14607-11-5

Upstream product

• 642-31-9 9-anthracene aldehyde 
• 100-46-9 benzylamine 

Downstream Products

• 57447-07-1 9-[(N-benzylamino)methyl]anthracene 
• 797763-33-8 (+/-)-diethyl 1-(benzylamino)-1-(9-anthryl)methylphosphonate 
• 57447-08-2 N-Benzyl-N-propargyl-9-anthracenemethanamine 
• 56948-89-1 2-Benzyl-1,2,3,5-tetrahydro-5,9b-o-benzenobenzisoindole 
• 209669-45-4 Bis-anthracen-9-ylmethyl-benzyl-amine 

Relevant academic research and scientific papers

Specific sensing between inositol epimers by a bis(boronate)

Bis(boronates) that utilize internal photoinduced electron transfer (PET) quenching mechanisms can specifically signal the binding of chiro-inositol without responding to its epimer, myo-inositol.

Evaluating hydrogen bonding control in the diastereoselective Diels-Alder reactions of 9-(2-aminoethyl)-anthracene derivatives

Several 9-(2-aminoethyl)anthracene derivatives were prepared with different nitrogen substitutents including alkyl, acetamide, trifluoroacaeamide and t-butyl carbamate. The selectivity in Diels-Alder cyclodaddition reaction with N-methyl maleimide was evaluated through single crystal X-ray analysis of the products. Models for the change in selectivity with hydrogen bond acceptor are proposed, supported by DFT level calculations.

Hydrogen-bonded complexes of aromatic crown ethers with (9-anthracenyl)methylammonium derivatives. Supramolecular photochemistry and photophysics. PH-controllable supramolecular switching

The (9-anthracenyl)methylammonium and (9-anthracenyl)benzylammonium tetrakis(hexafluorophosphate) salts give hydrogen-bonded complexes in CH2Cl2 with aromatic crown ethers containing dibenzo (DB) or dinaphtho (DN) units. The association constants vary from 3 x 103 to 1 x 106 M-1 in CH2Cl2, depending on the specific ammonium cation and crown ether involved. In a number of cases, pseudorotaxane-like geometries for the complexes are demonstrated by (a) 1H NMR spectroscopy in solution, (b) X-ray crystallography in the solid state, and (c) mass spectrometry in the gas phase. The results obtained by absorption, emission, and excitation spectroscopy and excited lifetimes show that, as a consequence of the hydrogen bond driven recognition process, the anthracene chromophoric unit interacts with the aromatic units of the crown ethers. In the complexes involving the DB18C6, DB24C8, and DB30C10 macrocycles, the interaction leads to the complete quenching of the fluorescence of the dialkoxybenzene moieties and parallels sensitization of the anthracene fluorescence. In the complexes of 1/5-DN38C10, both the crown and the anthracene fluorescence are completely quenched, most likely by an energy-transfer cascade involving the triplet state of the dialkoxynaphthalene moiety. In the complexes of 2/3-DN30C10, the interaction between the anthracene moiety and the naphthalene rings of the crown ether is relatively strong, as indicated by the perturbation of the absorption bands, the disappearance of the fluorescence bands of the naphthalene- and anthracene-type chromophoric units, and the appearance of a new, broad fluorescence band. The complexes can also be formed by addition of CF3COOH or CF3SO3H to CH2Cl2 solutions containing crown ether and amine. The association process between DB24C8 and (9-anthracenyl)benzylammonium salt can be reversed quantitatively upon addition of a suitable base and the complex can be formed again after treatment with acid.

Polycyclic maleimide-based derivatives as first dual modulators of neuronal calcium channels and GSK-3β for Alzheimer's disease treatment

Current healthcare has significantly increased the average life expectancy, leading to a consequently greater incidence of age-related diseases, such as Alzheimer's disease. Following a multitarget approach, in this paper a series of polycyclic maleimide-based derivatives were designed and synthesized aimed at simultaneously modulate neuronal calcium channels and glycogen synthase kinase 3-beta (GSK-3β), validated targets to combat Alzheimer’ disease. Different structural modifications were performed on the polycyclic scaffold in order to investigate the structure-activity relationships and compound 10 emerged as a promising non-toxic lead compound, endowed with calcium modulating brain-addressed properties and significant GSK-3β inhibitory activity. Moreover, the easily affordable polycyclic core appears as a new appealing privileged structure in medicinal chemistry.

Molecular interactions, proton exchange, and photoinduced processes prompted by an inclusion process and a [2]pseudorotaxane formation

Appropriate design of the host and guest components allows formation of a novel [2]pseudorotaxane complex with an interrupted photoinduced electron transfer (PET)-coupled fluorescence resonance energy transfer (FRET) response. This is the first example of an inclusion complex with NO6-based azacrown ether as the host unit (H). Different guest molecules (G1, G2, G3, and G4) with varying stopper size are used for the studies. Unlike G1, G2, and G3, G4 with a relatively bulkier stopper fails to form a [2]pseudorotaxane complex. Isothermal titration microcalorimetry measurements reveal a systematic increase in the association constant for H·G1, H·G2, and H·G3 with a change in the stopper size. Thermodynamic data suggest that the formation of H·G1/H·G2/H·G3 is exclusively driven by a large positive entropic gain (TΔS = 19.69/26.80/21.81 kJ·mol-1), while the enthalpy change is slightly negative for H·G1/H·G3 (-2.61/-1.97 kJ·mol-1) and slightly positive for H·G2 (ΔH = 5.98 kJ·mol-1). For these three inclusion complexes, an interrupted PET-coupled FRET response is observed with varying efficiency, which is attributed to the subtle differences in acidity of the NH2+ unit of the guest molecules and thus the proton exchange ability between the host and respective guest. This is substantiated by the results of the computational studies.

Unexpected non-stability of aminophosphonates: Limitation of their synthesis using diphenylmethylamine procedure

New diethyl 1-diphenylmethylaminoalkylphosphonates from aldehydes, ketones, diphenylmethylamine and diethyl phosphite were obtained. Their stability in acidic media as determined by 31P NMR spectroscopy strongly depends on the basicity of the nitrogen atom. The bulky N-substituent can drastically decrease the stability of the ester during acidic hydrolysis leading to decomposition products in the retro Kabachnik-Fields like reaction.

Syntheses and photoreactivity of new bisanthracenes incorporating 1 or 2 nitrogen atoms in the linkage

Three new bisanthracenes (1-3) incorporating 1 or 2 nitrogen atoms in the linkage exibit low photoreactivity towards intramolecular dimerization which is assigned to an intramolecular electron-transfer from the amino group towards the excited anthracene and to the poor flexibility of the chain tethering the chromophores.

Intramolecular Diels-Alder Additions. 1. Additions to Anthracene and Acridine

Intramolecular Diels-Alder reaction of suitably 9-substituted anthracenes at temperatures ranging from 25 to 220 deg C yields a wide variety of 9,12-bridged ethano- and ethenoanthracenes.Adducts having tree-, four-, and five-membered bridges, many incorporating heteroatoms such as oxygen, nitrogen, and sulfur, have been prepared.The ease of cyclization decreases with increasing bridge length.Neither the diene nor the dienophile need to carry activating groups; vinyl and ethynyl dienophiles add with equal ease.Cyclization of N-methyl-N-propargyl-9-acridinecarboxamide gives 31, the first thermal adduct of an acridine.