CHEMBL4105611
the most potent inhibitor described in Kosak et al. 2016. IC50 hBCHE 4.9 +/- 0.3 nM and 0.4% residual activity at 10 microM; mouse ACHE 97% at 10 microM (IC50 10.2 nM hBChE)
General
Type : Piperidine, Sulfur Compound, Sulfonamide, PET probe, Naphthalen, Benzylpiperidine, Derivative of Donepezil
Chemical_Nomenclature : N-[(1-benzylpiperidin-3-yl)methyl]-N-(2-methoxyethyl)naphthalene-2-sulfonamide || N-{[(3S)-1-benzylpiperidin-3-yl]methyl}-N-(2-methoxyethyl)naphthalene-2-sulfonamide
Canonical SMILES : COCCN(CC1CCCN(C1)CC2=CC=CC=C2)S(=O)(=O)C3=CC4=CC=CC=C4C=C3 || COCCN(C[C@H]1CCCN(Cc2ccccc2)C1)S(=O)(=O)c1ccc2ccccc2c1
InChI : InChI=1S\/C26H32N2O3S\/c1-31-17-16-28(32(29,30)26-14-13-24-11-5-6-12-25(24)18-26)21-23-10-7-15-27(20-23)19-22-8-3-2-4-9-22\/h2-6,8-9,11-14,18,23H,7,10,15-17,19-21H2,1H3 || InChI=1S\/C26H32N2O3S\/c1-31-17-16-28(32(29,30)26-14-13-24-11-5-6-12-25(24)18-26)21-23-10-7-15-27(20-23)19-22-8-3-2-4-9-22\/h2-6,8-9,11-14,18,23H,7,10,15-17,19-21H2,1H3\/t23-\/m0\/s1
InChIKey : NIHBOOKOQZGYSF-UHFFFAOYSA-N || NIHBOOKOQZGYSF-QHCPKHFHSA-N
Other name(s) : 5DYW-5hf-C11 || [11C]BChE_OMe || (+\/-)[11C]N-((1-Benzylpiperidin-3-yl)methyl)-N-(2-methoxyethyl)naphthalene-2-sulfonamide || SCHEMBL18105284 || BDBM50246979 || SCHEMBL29521699 || A1JC3 || N-([(3S)-1-benzylpiperidin-3-yl]methyl)-N-(2-methoxyethyl)naphthalene-2-sulfonamide || N-([(3R)-1-benzylpiperidin-3-yl]methyl)-N-(2-methoxyethyl)naphthalene-2-sulfonamide || 5HF || 5DYW-5hf || ZINC000584904815 || Compound 2
MW : 452.6
Formula : C26H32N2O3S
CAS_number :
PubChem : 122581936, 123133730, 169297066, 163218517
UniChem : NIHBOOKOQZGYSF-UHFFFAOYSA-N, NIHBOOKOQZGYSF-QHCPKHFHSA-N
Target
Families : CHEMBL4105611 ligand of proteins in family
BCHE
Protein :
human-BCHE
References (6)
| Title : Lead Optimization of a Butyrylcholinesterase Inhibitor for the Treatment of Alzheimer's Disease - Kosak_2025_J.Med.Chem_68_11693 |
| Author(s) : Kosak U , Strasek Benedik N , Knez D , Zakelj S , Trontelj J , Pislar A , Horvat S , Bolje A , Znidarsic N , Grgurevic N , Svara T , Kljun J , Skrzypczak-Wiercioch A , Lv B , Xiong Y , Wang Q , Bian R , Shao J , Dias J , Nachon F , Brazzolotto X , Stojan J , Sun H , Salat K , Gobec S |
| Ref : Journal of Medicinal Chemistry , 68 :11693 , 2025 |
| Abstract : |
| PubMedSearch : Kosak_2025_J.Med.Chem_68_11693 |
| PubMedID: 40454648 |
| Gene_locus related to this paper: human-BCHE |
| Title : Chiral switch of a butyrylcholinesterase inhibitor for the treatment of Alzheimer's disease - Kosak_2025_Chem.Biol.Interact_15ChEPon_420_111670 |
| Author(s) : Kosak U , Knez D , Benetik SF , Sokolov PM , Pislar A , Horvat S , Stojan J , Lv B , Zhang W , Wang Y , Wang Q , Igert A , Dias J , Nachon F , Brazzolotto X , Sun H , Gobec S |
| Ref : Chemico-Biological Interactions , 420 :111670 , 2025 |
| Abstract : |
| PubMedSearch : Kosak_2025_Chem.Biol.Interact_15ChEPon_420_111670 |
| PubMedID: 40712769 |
| Gene_locus related to this paper: human-BCHE |
| Title : A novel butyrylcholinesterase inhibitor induces antidepressant, pro-cognitive, and anti-anhedonic effects in Flinders Sensitive Line rats: The role of the ghrelin-dopamine cascade - Olivier_2025_Biomed.Pharmacother_187_118093 |
| Author(s) : Olivier N , Harvey BH , Gobec S , Shahid M , Kosak U , Zakelj S , Brink CB |
| Ref : Biomed Pharmacother , 187 :118093 , 2025 |
| Abstract : |
| PubMedSearch : Olivier_2025_Biomed.Pharmacother_187_118093 |
| PubMedID: 40318448 |
| Title : Longitudinal evaluation of a novel BChE PET tracer as an early in vivo biomarker in the brain of a mouse model for Alzheimer disease - Rejc_2021_Theranostics_11_6542 |
| Author(s) : Rejc L , Gomez-Vallejo V , Joya A , Moreno O , Egimendia A , Castellnou P , Rios-Anglada X , Cossio U , Baz Z , Passannante R , Tobalina-Larrea I , Ramos-Cabrer P , Giralt A , Sastre M , Capetillo-Zarate E , Kosak U , Knez D , Gobec S , Marder M , Martin A , Llop J |
| Ref : Theranostics , 11 :6542 , 2021 |
| Abstract : |
| PubMedSearch : Rejc_2021_Theranostics_11_6542 |
| PubMedID: 33995675 |
| Title : Treatment of canine cognitive dysfunction with novel butyrylcholinesterase inhibitor - Zakosek Pipan_2021_Sci.Rep_11_18098 |
| Author(s) : Zakosek Pipan M , Prpar Mihevc S , Strbenc M , Kosak U , German Ilic I , Trontelj J , Zakelj S , Gobec S , Pavlin D , Majdic G |
| Ref : Sci Rep , 11 :18098 , 2021 |
| Abstract : |
| PubMedSearch : Zakosek Pipan_2021_Sci.Rep_11_18098 |
| PubMedID: 34518582 |
| Title : Development of an in-vivo active reversible butyrylcholinesterase inhibitor - Kosak_2016_Sci.Rep_6_39495 |
| Author(s) : Kosak U , Brus B , Knez D , Sink R , Zakelj S , Trontelj J , Pislar A , Slenc J , Gobec M , Zivin M , Tratnjek L , Perse M , Salat K , Podkowa A , Filipek B , Nachon F , Brazzolotto X , Wieckowska A , Malawska B , Stojan J , Rascan IM , Kos J , Coquelle N , Colletier JP , Gobec S |
| Ref : Sci Rep , 6 :39495 , 2016 |
| Abstract : |
| PubMedSearch : Kosak_2016_Sci.Rep_6_39495 |
| PubMedID: 28000737 |
| Gene_locus related to this paper: human-BCHE |