Phthalimido-Galanthaminium-4d

IC50 0.1 +/- 0.02 (10-7 M) more potent than both Galanthamine and Tacrine (Mary et al 1998).Structure of torca-ACHE inhibited Greenblatt_2004 1W4L

General

Type : Derivative of Galanthamine, Alkaloid, Natural_modified, Alkyl linked bis-ligand, Isoindole, Phthalimido, Benzazepin, Azepine

Chemical_Nomenclature : 9-Deydro-10-N-Demethyl-10-N-(8'-phthalimidooctyl)-galanthaminium bromide

Canonical SMILES : COC1=C2C3=C(C=C1)C=[N+](CCC34C=CC(CC4O2)O)CCCCCCCCN5C(=O)C6=CC=CC=C6C5=O

InChI : InChI=1S\/C32H37N2O5\/c1-38-26-13-12-22-21-33(19-16-32-15-14-23(35)20-27(32)39-29(26)28(22)32)17-8-4-2-3-5-9-18-34-30(36)24-10-6-7-11-25(24)31(34)37\/h6-7,10-15,21,23,27,35H,2-5,8-9,16-20H2,1H3\/q+1\/t23-,27-,32-\/m0\/s1

InChIKey : VLGAHTYYCHWLNI-BHRZLAGCSA-N

Other name(s) : GL8  ||  Galanthamine derivative 3  ||  Galanthamine derivative  ||  CHEBI:609588  ||  CHEMBL490866  ||  BDBM10406  ||  (1S,12S,14R)-4-[8-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)octyl]-14-hydroxy-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-4,6,8,10(17),15-pentaen-4-ium  ||  (4AR,6S,8AR)-11-[8-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)octyl]-6-hydroxy-3-methoxy-5,6,9,10-tetrahydro-4AH-[1]benzofuro[3A,3,2-EF][2]benzazepin-11-ium


MW : 529.27

Formula : C32H37N2O5

CAS_number :

PubChem : 5288394

UniChem : VLGAHTYYCHWLNI-BHRZLAGCSA-N

Target

Families : Phthalimido-Galanthaminium-4d ligand of proteins in family
ACHE

Structure :
1W4L

Protein :
torca-ACHE

References (2)

Title : The complex of a bivalent derivative of galanthamine with torpedo acetylcholinesterase displays drastic deformation of the active-site gorge: implications for structure-based drug design - Greenblatt_2004_J.Am.Chem.Soc_126_15405
Author(s) : Greenblatt HM , Guillou C , Guenard D , Argaman A , Botti SA , Badet B , Thal C , Silman I , Sussman JL
Ref : Journal of the American Chemical Society , 126 :15405 , 2004
Abstract :
PubMedSearch : Greenblatt_2004_J.Am.Chem.Soc_126_15405
PubMedID: 15563167
Gene_locus related to this paper: torca-ACHE

Title : Potent acetylcholinesterase inhibitors: design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series - Mary_1998_Bioorg.Med.Chem_6_1835
Author(s) : Mary A , Renko DZ , Guillou C , Thal C
Ref : Bioorganic & Medicinal Chemistry , 6 :1835 , 1998
Abstract :
PubMedSearch : Mary_1998_Bioorg.Med.Chem_6_1835
PubMedID: 9839013