259739-01-0

Basic information

• Product Name: DMEAN
• Synonyms: (2-(1,1-DICYANOPROPEN-2-YL)-6-METHYL-(2-HYDROXOETHYL)-AMINO)-NAPHTHALENE;2-(1-(6-[((2-HYDROXY)ETHYL)(METHYL)AMINO]-2-NAPHTHYL)ETHYLIDENE)MALONITRILE;2-(1-(6-[((2-HYDROXY)ETHYL)(METHYL)AMINO]-2-NAPHTHYL)ETHYLIDEN)MALONITRILE;DMEAN;PROPANEDINITRILE, [1-[6-[METHYL[2-[HYDROXY]ETHYL]AMINO]-2-NAPHTHALENYL]ETHYLIDENE]-
• CAS NO: 259739-01-0
• Molecular Formula: C₁₈H₁₇N₃O
• Molecular Weight: 291.35
• Mol File: 259739-01-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DMEAN(CAS DataBase Reference)
• NIST Chemistry Reference: DMEAN(259739-01-0)
• EPA Substance Registry System: DMEAN(259739-01-0)

Safety Data

• Hazardous Substances Data: 259739-01-0(Hazardous Substances Data)

Usage

Chemical Properties

Reddish solid

Upstream product

• 109-77-3 malononitrile 
• 259739-00-9 1-(6-((2-hydroxyethyl)(methyl)amino)naphthalen-2-yl)ethan-1-one 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 10441-41-5 1-(6-hydroxy-2-naphthyl)ethan-1-one 

Downstream Products

• 259739-02-1 2-{[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl](methyl)amino}ethyl-4-methylbenzenesulfonate 
• 1262387-15-4 2-(1,1-dicyanopropen-2-yl)-6-(2-(4-(2-cyclohexyl)ethyl)benzenesulfonyloxyethyl)methylamino-naphthalene 

Relevant articles and documents

Method of fabricating [F-18]FEONM precursor

A [F-18]FEONM precursor is synthesized. 2-bromoethanol is added to further connect an atom of oxygen at an N terminal of the precursor. Four atoms of carbon can be further connected. Thus, better fat-solubility is obtained along with the increase in carbon. Positioning in brain imaging becomes better.

Method of Fabricating Precursor of [F-18]FEONM

A [F-18]FEONM precursor is synthesized. 2-bromoethanol is added to further connect an atom of oxygen at the N terminal. Thus, four atoms of carbon can be further connected to obtain relatively better solubility for better positioning in brain imaging.

Synthesis and optical properties of 4-(2-{[6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl] (methyl)amino} ethoxy)-4-oxobutanoic acid fluorescent probe for β-amyloid

Abstract A novel 4-(2-{[6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl](methyl)amino} ethoxy)-4-oxobutanoic acid (5) fluorescent probe for β-amyloids was synthesized by catalytic acylation using 4-dimethylaminopyridine between succinic anhydride and (1-{6-[(2-hydroxyethyl)(methyl) amino]-2-naphthyl}ethylidene)malononitrile (4). The structures of all compounds were identified by proton nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and ultraviolet-visible (UV-Vis) spectroscopy. The UV-Vis and fluorescence spectra of 1-{6-[(2-hydroxyethyl)(methyl) amino]-2-naphthyl}ethan-1-one (3), 4, and 5 in solvents with different polarities were investigated, and the effects of solvent polarity on the optical properties of the three compounds were studied. The objective product 5 showed high binding affinities toward Aβ(1-40) aggregates in vitro (K d = 29.4 nmol/L) by fluorophotometry. This study provides a powerful fluorescent probe for the molecular diagnosis of Alzheimer's disease.

Compound of radiocontrast agent for tau protein

A radiocontrast agent for tau protein is provided. The agent is selectively and strongly bound to tau protein and its tangle found in brain diseases like Alzheimer's disease (AD). The agent is especially suitable to be used in PET imaging for brain diseases. Or, the agent can be used to inhibit tau protein overexpressive and, thus, stop the proceeding of brain disease.

99mTc- and Re-labeled 6-dialkylamino-2-naphthylethylidene derivatives as imaging probes for β-amyloid plaques

Based on the conjugate strategy, two neutral 99mTc labeled 2-(1-(6-(dialkylamino)naphthalen-2-yl)ethylidene)malononitrile (DDNP) and 1-(6-(dialkylamino)naphthalen-2-yl)ethanone (ENE) derivatives, and their corresponding rhenium complexes were synthesized. In vitro fluorescent staining indicated that the corresponding rhenium derivatives selectively stained the β-amyloid (Aβ) plaques in the brain sections of AD model mice with low background. Compared with FDDNP and FENE, the affinities of the corresponding rhenium derivatives to Aβ aggregates decreased about 10-14-fold. In vivo biodistribution experiments in normal mice showed that 99mTc-MAMA-ENE displayed medium initial brain uptake (0.65 %ID/g at 2 min) with a reasonable washout from the brain (0.19 %ID/g at 2 h) while 99mTc-MAMA-DDNP showed a low brain uptake (0.28 %ID/g at 2 min). Further optimize these 99mTc-labeled tracers in order to improve their binding affinities to Aβ plaques and diffusion through the blood brain barrier may generate useful imaging agents for SPECT.

Methods for binding agents to b-amyloid plaques

A method for labeling structures, such as β-amyloid plaques and neurofibrillary tangles, in vivo or in vitro, is provided and comprises contacting brain tissue with one or more compounds, preferably radiolabeled for detection by positron emission tomography (PET).