AP2238 - CAS 553681-56-4
Catalog number: 553681-56-4
Category: Inhibitor
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Molecular Formula:
C26H25NO4
Molecular Weight:
415.48
COA:
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Targets:
AChE
Description:
AP2238 is a inhibitor of both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation.
Purity:
98%
Appearance:
Solid powder
Synonyms:
AP-2238; AP 2238; AP2238; CHEMBL75121; UNII-545225E0BC; BDBM10949; DNC007569; 2H-1-Benzopyran-2-one, 6,7-dimethoxy-3-(4-((methyl(phenylmethyl)amino)methyl)phenyl)-;3-[4-(N-Benzyl-N-methylaminomethyl)phenyl]-6,7-dimethoxy-2H-1-benzopyran-2-one
Solubility:
Soluble in DMSO, not in water
Storage:
-20°C Freezer
MSDS:
Inquire
Quality Standard:
In-house standard
Quantity:
Milligrams-Grams
Boiling Point:
568.9±50.0 °C | Condition: Press: 760 Torr
Density:
1.205±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
KXMCSAUVAHKCOR-UHFFFAOYSA-N
InChI:
InChI=1S/C26H25NO4/c1-27(16-18-7-5-4-6-8-18)17-19-9-11-20(12-10-19)22-13-21-14-24(29-2)25(30-3)15-23(21)31-26(22)28/h4-15H,16-17H2,1-3H3
Canonical SMILES:
CN(CC1=CC=CC=C1)CC2=CC=C(C=C2)C3=CC4=CC(=C(C=C4OC3=O)OC)OC
1.From the dual function lead AP2238 to AP2469, a multi-target-directed ligand for the treatment of Alzheimer's disease.
Tarozzi A;Bartolini M;Piazzi L;Valgimigli L;Amorati R;Bolondi C;Djemil A;Mancini F;Andrisano V;Rampa A Pharmacol Res Perspect. 2014 Apr;2(2):e00023. doi: 10.1002/prp2.23. Epub 2014 Mar 24.
The development of drugs with different pharmacological properties appears to be an innovative therapeutic approach for Alzheimer's disease. In this article, we describe a simple structural modification of AP2238, a first dual function lead, in particular the introduction of the catechol moiety performed in order to search for multi-target ligands. The new compound AP2469 retains anti-acetylcholinesterase (AChE) and beta-site amyloid precursor protein cleaving enzyme (BACE)1 activities compared to the reference, and is also able to inhibit Aβ 42 self-aggregation, Aβ 42 oligomer-binding to cell membrane and subsequently reactive oxygen species formation in both neuronal and microglial cells. The ability of AP2469 to interfere with Aβ 42 oligomer-binding to neuron and microglial cell membrane gives this molecule both neuroprotective and anti-inflammatory properties. These findings, together with its strong chain-breaking antioxidant performance, make AP2469 a potential drug able to modify the course of the disease.
2.Multitarget Strategy to Address Alzheimer's Disease: Design, Synthesis, Biological Evaluation, and Computational Studies of Coumarin-Based Derivatives.
Montanari S;Bartolini M;Neviani P;Belluti F;Gobbi S;Pruccoli L;Tarozzi A;Falchi F;Andrisano V;Miszta P;Cavalli A;Filipek S;Bisi A;Rampa A ChemMedChem. 2016 Jun 20;11(12):1296-308. doi: 10.1002/cmdc.201500392. Epub 2015 Oct 28.
Alzheimer's disease (AD) is a major public health challenge that faces an aging global population. Current drug treatment has demonstrated only symptomatic efficacy, leaving an unmet medical need for a new generation of disease-modifying therapies. Following the multitarget-directed ligand approach, a small library of coumarin-based derivatives was designed and synthesized as a follow-up to our studies on AP2238, aimed at expanding its biological profile. The coumarin substitution pattern at the 6- or 7-position was modified by introducing alkyl chains of variable lengths and with different terminal amino functional groups. 3-(4-{[Benzyl(ethyl)amino]methyl}phenyl)-6-({5-[(7-methoxy-6H-indeno[2,1-b]quinolin-11-yl)amino]pentyl}oxy)-2H-chromen-2-one, bearing the bulkiest amine, emerged as a non-neurotoxic dual acetylcholinesterase (AChE)/butyrylcholinesterase (BuChE) inhibitor, potentially suitable for the treatment of the middle stage of AD. Furthermore, the introduction of a diethylamino spacer, as in 3-(4-{[benzyl(ethyl)amino]methyl}phenyl)-6-{[5-(diethylamino)pentyl]oxy}-2H-chromen-2-one and 3-(4-{[benzyl(ethyl)amino]methyl}phenyl)-7-[4-(diethylamino)butoxy]-2H-chromen-2-one, led to nanomolar human AChE inhibitors endowed with significant inhibitory activity toward Aβ42 self-aggregation, whereas the reference compound was completely ineffective.
3.Multi-target-directed coumarin derivatives: hAChE and BACE1 inhibitors as potential anti-Alzheimer compounds.
Piazzi L;Cavalli A;Colizzi F;Belluti F;Bartolini M;Mancini F;Recanatini M;Andrisano V;Rampa A Bioorg Med Chem Lett. 2008 Jan 1;18(1):423-6. Epub 2007 Oct 4.
The complex etiology of Alzheimer's disease (AD) prompts scientists to develop multifunctional compounds to combat causes and symptoms of such neurodegeneration. To this aim we designed, synthesized, and tested a series of compounds by introducing halophenylalkylamidic functions on the scaffold of AP2238, which is a dual binding site acetylcholinesterase inhibitor. The inhibitory activity was successfully extended to the beta-site amyloid precursor protein cleavage enzyme, leading to the discovery of a potent inhibitor of this enzyme (3) and affording multifunctional compounds (2, 6, 8) for the treatment of AD.
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