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Literature summary extracted from

  • Wieckowska, A.; Wieckowski, K.; Bajda, M.; Brus, B.; Salat, K.; Czerwinska, P.; Gobec, S.; Filipek, B.; Malawska, B.
    Synthesis of new N-benzylpiperidine derivatives as cholinesterase inhibitors with beta-amyloid anti-aggregation properties and beneficial effects on memory in vivo (2015), Bioorg. Med. Chem., 23, 2445-2457 .
    View publication on PubMed

Application

EC Number Application Comment Organism
3.1.1.7 drug development acetylcholinesterase, butyrylcholinesterase and beta-amyloid are the predominant biological targets in the search for anti-Alzheimer's agents Electrophorus electricus
3.1.1.8 drug development acetylcholinesterase, butyrylcholinesterase and beta-amyloid are the predominant biological targets in the search for anti-Alzheimer's agents Equus caballus

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.1.7 1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 1-benzyl-N-[3-(2,3-dihydro-1H-indol-1-yl)propyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 2-(3-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(3-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(3-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(3-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(6-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(6-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(6-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(6-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(8-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(8-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(8-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-(8-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
3.1.1.7 4-[(4-[[6-(1H-indol-1-yl)hexyl]amino]piperidin-1-yl)methyl]phenol
-
 Electrophorus electricus
3.1.1.7 4-[(4-[[8-(1H-indol-1-yl)octyl]amino]piperidin-1-yl)methyl]phenol
-
 Electrophorus electricus
3.1.1.7 donepezil
-
 Electrophorus electricus
3.1.1.7 additional information evaluation of a combination of both anticholinesterase and beta-amyloid anti-aggregation activities in one molecule, and therapeutic potential in vivo. Design and synthesis of 28 compounds as derivatives of donepezil that contain the N-benzylpiperidine moiety combined with the phthalimide or indole moieties. No or poor inhibition by 23, 27, 28, 30, 38, 39, 40, and 41 Electrophorus electricus
3.1.1.7 N-[6-(1H-indol-1-yl)hexyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 N-[8-(1H-indol-1-yl)octyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Electrophorus electricus
3.1.1.7 tacrine
-
 Electrophorus electricus
3.1.1.8 1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 1-benzyl-N-[3-(2,3-dihydro-1H-indol-1-yl)propyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Equus caballus
3.1.1.8 2-(3-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(3-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(3-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(3-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(6-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(6-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(6-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(6-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(8-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(8-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione a selective BChE inhibitor Equus caballus
3.1.1.8 2-(8-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-(8-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
-
 Equus caballus
3.1.1.8 4-[(4-[[6-(1H-indol-1-yl)hexyl]amino]piperidin-1-yl)methyl]phenol
-
 Equus caballus
3.1.1.8 4-[(4-[[8-(1H-indol-1-yl)octyl]amino]piperidin-1-yl)methyl]phenol
-
 Equus caballus
3.1.1.8 donepezil
-
 Equus caballus
3.1.1.8 additional information evaluation of a combination of both anticholinesterase and beta-amyloid anti-aggregation activities in one molecule, and therapeutic potential in vivo. Design and synthesis of 28 compounds as derivatives of donepezil that contain the N-benzylpiperidine moiety combined with the phthalimide or indole moieties. No or poor inhibition by 2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione Equus caballus
3.1.1.8 N-[6-(1H-indol-1-yl)hexyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Equus caballus
3.1.1.8 N-[8-(1H-indol-1-yl)octyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Equus caballus
3.1.1.8 tacrine
-
 Equus caballus

Organism

EC Number Organism UniProt Comment Textmining
3.1.1.7 Electrophorus electricus O42275
-
-
3.1.1.8 Equus caballus P81908
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.1.1.7 commercial preparation
-
 Electrophorus electricus
-
3.1.1.8 commercial preparation
-
 Equus caballus
-
3.1.1.8 serum
-
 Equus caballus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.1.7 acetylthiocholine + H2O
-
 Electrophorus electricus thiocholine + acetate
-
 ?
3.1.1.8 butyrylthiocholine + H2O
-
 Equus caballus thiocholine + butyrate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.1.1.7 AChE
-
 Electrophorus electricus
3.1.1.8 butyrylcholinesterase
-
 Equus caballus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.1.1.7 25
-
 assay at Electrophorus electricus
3.1.1.8 25
-
 assay at Equus caballus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.1.1.7 8
-
 assay at Electrophorus electricus
3.1.1.8 8
-
 assay at Equus caballus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.1.1.7 0.00452
-
 pH 8.0, 25°C Electrophorus electricus 2-(3-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.00811
-
 pH 8.0, 25°C Electrophorus electricus 2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.01767
-
 pH 8.0, 25°C Electrophorus electricus 2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.02168
-
 pH 8.0, 25°C Electrophorus electricus 1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
3.1.1.7 0.02308
-
 pH 8.0, 25°C Electrophorus electricus 2-(3-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.02354
-
 pH 8.0, 25°C Electrophorus electricus 2-(8-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.0261
-
 pH 8.0, 25°C Electrophorus electricus 1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
3.1.1.7 0.02961
-
 pH 8.0, 25°C Electrophorus electricus 1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
3.1.1.7 0.02977
-
 pH 8.0, 25°C Electrophorus electricus 2-(6-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.042
-
 pH 8.0, 25°C Electrophorus electricus 1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
3.1.1.7 0.04339
-
 pH 8.0, 25°C Electrophorus electricus 2-(8-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.04536
-
 pH 8.0, 25°C Electrophorus electricus 2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.04741
-
 pH 8.0, 25°C Electrophorus electricus 1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
3.1.1.7 0.05322
-
 pH 8.0, 25°C Electrophorus electricus 1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
3.1.1.7 0.05441
-
 pH 8.0, 25°C Electrophorus electricus 2-(6-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.06833
-
 pH 8.0, 25°C Electrophorus electricus 2-(3-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.06903
-
 pH 8.0, 25°C Electrophorus electricus 2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione
3.1.1.7 0.07011
-
 pH 8.0, 25°C Electrophorus electricus 1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
3.1.1.7 0.0853
-
 pH 8.0, 25°C Electrophorus electricus 2-(6-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
3.1.1.7 43.34
-
 pH 8.0, 25°C Electrophorus electricus 2-(8-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00034
-
 pH 8.0, 25°C Equus caballus 4-[(4-[[8-(1H-indol-1-yl)octyl]amino]piperidin-1-yl)methyl]phenol
3.1.1.8 0.00052
-
 pH 8.0, 25°C Equus caballus 4-[(4-[[6-(1H-indol-1-yl)hexyl]amino]piperidin-1-yl)methyl]phenol
3.1.1.8 0.00072
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00075
-
 pH 8.0, 25°C Equus caballus 1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
3.1.1.8 0.00081
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00083
-
 pH 8.0, 25°C Equus caballus 1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
3.1.1.8 0.00093
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
3.1.1.8 0.00108
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
3.1.1.8 0.00133
-
 pH 8.0, 25°C Equus caballus 1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
3.1.1.8 0.00178
-
 pH 8.0, 25°C Equus caballus 1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
3.1.1.8 0.00187
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00198
-
 pH 8.0, 25°C Equus caballus 2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00232
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00273
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00341
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
3.1.1.8 0.004
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00446
-
 pH 8.0, 25°C Equus caballus N-[8-(1H-indol-1-yl)octyl]-1-(4-methoxybenzyl)piperidin-4-amine
3.1.1.8 0.00453
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00565
-
 pH 8.0, 25°C Equus caballus 2-(8-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00739
-
 pH 8.0, 25°C Equus caballus 2-(6-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.00813
-
 pH 8.0, 25°C Equus caballus N-[6-(1H-indol-1-yl)hexyl]-1-(4-methoxybenzyl)piperidin-4-amine
3.1.1.8 0.00937
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.01052
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.01285
-
 pH 8.0, 25°C Equus caballus 2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.0153
-
 pH 8.0, 25°C Equus caballus 1-benzyl-N-[3-(2,3-dihydro-1H-indol-1-yl)propyl]piperidin-4-amine
3.1.1.8 0.0268
-
 pH 8.0, 25°C Equus caballus 2-(3-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
3.1.1.8 0.0518
-
 pH 8.0, 25°C Equus caballus 2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione