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Literature summary for 3.1.1.7 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
Search for more literature for 3.1.1.7

Application

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

Inhibitors

Inhibitors Comment Organism Structure
1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Electrophorus electricus
1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Electrophorus electricus
1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Electrophorus electricus
1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Electrophorus electricus
1-benzyl-N-[3-(2,3-dihydro-1H-indol-1-yl)propyl]piperidin-4-amine
-
 Electrophorus electricus
1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
-
 Electrophorus electricus
1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
-
 Electrophorus electricus
1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
-
 Electrophorus electricus
2-(3-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(3-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(3-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(3-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]propyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(6-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(6-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(6-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(6-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]hexyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(8-[[1-(2-fluorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(8-[[1-(3-chlorobenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(8-[[1-(4-hydroxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-(8-[[1-(4-methoxybenzyl)piperidin-4-yl]amino]octyl)-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
-
 Electrophorus electricus
4-[(4-[[6-(1H-indol-1-yl)hexyl]amino]piperidin-1-yl)methyl]phenol
-
 Electrophorus electricus
4-[(4-[[8-(1H-indol-1-yl)octyl]amino]piperidin-1-yl)methyl]phenol
-
 Electrophorus electricus
donepezil
-
 Electrophorus electricus
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
N-[6-(1H-indol-1-yl)hexyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Electrophorus electricus
N-[8-(1H-indol-1-yl)octyl]-1-(4-methoxybenzyl)piperidin-4-amine
-
 Electrophorus electricus
tacrine
-
 Electrophorus electricus

Organism

Organism UniProt Comment Textmining
Electrophorus electricus O42275
-
-

Source Tissue

Source Tissue Comment Organism Textmining
commercial preparation
-
 Electrophorus electricus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
acetylthiocholine + H2O
-
 Electrophorus electricus thiocholine + acetate
-
 ?

Synonyms

Synonyms Comment Organism
AChE
-
 Electrophorus electricus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Electrophorus electricus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Electrophorus electricus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
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
0.00811
-
 pH 8.0, 25°C Electrophorus electricus 2-[3-[(1-benzylpiperidin-4-yl)amino]propyl]-1H-isoindole-1,3(2H)-dione
0.01767
-
 pH 8.0, 25°C Electrophorus electricus 2-[8-[(1-benzylpiperidin-4-yl)amino]octyl]-1H-isoindole-1,3(2H)-dione
0.02168
-
 pH 8.0, 25°C Electrophorus electricus 1-(2-fluorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
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
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
0.0261
-
 pH 8.0, 25°C Electrophorus electricus 1-(3-chlorobenzyl)-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
0.02961
-
 pH 8.0, 25°C Electrophorus electricus 1-benzyl-N-[8-(1H-indol-1-yl)octyl]piperidin-4-amine
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
0.042
-
 pH 8.0, 25°C Electrophorus electricus 1-benzyl-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
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
0.04536
-
 pH 8.0, 25°C Electrophorus electricus 2-[6-[(1-benzylpiperidin-4-yl)amino]hexyl]-1H-isoindole-1,3(2H)-dione
0.04741
-
 pH 8.0, 25°C Electrophorus electricus 1-(3-chlorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
0.05322
-
 pH 8.0, 25°C Electrophorus electricus 1-(2-fluorobenzyl)-N-[6-(1H-indol-1-yl)hexyl]piperidin-4-amine
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
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
0.06903
-
 pH 8.0, 25°C Electrophorus electricus 2-[5-[(1-benzylpiperidin-4-yl)amino]pentyl]-1H-isoindole-1,3(2H)-dione
0.07011
-
 pH 8.0, 25°C Electrophorus electricus 1-benzyl-N-[5-(2,3-dihydro-1H-indol-1-yl)pentyl]piperidin-4-amine
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
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