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,Azepine
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
MW : 529.27
Formula : C32H37N2O5
CAS_number :
PubChem : 23645164
UniChem : VFRNWNIHKJCFTE-BHRZLAGCSA-N
IUPHAR :
Wikipedia :
Target
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 : Greenblatt_2004_J.Am.Chem.Soc_126_15405 |
| ESTHER : Greenblatt_2004_J.Am.Chem.Soc_126_15405 |
| 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 : Mary_1998_Bioorg.Med.Chem_6_1835 |
| ESTHER : Mary_1998_Bioorg.Med.Chem_6_1835 |
| PubMedSearch : Mary_1998_Bioorg.Med.Chem_6_1835 |
| PubMedID: 9839013 |