Methoxytacripyrine
enantiomer (S)-p-methoxytacripyrine is the most active. IC50 hACHE 0.045 microM hBCHE 100 microM. Able to interfere with the pro-aggregating action of hAChE, as a weak inhibitor of Abeta-1-42 self-aggregation, and a potent L-type Ca+2 antagonist (32.75 +/- 2.5% blockade in SH-SY5Y cells)
General
Type : Calcium Channel Antagonist, Derivative of Tacrine, Multitarget, anti-Abeta-aggregation
Chemical_Nomenclature : ethyl 5-amino-4-(4-methoxyphenyl)-2-methyl-1,4,6,7,8,9-hexahydrobenzo[b][1,8]naphthyridine-3-carboxylate
Canonical SMILES : CCOC(=O)C1=C(NC2=NC3=C(CCCC3)C(=C2C1C4=CC=C(C=C4)OC)N)C
InChI : InChI=1S\/C23H27N3O3\/c1-4-29-23(27)18-13(2)25-22-20(19(18)14-9-11-15(28-3)12-10-14)21(24)16-7-5-6-8-17(16)26-22\/h9-12,19H,4-8H2,1-3H3,(H3,24,25,26)
InChIKey : ZNRGREFWBCWZAU-UHFFFAOYSA-N
Other name(s) : SCHEMBL15026418 || (S)-p-methoxytacripyrine
MW : 393.5
Formula : C23H27N3O3
CAS_number :
PubChem : 16098498
UniChem : ZNRGREFWBCWZAU-UHFFFAOYSA-N
Target
Families : Methoxytacripyrine ligand of proteins in family
ACHE
Protein :
human-ACHE
References (5)
| Title : Chemical and pharmacological studies on enantiomerically pure p-methoxytacripyrines, promising multi-target-directed ligands for the treatment of Alzheimer's disease - |
| Author(s) : Bartolini M , Pistolozzi M , Andrisano V , Egea J , Lopez MG , Iriepa I , Moraleda I , Galvez E , Marco-Contelles J , Samadi A |
| Ref : ChemMedChem , 6 :1990 , 2011 |
| PubMedID: 21990269 |
| Title : Tacripyrines, the first tacrine-dihydropyridine hybrids, as multitarget-directed ligands for the treatment of Alzheimer's disease - Marco-Contelles_2009_J.Med.Chem_52_2724 |
| Author(s) : Marco-Contelles J , Leon R , de los Rios C , Samadi A , Bartolini M , Andrisano V , Huertas O , Barril X , Luque FJ , Rodriguez-Franco MI , Lopez B , Lopez MG , Garcia AG , Carreiras Mdo C , Villarroya M |
| Ref : Journal of Medicinal Chemistry , 52 :2724 , 2009 |
| Abstract : |
| PubMedSearch : Marco-Contelles_2009_J.Med.Chem_52_2724 |
| PubMedID: 19374444 |
| Title : New tacrine-dihydropyridine hybrids that inhibit acetylcholinesterase, calcium entry, and exhibit neuroprotection properties - Leon_2008_Bioorg.Med.Chem_16_7759 |
| Author(s) : Leon R , de los Rios C , Marco-Contelles J , Huertas O , Barril X , Luque FJ , Lopez MG , Garcia AG , Villarroya M |
| Ref : Bioorganic & Medicinal Chemistry , 16 :7759 , 2008 |
| Abstract : |
| PubMedSearch : Leon_2008_Bioorg.Med.Chem_16_7759 |
| PubMedID: 18640842 |
| Title : Multi-target-directed ligands to combat neurodegenerative diseases - |
| Author(s) : Cavalli A , Bolognesi ML , Minarini A , Rosini M , Tumiatti V , Recanatini M , Melchiorre C |
| Ref : Journal of Medicinal Chemistry , 51 :347 , 2008 |
| PubMedID: 18181565 |
| Title : Novel multipotent tacrine-dihydropyridine hybrids with improved acetylcholinesterase inhibitory and neuroprotective activities as potential drugs for the treatment of Alzheimer's disease - Marco-Contelles_2006_J.Med.Chem_49_7607 |
| Author(s) : Marco-Contelles J , Leon R , de los Rios C , Guglietta A , Terencio J , Lopez MG , Garcia AG , Villarroya M |
| Ref : Journal of Medicinal Chemistry , 49 :7607 , 2006 |
| Abstract : |
| PubMedSearch : Marco-Contelles_2006_J.Med.Chem_49_7607 |
| PubMedID: 17181144 |