Tz2Pa6-anti1
The AChE inhibitor TZ2PA6 results from 1,3-dipolar cycloaddition (click chemistry) between a PAS inhibitor (phenylphenanthridinium) equipped with an acetylene group at the end of a flexible methylene chain and an active site inhibitor (tacrine)equipped with an azide group at the end of a methylene chain
General
Type : Acridine,Phenanthridinium,Derivative of Tacrine,Alkyl linked bis-ligand,Triazol
Chemical_Nomenclature : 3,8-Diamino-6-Phenyl-5-[6-[1-[2-[(1,2,3,4-tetrahydro-9-acridinyl)amino]ethyl]-1H-1,2,3-triazol-5-yl]hexyl] phenanthridinium
Canonical SMILES : C1=CC=C(C=C1)C2=C3C=C(C=CC3=C4C=CC(=CC4=[N+]2CCCCCCC5=CN(N=N5)CCNC6=C7C=CC=CC7=NC8=CC=CC=C86)N)N
InChI : InChI=1S\/C42H40N8\/c43-30-19-21-33-34-22-20-31(44)27-40(34)50(42(37(33)26-30)29-12-4-3-5-13-29)24-11-2-1-6-14-32-28-49(48-47-32)25-23-45-41-35-15-7-9-17-38(35)46-39-18-10-8-16-36(39)41\/h3-5,7-10,12-13,15-22,26-28,44H,1-2,6,11,14,23-25,43H2,(H,45,46)\/p+1
InChIKey : IIHWAURNXZAECF-UHFFFAOYSA-O
Other name(s) : CHEMBL117651
MW :
Formula : C42H45N8
CAS_number :
PubChem : 49786953
UniChem : IIHWAURNXZAECF-UHFFFAOYSA-O
IUPHAR :
Wikipedia :
Target
References (8)
| Title : Steric and Dynamic Parameters Influencing In Situ Cycloadditions to Form Triazole Inhibitors with Crystalline Acetylcholinesterase - Bourne_2016_J.Am.Chem.Soc_138_1611 |
| Author(s) : Bourne Y , Sharpless KB , Taylor P , Marchot P |
| Ref : Journal of the American Chemical Society , 138 :1611 , 2016 |
| Abstract : Bourne_2016_J.Am.Chem.Soc_138_1611 |
| ESTHER : Bourne_2016_J.Am.Chem.Soc_138_1611 |
| PubMedSearch : Bourne_2016_J.Am.Chem.Soc_138_1611 |
| PubMedID: 26731630 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : Conformational remodeling of femtomolar inhibitor-acetylcholinesterase complexes in the crystalline state - Bourne_2010_J.Am.Chem.Soc_132_18292 |
| Author(s) : Bourne Y , Radic Z , Taylor P , Marchot P |
| Ref : Journal of the American Chemical Society , 132 :18292 , 2010 |
| Abstract : Bourne_2010_J.Am.Chem.Soc_132_18292 |
| ESTHER : Bourne_2010_J.Am.Chem.Soc_132_18292 |
| PubMedSearch : Bourne_2010_J.Am.Chem.Soc_132_18292 |
| PubMedID: 21090615 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : Probing gorge dimensions of cholinesterases by freeze-frame click chemistry - Radic_2008_Chem.Biol.Interact_175_161 |
| Author(s) : Radic Z , Manetsch R , Fournier D , Sharpless KB , Taylor P |
| Ref : Chemico-Biological Interactions , 175 :161 , 2008 |
| Abstract : Radic_2008_Chem.Biol.Interact_175_161 |
| ESTHER : Radic_2008_Chem.Biol.Interact_175_161 |
| PubMedSearch : Radic_2008_Chem.Biol.Interact_175_161 |
| PubMedID: 18555981 |
| Title : Structural insights into conformational flexibility at the peripheral site and within the active center gorge of AChE - Bourne_2005_Chem.Biol.Interact_157-158_159 |
| Author(s) : Bourne Y , Radic Z , Kolb HC , Sharpless KB , Taylor P , Marchot P |
| Ref : Chemico-Biological Interactions , 157-158 :159 , 2005 |
| Abstract : Bourne_2005_Chem.Biol.Interact_157-158_159 |
| ESTHER : Bourne_2005_Chem.Biol.Interact_157-158_159 |
| PubMedSearch : Bourne_2005_Chem.Biol.Interact_157-158_159 |
| PubMedID: 16259971 |
| Title : Freeze-frame inhibitor captures acetylcholinesterase in a unique conformation - Bourne_2004_Proc.Natl.Acad.Sci.U.S.A_101_1449 |
| Author(s) : Bourne Y , Kolb HC , Radic Z , Sharpless KB , Taylor P , Marchot P |
| Ref : Proc Natl Acad Sci U S A , 101 :1449 , 2004 |
| Abstract : Bourne_2004_Proc.Natl.Acad.Sci.U.S.A_101_1449 |
| ESTHER : Bourne_2004_Proc.Natl.Acad.Sci.U.S.A_101_1449 |
| PubMedSearch : Bourne_2004_Proc.Natl.Acad.Sci.U.S.A_101_1449 |
| PubMedID: 14757816 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : In situ click chemistry: enzyme inhibitors made to their own specifications - Manetsch_2004_J.Am.Chem.Soc_126_12809 |
| Author(s) : Manetsch R , Krasinski A , Radic Z , Raushel J , Taylor P , Sharpless KB , Kolb HC |
| Ref : Journal of the American Chemical Society , 126 :12809 , 2004 |
| Abstract : Manetsch_2004_J.Am.Chem.Soc_126_12809 |
| ESTHER : Manetsch_2004_J.Am.Chem.Soc_126_12809 |
| PubMedSearch : Manetsch_2004_J.Am.Chem.Soc_126_12809 |
| PubMedID: 15469276 |
| Title : Cover picture: angew. Chem. Int. Ed. 6\/2002 - Lewis_2002_Angew.Chem.Int.Ed.Engl_41_875 |
| Author(s) : Lewis WG , Green LG , Grynszpan F , Radic Z , Carlier PR , Taylor P , Finn MG , Sharpless KB |
| Ref : Angew Chem Int Ed Engl , 41 :875 , 2002 |
| Abstract : Lewis_2002_Angew.Chem.Int.Ed.Engl_41_875 |
| ESTHER : Lewis_2002_Angew.Chem.Int.Ed.Engl_41_875 |
| PubMedSearch : Lewis_2002_Angew.Chem.Int.Ed.Engl_41_875 |
| PubMedID: |
| Title : Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks - |
| Author(s) : Lewis WG , Green LG , Grynszpan F , Radic Z , Carlier PR , Taylor P , Finn MG , Sharpless KB |
| Ref : Angew Chem Int Ed Engl , 41 :1053 , 2002 |
| PubMedID: 12491310 |