Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/springer-journals/automated-docking-of-82-n-benzylpiperidine-derivatives-to-mouse-D47iJ4sp6w
References (48)
-
M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, J.J.P. Stewart (1985)
J. Am. Chem. Soc., 107
-
J.L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, I. Silman (1991)
Science, 253
-
Y. Yamamoto (1994)
Docking Analysis of a Series of Benzylamino Acetylcholinesterase Inhibitors with a Phthalimide, Benzoyl, or Indanone MoietyJ. Med. Chem., 37
-
R.D. Cramer, J.D. Bunce, D.E. Patterson, I.E. Frank (1988)
Quant. Struct.-Act. Relat., 7
-
E. I. Barnard (1974)
The Peripheral Nervous System -
Y. Ishihara (1991)
Central Cholinergic Agents. I. Potent Acethlcholinesterase Inhibitors, 2-(.OMEGA.-(N-Alkyl-N-(.OMEGA.-phenyl-alkyl)amino)alkyl)-1H-isoindole-1,3(2H)-diones, Based on a New Hypothesis of the Enzyme's Active Site.Chem. Pharm. Bull., 39
-
R.D. Cramer III (1988)
Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteinsJ. Am. Chem. Soc., 110
-
A. Inoue (1996)
The Simulated Binding of (±)-2,3-Dihydro-5,6-dimethoxy-2-[[1-(phenylmethyl)-4- piperidinyl]methyl]-1H-inden-1-one Hydrochloride (E2020) and Related Inhibitors to Free and Acylated Acetylcholinesterases and Corresponding Structure−Activity AnalysesJ. Med. Chem., 39
-
Y. Ishihara, K. Kato, G. Goto (1991)
Chem. Pharm. Bull., 39
-
Z. Radic, N.A. Pickering, D.C. Vellom, S. Camp, P. Taylor (1993)
Biochemistry, 32
-
N.R. Sims, D.M. Bowen, S.J. Allen, C.C.T. Smith, D. Neary, D.J. Thomas, A.N. Davison (1983)
J. Neurochem., 40
-
C.A. Johns, V. Haroutunian, B.S. Greenwald, R.C. Mohs, B.M. Davis, P. Kanof, T.B. Horvath, K.L. Davis (1985)
Drug. Dev. Res., 5
-
H. Sugimoto (1990)
Novel piperidine derivatives. Synthesis and anti-acetylcholinesterase activity of 1-benzyl-4-[2-(N-benzoylamino)ethyl]piperidine derivativesJ. Med. Chem., 33
-
W. Tong (1996)
A Comparative Molecular Field Analysis Study ofN-Benzylpiperidines as Acetylcholinesterase InhibitorsJ. Med. Chem., 39
-
S.J. Weiner (1986)
An all atom force field for simulations of proteins and nucleic acidsJ. Comput. Chem., 7
-
M.G. Cardozo (1992)
Quantitative structure-activity relationship. QSAR, analyses of the substituted indanone and benzylpiperidine rings of a series of indanone-benzylpiperidine inhibitors of acetylcholinesteraseJ. Med. Chem., 35
-
D.M. Fink (1995)
Synthesis and Evaluation of 5-Amino-5,6,7,8-tetrahydroquinolinones as Potential Agents for the Treatment of Alzheimer's DiseaseJ. Med. Chem., 38
-
A. Ordentlich (1993)
Dissection of the human acetylcholinesterase active center determinants of substrate specificity. Identification of residues constituting the anionic site, the hydrophobic site, and the acyl pocketJ. Biol. Chem., 268
-
V. John (1993)
Annu. Rep. Med. Chem., 28
-
C.L. Waller (1993)
Three-dimensional QSAR of human immunodeficiency virus (I) protease inhibitors. 1. A CoMFA study employing experimentally-determined alignment rulesJ. Med. Chem., 36
-
I.D. Kuntz, E.C. Meng, B.K. Shoichet (1994)
Acc. Chem. Res., 27
-
Z. Radic (1993)
Three distinct domains in the cholinesterase molecule confer selectivity for acetyl- and butyrylcholinesterase inhibitorsBiochemistry, 32
-
N.R. Sims (1983)
Presynaptic Cholinergic Dysfunction in Patients with DementiaJ. Neurochem., 40
-
S.J. Cho (1996)
Structure-Based Alignment and Comparative Molecular Field Analysis of Acetylcholinesterase InhibitorsJ. Med. Chem., 39
-
A. Villalobos (1994)
Novel Benzisoxazole Derivatives as Potent and Selective Inhibitors of AcetylcholinesteraseJ. Med. Chem., 37
-
E. I. Barnard (1974)
Neuromuscular Transmission—Enzymatic Destruction of Acetylcholine -
M. Clarc (1989)
Validation of the general purpose tripos 5.2 force fieldJ. Comput. Chem., 10
-
M. Harel, I. Schalk, L. Ehret-Sabatier, F. Bouet, M. Goeldner, C. Hirth, P. Axelsen, I. Silman, J. L. Sussman (1993)
Proc. Natl. Acad. Sci. USA, 90
-
D.M. Fink, G.M. Bores, R.C. Effland, F.P. Huger, B.E. Kurys, D.K. Rush, D.E. Selk (1995)
J. Med. Chem., 38
-
M.B. Brennan (1997)
Chem. Eng. News, 20
-
J.L. Sussman (1991)
Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding proteinScience, 253
-
A. Villalobos (1995)
5,7-Dihydro-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-6H-pyrrolo[3,2-f]-1,2-benzisoxazol-6-one: A Potent and Centrally-Selective Inhibitor of AcetylcholinesteraseJ. Med. Chem., 38
-
Y.-P. Pang, A.P. Kozikowski (1994)
J. Comput.-Aided Mol. Design, 8
-
R.D. Cramer (1988)
Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR StudiesQuant. Struct.-Act. Relat., 7
-
A. Ordentlich, D. Barak, C. Kronman, Y. Flashner, M. Leitner, Y. Segal, N. Ariel, S. Cohen, B. Velan, A. Shafferman (1993)
J. Biol. Chem., 268
-
M.J.S. Dewar (1985)
Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular modelJ. Am. Chem. Soc., 107
-
D.A. Dougherty (1996)
Cation-pi Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and TrpScience, 271
-
Y.-P. Pang (1994)
Prediction of the binding site of 1-benzyl-4-[(5,6-dimethoxy-1-indanon-2-yl)methyl]piperidine in acetylcholinesterase by docking studies with the SYSDOC programJ. Comput.-Aided Mol. Design, 8
-
M.N. Rosser, L.L. Iversen, G.P. Reynolds, C.A. Mountjoy, M. Roth (1984)
Br. Med. J., 288
-
E.K. Perry (1986)
Br. Med. Bull., 42
-
R.E. Becker (1988)
Mechanisms of cholinesterase inhibition in senile dementia of the alzheimer type: Clinical, pharmacological, and therapeutic aspectsDrug Dev. Res., 12
-
M. Harel (1993)
Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase.Proc. Natl. Acad. Sci. USA, 90
-
S. Clementi, S. Wold (1995)
Chemometric Methods in Drug Design -
M. Clarc, R.D. Cramer, N. Van Opdenbosch (1989)
J. Comput. Chem., 10
-
I.D. Kuntz (1994)
Structure-Based Molecular DesignAcc. Chem. Res., 27
-
H. Sugimoto (1992)
Synthesis and structure-activity relationships of acetylcholinesterase inhibitors: 1-benzyl-4-(2-phthalimidoethyl)piperidine, and related derivativesJ. Med. Chem., 35
-
C.A. Johns (1985)
Development of cholinergic drugs for the treatment of Alzheimer's diseaseDrug. Dev. Res., 5
-
M.N. Rosser (1984)
Neurochemical characteristics of early and late onset types of Alzheimer's disease.Br. Med. J., 288
- Publisher
- Springer Journals
- Copyright
- Copyright © 1999 by Kluwer Academic Publishers
- Subject
- Chemistry; Computer Applications in Chemistry; Physical Chemistry; Animal Anatomy / Morphology / Histology
- ISSN
- 0920-654X
- eISSN
- 1573-4951
- DOI
- 10.1023/A:1008071118697
- Publisher site
- See Article on Publisher Site
Abstract
Automated docking and three-dimensional Quantitative Structure-Activity Relationship studies (3D QSAR) were performed for a series of 82 reversible, competitive and selective acetylcholinesterase (AChE) inhibitors. The suggested automated docking technique, making use of constraints taken from experimental crystallographic data, allowed to dock all the 82 substituted N-benzylpiperidines to the crystal structure of mouse AChE, because of short computational times. A 3D QSAR model was then established using the CoMFA method. In contrast to conventional CoMFA studies, the compounds were not fitted to a reference molecule but taken in their 'natural' alignment obtained by the docking study. The established and validated CoMFA model was then applied to another series of 29 N-benzylpiperidine derivatives whose AChE inhibitory activity data were measured under different experimental conditions. A good correlation between predicted and experimental activity data shows that the model can be extended to AChE inhibitory activity data measured on another acetylcholinesterase and/or at different incubation times and pH level.
Journal
Journal of Computer-Aided Molecular Design – Springer Journals
Published: Sep 30, 2004