112598-96-6

Upstream product

• 3054-95-3 acrylaldehyde diethyl acetal 
• 580-13-2 2-bromonaphthalene 
• 114833-06-6 ethyl (E)-3-(naphthalene-2-yl)acrylate 
• 66-99-9 β-naphthaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 19661-27-9 ethyl 3-(naphthalen-2-yl)acrylate 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 93903-75-4 (2-naphthalenylmethyl)propanedioic acid diethyl ester 
• 2018-90-8 naphthalen-2-ylmethylamine 
• 64-17-5 ethanol 
• 127056-31-9 4-(naphthalen-2-yl)-2-oxobutanoic acid 

Downstream Products

• 136415-67-3 3-(naphthalen-2-yl)propanal 
• 6315-97-5 1-(naphthalen-2-yl)pentan-3-one 

Relevant academic research and scientific papers

Copper(i)-catalysed transfer hydrogenations with ammonia borane

Highly Z-selective alkyne transfer semihydrogenations and conjugate transfer hydrogenations of enoates can be effected by employing a readily available and air-stable copper(i)/N-heterocyclic carbene (NHC) complex, [IPrCuOH]. As an easy to handle and potentially recyclable H2 source, ammonia borane (H3NBH3) is used.

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

4-alkyloxyimino derivatives of uridine-5′-triphosphate: Distal modification of potent agonists as a strategy for molecular probes of P2Y 2, P2Y4, and P2Y6 receptors

Extended N4-(3-arylpropyl)oxy derivatives of uridine-5′-triphosphate were synthesized and potently stimulated phospholipase C stimulation in astrocytoma cells expressing G protein-coupled human (h) P2Y receptors (P2YRs) activated by UTP (P2Y2/4R) or UDP (P2Y6R). The potent P2Y4R-selective N4-(3- phenylpropyl)oxy agonist was phenyl ring-substituted or replaced with terminal heterocyclic or naphthyl rings with retention of P2YR potency. This broad tolerance for steric bulk in a distal region was not observed for dinucleoside tetraphosphate agonists with both nucleobases substituted. The potent N 4-(3-(4-methoxyphenyl)-propyl)oxy analogue 19 (EC50: P2Y2R, 47 nM; P2Y4R, 23 nM) was functionalized for chain extension using click tethering of fluorophores as prosthetic groups. The BODIPY 630/650 conjugate 28 (MRS4162) exhibited EC50 values of 70, 66, and 23 nM at the hP2Y2/4/6Rs, respectively, and specifically labeled cells expressing the P2Y6R. Thus, an extended N4-(3- arylpropyl)oxy group accessed a structurally permissive region on three G q-coupled P2YRs, and potency and selectivity were modulated by distal structural changes. This freedom of substitution was utilized to design of a pan-agonist fluorescent probe of a subset of uracil nucleotide-activated hP2YRs.

Cell-permeable and plasma-stable peptidomimetic inhibitors of the postsynaptic density-95/N-methyl-D-aspartate receptor interaction

The protein-protein interaction between the NMDA receptor and its intracellular scaffolding protein, PSD-95, is a potential target for treating ischemic brain diseases, neuropathic pain, and Alzheimer's disease. We have previously demonstrated that N-alkylated tetrapeptides are potent inhibitors of this interaction, and here, this template is exploited for the development of blood plasma-stable and cell-permeable inhibitors. Initially, we explored both the amino acid sequence of the tetrapeptide and the nature of the N-alkyl groups, which consolidated N-cyclohexylethyl-ETAV (1) as the most potent and selective compound. Next, the amide moieties of N-methylated ETAV were systematically replaced with thioamides, demonstrating that one of three amide bonds could be replaced without compromising the affinity. Subsequent optimization of the N-alkyl groups and evaluation of cell permeability led to identification of N-cyclohexylethyl-ETASV (54) as the most potent, plasma-stable and cell-permeable inhibitor, which is a promising tool in unraveling the therapeutic potential of the PSD-95/NMDA receptor interaction.

Acrolein diethyl acetal: A three-carbon homologating reagent for the synthesis of β-arylpropanoates and cinnamaldehydes by heck reaction catalyzed by a Kaiser oxime resin derived palladacycle

A polymer palladacycle derived from Kaiser oxime resin was used as a source of palladium(0) in the chemoselective Heck reaction of acrolein diethyl acetal with aryl halides under ligand-free conditions. The use of typical Heck conditions afforded 3-arylpropionic esters, and the process can be directed to the synthesis of cinnamaldehydes under Cacchi conditions. These processes take place with rather low loading of the catalyst, which can be recovered by simple filtration and reused for at least five runs without competitive dehalogenation. This is the first time that a supported palladium complex has been reused under Cacchi conditions. ICP-OES analyses of the Pd content of the crude products in both transformations indicated lower leaching for the esters than for the aldehydes in the range up to 0.08 ppm for the esters and 0.8 ppm for the aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Efficient heterogeneously palladium-catalysed heck arylation of acrolein diethyl acetal. Selective synthesis of cinnamaldehydes or 3-arylpropionic esters

A heterogeneous tetrakis(ammine)palladium-NaY zeolite {[Pd(NH 3)4]/NaY] catalyst was applied successfully to the Heck arylation of acrolein diethyl acetal using a large variety of aryl and heteroaryl bromides. Depending on the reaction conditions (Heck versus Cacchi) good to high selectivities toward the 3-arylpropionic esters or to the cinnamaldehydes were achieved, respectively. Under classical Heck conditions, while the catalyst was found to be stable over the two first runs, it showed significant loss of activity from the third cycle. Under Cacchi conditions, the catalyst could not be reused as it led to high dehalogenation rates. All results indicate that the reactions proceed through dissolved palladium species in the bulk solution (leaching). As observed by transmission electronic microscopic (TEM) analyses, while these species can be trapped and stabilised by the zeolite framework under the Heck conditions, they tend to form large palladium(0) aggregates under the Cacchi conditions leading to dehalogenation rather than to the expected Heck coupling.

A novel one-pot conversion of amines to homologated esters in poly(ethylene glycol)

The first deaminative homologation of amines (-CH2NH2) to esters (-CH2CH2COOEt) in one-pot is reported. The reaction proceeds through, formation of an aldehyde from an amine in the presence of Pd/C as catalyst followed by Wittig reaction and catalytic hydrogenation using poly(ethylene glycol) as the solvent in one-pot.

Influence of the catalytic conditions on the selectivity of the Pd-catalyzed Heck arylation of acrolein derivatives

The Heck arylation of acrolein with a variety of condensed aryl and heteroaryl halides is described. Depending on the substrate, up to 87% isolated yield to the expected aldehydes was achieved. When the reaction was run on diethylacetal acrolein, the choice of catalytic system dramatically affected the selectivity of the reaction: the catalyst system based on Herrmann's palladacycle complex gave mainly saturated esters 2, whereas Cacchi's conditions led to the formation of α,β-unsaturated aldehydes 1.

ALPHA-OMEGA-DIARYLALKANE COMPOUNDS SEROTONIN-2 RECEPTOR AGONISTS

Compounds of formula (I): STR1 [wherein: R 1 is aryl; R 2 is hydrogen, alkyl, alkoxy, halogen or cyano; R 3 is a group of formula--B--NR 4 R 5, where R 4 and R 5 are independently hydrogen, alkyl or substituted alkyl or R 4 and R 5, together with the nitr

A NOVEL ENZYME MIMIC FOR THIAZOLIUM-CATALYZED α-KETOACID DECARBOXYLATION

The covalent combination of the thiazolium heterocycle of thiamine with macrotricyclic quaternary ammonium receptor units yields the enzyme mimics 3a,b, which show enhanced substrate selectivity and catalytic activity in decarboxylations of α-ketoacids compared to simpler salts lacking the receptor substructure.