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

Target

Families : C-547 ligand of proteins in family
ACHE

Structure :
5FKJ

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 :
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 :
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 :
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 :
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 :
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 :
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 :
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 :
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 :
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 :
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 :
PubMedSearch : Gorshkova_2001_Bull.Exp.Biol.Med_131_446
PubMedID: 11550049