C-547
derivative of 6-methyluracil
General
Type : Bisquaternary,Pyrimidine,Uracil derivative
Chemical_Nomenclature : 5-[3-[5-[diethyl-[(2-nitrophenyl)methyl]azaniumyl]pentyl]-4-methyl-2,6-dioxopyrimidin-1-yl]pentyl-diethyl-[(2-nitrophenyl)methyl]azanium
Canonical SMILES : CC[N+](CC)(CCCCCN1C(=CC(=O)N(C1=O)CCCCC[N+](CC)(CC)CC2=CC=CC=C2[N+](=O)[O-])C)CC3=CC=CC=C3[N+](=O)[O-]
InChI : InChI=1S\/C37H56N6O6\/c1-6-42(7-2,29-32-20-12-14-22-34(32)40(46)47)26-18-10-16-24-38-31(5)28-36(44)39(37(38)45)25-17-11-19-27-43(8-3,9-4)30-33-21-13-15-23-35(33)41(48)49\/h12-15,20-23,28H,6-11,16-19,24-27,29-30H2,1-5H3\/q+2
InChIKey : WLTAFWKKNBLBHO-UHFFFAOYSA-N
Other name(s) : 1,3-bis[5(dietyl-o-nitro-benzylammonio)pentyl]-6-metylura,1,3-Bis[5-(diethyl 2-nitrobenzylaminio)pentyl]-6-methylpyrimidine-2,4-dione,C547,G0W
MW : 680.87
Formula : C37H56N6O6
CAS_number :
PubChem : 10372410
UniChem : WLTAFWKKNBLBHO-UHFFFAOYSA-N
IUPHAR :
Wikipedia :
Target
Families : C-547 ligand of proteins in family: ACHE
Stucture : 5FKJ Crystal structure of mouse acetylcholinesterase in complex with C-547, an alkyl ammonium derivative of 6-methyl uracil
Protein : mouse-ACHE
References (11)
| Title : Slow-binding reversible inhibitor of acetylcholinesterase with long-lasting action for prophylaxis of organophosphate poisoning - Lenina_2020_Sci.Rep_10_16611 |
| Author(s) : Lenina OA , Zueva IV , Zobov VV , Semenov VE , Masson P , Petrov KA |
| Ref : Sci Rep , 10 :16611 , 2020 |
| Abstract : Lenina_2020_Sci.Rep_10_16611 |
| ESTHER : Lenina_2020_Sci.Rep_10_16611 |
| PubMedSearch : Lenina_2020_Sci.Rep_10_16611 |
| PubMedID: 33024231 |
| Title : C-547, a 6-methyluracil derivative with long-lasting binding and rebinding on acetylcholinesterase: Pharmacokinetic and pharmacodynamic studies - Petrov_2018_Neuropharmacol_131_304 |
| Author(s) : Petrov KA , Zueva IV , Kovyazina IV , Sedov I , Lushchekina SV , Kharlamova AD , Lenina O , Koshkin S , Shtyrlin Y , Nikolsky EE , Masson P |
| Ref : Neuropharmacology , 131 :304 , 2018 |
| Abstract : Petrov_2018_Neuropharmacol_131_304 |
| ESTHER : Petrov_2018_Neuropharmacol_131_304 |
| PubMedSearch : Petrov_2018_Neuropharmacol_131_304 |
| PubMedID: 29277489 |
| Title : Slow-binding inhibition of acetylcholinesterase by an alkylammonium derivative of 6-methyluracil: mechanism and possible advantages for myasthenia gravis treatment - Kharlamova_2016_Biochem.J_473_1225 |
| Author(s) : Kharlamova AD , Lushchekina SV , Petrov KA , Kots ED , Nachon F , Villard-Wandhammer M , Zueva IV , Krejci E , Reznik VS , Zobov VV , Nikolsky EE , Masson P |
| Ref : Biochemical Journal , 473 :1225 , 2016 |
| Abstract : Kharlamova_2016_Biochem.J_473_1225 |
| ESTHER : Kharlamova_2016_Biochem.J_473_1225 |
| PubMedSearch : Kharlamova_2016_Biochem.J_473_1225 |
| PubMedID: 26929400 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : 6-Methyluracil Derivatives as Bifunctional Acetylcholinesterase Inhibitors for the Treatment of Alzheimer's Disease - Semenov_2015_ChemMedChem_10_1863 |
| Author(s) : Semenov VE , Zueva IV , Mukhamedyarov MA , Lushchekina SV , Kharlamova AD , Petukhova EO , Mikhailov AS , Podyachev SN , Saifina LF , Petrov KA , Minnekhanova OA , Zobov VV , Nikolsky EE , Masson P , Reznik VS |
| Ref : ChemMedChem , 10 :1863 , 2015 |
| Abstract : Semenov_2015_ChemMedChem_10_1863 |
| ESTHER : Semenov_2015_ChemMedChem_10_1863 |
| PubMedSearch : Semenov_2015_ChemMedChem_10_1863 |
| PubMedID: 26412714 |
| Title : Effect of tissue-specific acetylcholinesterase inhibitor C-547 on alpha3beta4 and alphabetaepsilondelta acetylcholine receptors in COS cells - Lindovsky_2012_Eur.J.Pharmacol_688_22 |
| Author(s) : Lindovsky J , Petrov KA , Krusek J , Reznik VS , Nikolsky EE , Vyskocil F |
| Ref : European Journal of Pharmacology , 688 :22 , 2012 |
| Abstract : Lindovsky_2012_Eur.J.Pharmacol_688_22 |
| ESTHER : Lindovsky_2012_Eur.J.Pharmacol_688_22 |
| PubMedSearch : Lindovsky_2012_Eur.J.Pharmacol_688_22 |
| PubMedID: 22634638 |
| Title : Different sensitivities of rat skeletal muscles and brain to novel anti-cholinesterase agents, alkylammonium derivatives of 6-methyluracil (ADEMS) - Petrov_2011_Br.J.Pharmacol_163_732 |
| Author(s) : Petrov KA , Yagodina LO , Valeeva GR , Lannik NI , Nikitashina AD , Rizvanov AA , Zobov VV , Bukharaeva EA , Reznik VS , Nikolsky EE , Vyskocil F |
| Ref : British Journal of Pharmacology , 163 :732 , 2011 |
| Abstract : Petrov_2011_Br.J.Pharmacol_163_732 |
| ESTHER : Petrov_2011_Br.J.Pharmacol_163_732 |
| PubMedSearch : Petrov_2011_Br.J.Pharmacol_163_732 |
| PubMedID: 21232040 |
| Title : Mechanisms of cardiac muscle insensitivity to a novel acetylcholinesterase inhibitor C-547 - Abramochkin_2009_J.Cardiovasc.Pharmacol_53_162 |
| Author(s) : Abramochkin DV , Petrov KA , Zobov VV , Yagodina LO , Nikolsky EE , Rosenshtraukh LV |
| Ref : J Cardiovasc Pharmacol , 53 :162 , 2009 |
| Abstract : Abramochkin_2009_J.Cardiovasc.Pharmacol_53_162 |
| ESTHER : Abramochkin_2009_J.Cardiovasc.Pharmacol_53_162 |
| PubMedSearch : Abramochkin_2009_J.Cardiovasc.Pharmacol_53_162 |
| PubMedID: 19188831 |
| Title : Different sensitivity of miniature endplate currents in rat external and internal intercostal muscles to the acetylcholinesterase inhibitor C-547 as compared with diaphragm and extensor digitorum longus - Petrov_2009_Physiol.Res_58_149 |
| Author(s) : Petrov KA , Kovyazina IV , Zobov VV , Bukharaeva EA , Nikolsky EE , Vyskocil F |
| Ref : Physiol Res , 58 :149 , 2009 |
| Abstract : Petrov_2009_Physiol.Res_58_149 |
| ESTHER : Petrov_2009_Physiol.Res_58_149 |
| PubMedSearch : Petrov_2009_Physiol.Res_58_149 |
| PubMedID: 19331513 |
| Title : Compounds with the dioxopyrimidine cycle inhibit cholinesterases from different groups of animals - Anikienko_2008_Chem.Biol.Interact_175_286 |
| Author(s) : Anikienko KA , Bychikhin EA , Reznik VS , Akamsin D , Galyametdinova IV |
| Ref : Chemico-Biological Interactions , 175 :286 , 2008 |
| Abstract : Anikienko_2008_Chem.Biol.Interact_175_286 |
| ESTHER : Anikienko_2008_Chem.Biol.Interact_175_286 |
| PubMedSearch : Anikienko_2008_Chem.Biol.Interact_175_286 |
| PubMedID: 18585370 |
| Title : Different sensitivity of miniature endplate currents of the rat extensor digitorum longus, soleus and diaphragm muscles to a novel acetylcholinesterase inhibitor C-547 - Petrov_2006_Physiol.Res_55_585 |
| Author(s) : Petrov KA , Kovyazina LV , Zobov VV , Bukharaeva EA , Nikolsky EE , Vyskocil F |
| Ref : Physiol Res , 55 :585 , 2006 |
| Abstract : Petrov_2006_Physiol.Res_55_585 |
| ESTHER : Petrov_2006_Physiol.Res_55_585 |
| PubMedSearch : Petrov_2006_Physiol.Res_55_585 |
| PubMedID: 16792471 |
| Title : Effect of tetraalkylammonium derivative of 6-methyluracil on amplitude and temporal parameters of miniature endplate potentials in frog neuromuscular junction - Gorshkova_2001_Bull.Exp.Biol.Med_131_446 |
| Author(s) : Gorshkova OV , Zobov VV , Bukharaeva EA , Nikolsky EE , Akamsin VD , Galyametdinova IV , Reznik VS |
| Ref : Bulletin of Experimental Biology & Medicine , 131 :446 , 2001 |
| Abstract : Gorshkova_2001_Bull.Exp.Biol.Med_131_446 |
| ESTHER : Gorshkova_2001_Bull.Exp.Biol.Med_131_446 |
| PubMedSearch : Gorshkova_2001_Bull.Exp.Biol.Med_131_446 |
| PubMedID: 11550049 |