-likeness' Drug Discov. Today 5 2000 49 58
23. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Deliv. Rev. 23 1997 3 25 (Pubitemid 27046991)
24. http://www.organic-chemistry.org/prog/peo/, in.
25. I.V. Tetko Computing chemistry on the web Drug Discov. Today 10 2005 1497 1500 (Pubitemid 41527191)