Probing the mid-gorge of cholinesterases with spacer-modified bivalent quinazolinimines leads to highly potent and selective butyrylcholinesterase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 3, 2011, Pages 1222-1235

  Chen, Xinyu ^a,b   Tikhonova, Irina G ^a   Decker, Michael ^a,b  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^b UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Alzheimer's disease; Bivalent inhibitors; Cholinesterase; Molecular docking; Quinazolinimines

Indexed keywords

2 ACETAMIDO N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO [2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9,10, 11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENE AMINO)PROPYL)ACETAMIDE; 3 METHYL N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO [2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9, 10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL)BUTANAMIDE; 4 METHYL N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO [2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9, 10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL)PENTANAMIDE; AMIDE; AMINE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; N (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENE) N (3 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)PROPYL) N METHYLPROPANE 1,3 DIAMINE; N (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENE) N (3-(2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)PROPYL) N METHYLBUTANE 1,4 DIAMINE; N (4 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)BUTYL) N (3 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)PROPYL) METHACRYLAMIDE; N (4 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)BUTYL) N (3 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)PROPYL) PROPIONAMIDE; N (4 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)BUTYL) N (3 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)PROPYL)ACETAMIDE; N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL) ACETAMIDE; N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL) METHACRYLAMIDE; N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL) PENTANAMIDE; N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL) PIVALAMIDE; N (4 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)BUTYL) N (3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL) PROPIONAMIDE; N METHYL N (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENE) N (3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL) BUTANE 1,4 DIAMINE; N METHYL N (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENE) N (3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL)PROPANE 1,3 DIAMINE; N,N BIS(3 (2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) YLIDENEAMINO)PROPYL) ACETAMIDE; N,N BIS(3 (8,9,10,11 TETRAHYDRO 6H AZOCINO[2,1 B]QUINAZOLIN 13(7H) YLIDENEAMINO)PROPYL)ACETAMIDE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG BINDING; DRUG INHIBITION; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DOCKING;

ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; CHOLINESTERASES; COLORIMETRY; DRUG DESIGN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOLECULAR TARGETED THERAPY; PHYSICOCHEMICAL PHENOMENA; PROTEIN BINDING; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79551469089     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.12.034     Document Type: Article

References (36)

1. P.T. Francis, A.M. Palmer, M. Snape, and G.K. Wilcock J. Neurol. Neurosurg. Psychiatry 66 1999 137
2. C.N. Johnson, A. Roland, and N. Upton Drug Discov. Today: Ther. Strag. 1 2004 13
3. K.A. Carson, C. Geula, and M.M. Mesulam Brain Res. 540 1991 204
4. M.M. Mesulam, A. Guillozet, P. Shaw, A. Levey, E.G. Duysen, and O. Lockridge Neuroscience 110 2002 627
5. N.H. Creig, T. Utsuki, Q.-S. Yu, X. Zhu, H.W. Holloway, T. Perry, B. Lee, D.K. Ingram, and D.K. Lahiri Curr. Med. Res. Opin. 17 2001 1
6. N.H. Greig, T. Utsuki, D.K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q.S. Yu, J. Mamczarz, H.W. Holloway, T. Giordano, D. Chen, K. Furukawa, K. Sambamurti, A. Brossi, and D.K. Lahiri Proc. Natl. Acad. Sci. U.S.A. 102 2005 17213
7. L. Pisani, M. Catto, I. Giangreco, F. Leonetti, O. Nicolloti, A. Stefanachi, S. Cellamare, and A. Carotti ChemMedChem 5 2010 1616
8. M. Decker Mini-Rev. Med. Chem. 7 2007 221 and references cited therein
9. A. Cavalli, M.L. Bolognesi, A. Minarini, M. Rosini, V. Tumiatti, M. Recanatini, and C. Melchiorre J. Med. Chem. 51 2008 347 and references cited therein
10. U. Holzgrabe, P. Kapkova, V. Alptuezuen, J. Scheiber, and E. Kugelmann Expert Opin. Ther. Targets 11 2007 161 and references cited therein
11. M. Decker, Y.G. Si, B.I. Knapp, J.M. Bidlack, and J.L. Neumeyer J. Med. Chem. 53 2010 402
12. M. Decker, and J. Lehmann Curr. Top. Med. Chem. 7 2007 347
13. F. Leonetti, M. Catto, O. Nicolotti, L. Pisani, A. Cappa, A. Stefanachi, and A. Carotti Bioorg. Med. Chem. 16 2008 7450
14. D. Munoz-Torrero, and P. Camps Curr. Med. Chem. 13 2006 399
15. M. Schulze, O. Siol, M. Decker, and J. Lehmann Bioorg. Med. Chem. Lett. 20 2010 2946
16. M. Decker J. Med. Chem. 49 2006 5411
17. G. Campiani, C. Fattorusso, S. Butini, A. Gaeta, M. Agnusdei, S. Gemma, M. Persico, B. Catalanotti, L. Savini, V. Nacci, E. Novellino, H.W. Holloway, N.H. Greig, T. Belinskaya, J.M. Fedorko, and A. Saxena J. Med. Chem. 48 2005 1919
18. S. Butini, G. Campiani, M. Borrielo, S. Gemma, A. Panico, M. Persico, B. Catalanotti, S. Ros, M. Brindisi, M. Agnusdei, I. Fiorini, V. Nacci, E. Novellino, T. Belinskaya, A. Saxena, and C. Fattorusso J. Med. Chem. 51 2008 3154
19. M. Decker, F. Krauth, and J. Lehmann Bioorg. Med. Chem. 14 2006 1966
20. M. Decker, B.S. Fulton, B. Zhang, B.I. Knapp, J.M. Bidlack, and J.M. Neumeyer J. Med. Chem. 52 2009 7389
21. M. Decker Eur. J. Med. Chem. 40 2005 305
22. M. Decker, B. Kraus, and J. Heilmann Bioorg. Med. Chem. 16 2008 4252
23. S. Petersen, and E. Tietze Liebigs Ann. Chem. 623 1959 166
24. S. Rannard, and N.J. Davis Org. Lett. 2 2000 2117
25. J.P. Colletier, B. Sanson, F. Nachon, E. Gabellieri, C. Fattorusso, G. Campiani, and M. Weik J. Am. Chem. Soc. 128 2006 2526
26. P.R. Carlier, E.S.-H. Chow, Y. Han, J. Liu, J. El Yazal, and Y.-P. Pang J. Med. Chem. 42 1999 4225
27. L. Savini, G. Campiani, A. Gaeta, C. Pellerano, C. Fattorusso, L. Chiasserini, J.M. Fedorko, and A. Saxena Bioorg. Med. Chem. Lett. 11 2001 1779
28. L. Savini, A. Gaeta, C. Fattorusso, B. Catalanotti, G. Campiani, L. Chiasserini, C. Pellerano, E. Novellino, D. McKissic, and A. Saxena J. Med. Chem. 46 2003 1
29. S. Senapati, J.M. Bui, and J.A. McCammon J. Med. Chem. 48 2005 8155
30. C.B. Millard, V.L. Shnyrov, S. Mewstead, I. Shin, E. Roth, I. Silman, and L. Weiner Protein Sci. 12 2003 2337
31. Y. Bourne, Z. Radic, G. Sulzenbacher, E. Kim, P. Taylor, and P. Marchot J. Biol. Chem. 281 2006 29256
32. J.M. Bui, K. Tai, and J.A. McCammon J. Am. Chem. Soc. 126 2004 7198
33. Molecular Operating Environment, version 2009.10; Chemical Computing Group, Inc.: Montreal, Quebec, Canada, 2009.
34. Schrödinger Suite 2008 Induced Fit Docking protocol; Glide version 5.0, Schrödinger, LLC, New York, NY, 2005; Prime version 1.7, Schrödinger, LLC, New York, NY, 2005.
35. LigPrep, version 2.2, Schrödinger, LLC, New York, NY, 2009.
36. Site Map, version 5, Schrödinger, LLC, New York, NY, 2009.