2,5-bis(6-((2-methoxybenzyl)(ethyl)amino)hexylamino)cyclohexa-2,5-diene-1,4-dione

ID: ALA231160

Chembl Id: CHEMBL231160

Max Phase: Preclinical

Molecular Formula: C38H56N4O4

Molecular Weight: 632.89

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Memoquin

Canonical SMILES:  CCN(CCCCCCNC1=CC(=O)C(NCCCCCCN(CC)Cc2ccccc2OC)=CC1=O)Cc1ccccc1OC

Standard InChI:  InChI=1S/C38H56N4O4/c1-5-41(29-31-19-11-13-21-37(31)45-3)25-17-9-7-15-23-39-33-27-36(44)34(28-35(33)43)40-24-16-8-10-18-26-42(6-2)30-32-20-12-14-22-38(32)46-4/h11-14,19-22,27-28,39-40H,5-10,15-18,23-26,29-30H2,1-4H3

Standard InChI Key:  VPXVPJQOPRBXPO-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA231160

    MEMOQUIN

Associated Targets(Human)

APP Tclin Amyloid-beta A4 protein (8510 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SH-SY5Y (11521 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NQO1 Tchem Quinone reductase 1 (1746 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BACE1 Tchem Beta-secretase 1 (15641 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRYZ Tbio Quinone oxidoreductase (9 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Tclin Cholinesterases; ACHE & BCHE (1222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Tclin Butyrylcholinesterase (7174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ache Acetylcholinesterase (12221 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ache Acetylcholinesterase (2577 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 632.89Molecular Weight (Monoisotopic): 632.4302AlogP: 6.27#Rotatable Bonds: 24
Polar Surface Area: 83.14Molecular Species: BASEHBA: 8HBD: 2
#RO5 Violations: 2HBA (Lipinski): 8HBD (Lipinski): 2#RO5 Violations (Lipinski): 2
CX Acidic pKa: CX Basic pKa: 8.51CX LogP: 6.40CX LogD: 4.65
Aromatic Rings: 2Heavy Atoms: 46QED Weighted: 0.10Np Likeness Score: -0.18

References

1. Bolognesi ML, Banzi R, Bartolini M, Cavalli A, Tarozzi A, Andrisano V, Minarini A, Rosini M, Tumiatti V, Bergamini C, Fato R, Lenaz G, Hrelia P, Cattaneo A, Recanatini M, Melchiorre C..  (2007)  Novel class of quinone-bearing polyamines as multi-target-directed ligands to combat Alzheimer's disease.,  50  (20): [PMID:17850125] [10.1021/jm070559a]
2. Cavalli A, Bolognesi ML, Minarini A, Rosini M, Tumiatti V, Recanatini M, Melchiorre C..  (2008)  Multi-target-directed ligands to combat neurodegenerative diseases.,  51  (3): [PMID:18181565] [10.1021/jm7009364]
3. Bolognesi ML, Bartolini M, Rosini M, Andrisano V, Melchiorre C..  (2009)  Structure-activity relationships of memoquin: Influence of the chain chirality in the multi-target mechanism of action.,  19  (15): [PMID:19505825] [10.1016/j.bmcl.2009.05.087]
4. Bolognesi ML, Cavalli A, Bergamini C, Fato R, Lenaz G, Rosini M, Bartolini M, Andrisano V, Melchiorre C..  (2009)  Toward a rational design of multitarget-directed antioxidants: merging memoquin and lipoic acid molecular frameworks.,  52  (23): [PMID:19813747] [10.1021/jm901123n]
5. Melchiorre C, Bolognesi ML, Minarini A, Rosini M, Tumiatti V..  (2010)  Polyamines in drug discovery: from the universal template approach to the multitarget-directed ligand design strategy.,  53  (16): [PMID:20420456] [10.1021/jm100293f]
6. Bolognesi ML, Bartolini M, Tarozzi A, Morroni F, Lizzi F, Milelli A, Minarini A, Rosini M, Hrelia P, Andrisano V, Melchiorre C..  (2011)  Multitargeted drugs discovery: balancing anti-amyloid and anticholinesterase capacity in a single chemical entity.,  21  (9): [PMID:21236667] [10.1016/j.bmcl.2010.12.093]
7. Rosini M, Simoni E, Bartolini M, Tarozzi A, Matera R, Milelli A, Hrelia P, Andrisano V, Bolognesi ML, Melchiorre C..  (2011)  Exploiting the lipoic acid structure in the search for novel multitarget ligands against Alzheimer's disease.,  46  (11): [PMID:21924801] [10.1016/j.ejmech.2011.09.001]
8. Bolognesi ML, Chiriano G, Bartolini M, Mancini F, Bottegoni G, Maestri V, Czvitkovich S, Windisch M, Cavalli A, Minarini A, Rosini M, Tumiatti V, Andrisano V, Melchiorre C..  (2011)  Synthesis of monomeric derivatives to probe memoquin's bivalent interactions.,  54  (24): [PMID:22054058] [10.1021/jm200691d]
9. Prati F, Bartolini M, Simoni E, De Simone A, Pinto A, Andrisano V, Bolognesi ML..  (2013)  Quinones bearing non-steroidal anti-inflammatory fragments as multitarget ligands for Alzheimer's disease.,  23  (23): [PMID:24140444] [10.1016/j.bmcl.2013.09.091]
10. Viayna E, Sola I, Bartolini M, De Simone A, Tapia-Rojas C, Serrano FG, Sabaté R, Juárez-Jiménez J, Pérez B, Luque FJ, Andrisano V, Clos MV, Inestrosa NC, Muñoz-Torrero D..  (2014)  Synthesis and multitarget biological profiling of a novel family of rhein derivatives as disease-modifying anti-Alzheimer agents.,  57  (6): [PMID:24568372] [10.1021/jm401824w]
11. Nepovimova E, Uliassi E, Korabecny J, Peña-Altamira LE, Samez S, Pesaresi A, Garcia GE, Bartolini M, Andrisano V, Bergamini C, Fato R, Lamba D, Roberti M, Kuca K, Monti B, Bolognesi ML..  (2014)  Multitarget drug design strategy: quinone-tacrine hybrids designed to block amyloid-β aggregation and to exert anticholinesterase and antioxidant effects.,  57  (20): [PMID:25259726] [10.1021/jm5010804]
12. Prati F, Uliassi E, Bolognesi ML.  (2014)  Two diseases, one approach: multitarget drug discovery in Alzheimer's and neglected tropical diseases,  (7): [10.1039/C4MD00069B]
13. Zha X, Lamba D, Zhang L, Lou Y, Xu C, Kang D, Chen L, Xu Y, Zhang L, De Simone A, Samez S, Pesaresi A, Stojan J, Lopez MG, Egea J, Andrisano V, Bartolini M..  (2016)  Novel Tacrine-Benzofuran Hybrids as Potent Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease: Design, Synthesis, Biological Evaluation, and X-ray Crystallography.,  59  (1): [PMID:26632651] [10.1021/acs.jmedchem.5b01119]
14. Pan W, Hu K, Bai P, Yu L, Ma Q, Li T, Zhang X, Chen C, Peng K, Liu W, Sang Z..  (2016)  Design, synthesis and evaluation of novel ferulic acid-memoquin hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.,  26  (10): [PMID:27072909] [10.1016/j.bmcl.2016.03.086]
15. Song Q, Li Y, Cao Z, Liu H, Tian C, Yang Z, Qiang X, Tan Z, Deng Y..  (2018)  Discovery of novel 2,5-dihydroxyterephthalamide derivatives as multifunctional agents for the treatment of Alzheimer's disease.,  26  (23-24): [PMID:30470598] [10.1016/j.bmc.2018.11.015]
16. Sang Z, Wang K, Dong J, Tang L..  (2022)  Alzheimer's disease: Updated multi-targets therapeutics are in clinical and in progress.,  238  [PMID:35635955] [10.1016/j.ejmech.2022.114464]

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