Tetracyclic-carbamate-photoswitch-azo

In vitro 10-fold difference in the IC50-values (44.6 nM cis, 424 nM trans). In vivo all or nothing response with complete recovery in a murine cognition-deficit AD model at dosages as low as 0.3 mg/kg. 54.9% inhibition AChE at 15microM, IC 50 hBChE 0.0446 micro M

General

Type : Carbamate, Natural_modified, Derivative of Evodiamine, Isoquinoline, Quinazoline, Photoswitch

Chemical_Nomenclature : (13-methyl-2-phenyldiazenyl-5,6,8,13a-tetrahydroisoquinolino[1,2-b]quinazolin-10-yl) N-heptylcarbamate

Canonical SMILES : CCCCCCCNC(=O)OC1=CC2=C(C=C1)N(C3C4=C(CCN3C2)C=CC(=C4)N=NC5=CC=CC=C5)C

InChI : InChI=1S\/C31H37N5O2\/c1-3-4-5-6-10-18-32-31(37)38-27-15-16-29-24(20-27)22-36-19-17-23-13-14-26(21-28(23)30(36)35(29)2)34-33-25-11-8-7-9-12-25\/h7-9,11-16,20-21,30H,3-6,10,17-19,22H2,1-2H3,(H,32,37)

InChIKey : YYFAPCBCSCQDFB-UHFFFAOYSA-N

Other name(s) : CHEMBL5220673  ||  BDBM50606789  ||  Cpd 15-cis


MW : 511.7g\/mol

Formula : C31H37N5O2

CAS_number :

PubChem : 164675714

UniChem : YYFAPCBCSCQDFB-UHFFFAOYSA-N

Target

Families : Tetracyclic-carbamate-photoswitch-azo ligand of proteins in family
BCHE

Protein :
human-BCHE

References (1)

Title : Photoswitchable Pseudoirreversible Butyrylcholinesterase Inhibitors Allow Optical Control of Inhibition in Vitro and Enable Restoration of Cognition in an Alzheimer's Disease Mouse Model upon Irradiation - Scheiner_2022_J.Am.Chem.Soc__
Author(s) : Scheiner M , Sink A , Hoffmann M , Vrigneau C , Endres E , Carles A , Sotriffer C , Maurice T , Decker M
Ref : Journal of the American Chemical Society , : , 2022
Abstract :
PubMedSearch : Scheiner_2022_J.Am.Chem.Soc__
PubMedID: 35138833