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Inhibitor Report for: Phthalimido-Galanthaminium-8d

IC50 0.7 +/- 0.1 (10-7 M) Comparable to Tacrine , more potent than Galanthamine (Mary et al.1998).Structure of torca-ACHE inhibited Greenblatt_2004 1W76


General
Type Derivative of Galanthamine, Alkaloid, Natural_modified, Alkyl linked bis-ligand, Isoindole, Indole, Phthalimido, Benzazepin
Chemical_Nomenclature 2-[8-[[(1S,12S,14R)-14-hydroxy-4-methyl-11-oxa-4-azoniatetracyclo[8.6.1.01,12.06,17]heptadeca-4,6(17),7,9,15-pentaen-9-yl]oxy]octyl]isoindole-1,3-dione
Canonical SMILES C[N+]1=CC2=C3C(=C(C=C2)OCCCCCCCCN4C(=O)C5=CC=CC=C5C4=O)OC6C3(CC1)C=CC(C6)O
InChI InChI=1S/C32H37N2O5/c1-33-18-16-32-15-14-23(35)20-27(32)39-29-26(13-12-22(21-33)28(29)32)38-19-9-5-3-2-4-8-17-34-30(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 VFRNWNIHKJCFTE-BHRZLAGCSA-N
Other name(s) 9-Deydro-6-O-Demethyl-6-O-(8'-phthalimidooctyl)-galanthaminium bromide ; Galanthamine deriv. 8d ; Galanthamine derivative 4 ; BDBM10407 ; (1S,12S,14R)-9-{[8-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)octyl]oxy}-14-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-4,6,8,10(17),15-pentaen-4-ium ; (4aS,8aS)-3-[[8-(1,3-Dioxo-1,3-dihydro-2H-isoindole-2-yl)octyl]oxy]-6beta-hydroxy-11-methyl-4aalpha,5,9,10-tetrahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine-11-ium
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MW|529.27
Formula|C32H37N2O5
CAS_number|
PubChem|23645164
UniChem|VFRNWNIHKJCFTE-BHRZLAGCSA-N
IUPHAR|
Wikipedia|

Target
Families | Phthalimido-Galanthaminium-8d ligand of proteins in family: ACHE

References:
Search PubMed for references concerning: Phthalimido-Galanthaminium-8d
    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 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 : PubMed

            

    Title: Potent acetylcholinesterase inhibitors: design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series
    Mary A, Renko DZ, Guillou C, Thal C
    Ref: Bioorganic & Medicinal Chemistry, 6:1835, 1998 : PubMed