5426-19-7

Usage

Chemical compound

4-[2-(naphthalen-1-yl)ethyl]pyridine

Upstream product

• 108-89-4 picoline 
• 4780-79-4 1-naphthalene methanol 
• 16375-56-7 4-[2-(1-naphtalenyl)ethenyl]-pyridine 
• 86-52-2 1-Chloromethylnaphthalene 
• 66-77-3 1-naphthaldehyde 
• 16375-78-3 trans-1-(1-Naphthyl)-2-(4'-pyridyl)ethylene 

Relevant academic research and scientific papers

Molecular Size and Flexibility as Determinants of Selectivity in the Oxidation of N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine Analogs by Monoamine Oxidase A and B

The introduction of a methylene bridge between the phenyl and tetrahydropyridyl moieties of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) results in increased selectivity for monoamine oxidase B (MAO B) over monoamine oxidase A (MAO A). However, lengthening of this bridge results in a total loss of selectivity. In the present study, a number of isomeric 4-naphthyl-, 4-(naphthylalkyl)-, 4-thienyl-, and 4-(thienylalkyl)tetrahydropyridines, conformationally restrained and flexible analogs of MPTP, were synthesized and evaluated as potential selective substrates of MAO A and B. In terms of the parameter (turnover number)/Km, the bulky naphthyl analogs were invariably better substrates of MAO A than kynuramine, the reference substrate for this enzyme. In addition, all naphthyl analogs, regardless of conformational mobility, were more effective substrates of MAO A than MAO B. Similarly, all thienyl analogs were found to be more effective substrates of MAO B. In contrast to the naphthalenes, the conformationally restrained thiophenes 9a and 10a were found to be poor substrates of MAO B, relative to benzylamine, the reference substrate. These results suggest that the selectivity of these compounds for either MAO A or B is determined by the complex interplay of molecular size and flexibility. In this interplay, either one of these two factors may predominate.

In Situ Assembly of Choline Acetyltransferase Ligands by a Hydrothiolation Reaction Reveals Key Determinants for Inhibitor Design

The potential drug target choline acetyltransferase (ChAT) catalyses the production of the neurotransmitter acetylcholine in cholinergic neurons, T-cells, and B-cells. Herein, we show that arylvinylpyridiniums (AVPs), the most widely studied class of ChAT inhibitors, act as substrate in an unusual coenzyme A-dependent hydrothiolation reaction. This in situ synthesis yields an adduct that is the actual enzyme inhibitor. The adduct is deeply buried in the active site tunnel of ChAT and interactions with a hydrophobic pocket near the choline binding site have major implications for the molecular recognition of inhibitors. Our findings clarify the inhibition mechanism of AVPs, establish a drug modality that exploits a target-catalysed reaction between exogenous and endogenous precursors, and provide new directions for the development of ChAT inhibitors with improved potency and bioactivity.

Iridium-Catalyzed C-Alkylation of Methyl Group on N-Heteroaromatic Compounds using Alcohols

In this study, we developed a catalytic system for the C-alkylation of a methyl group on N-heteroaromatic compounds, including pyridine, pyrimidine, pyrazine, quinoline, quinoxaline, and isoquinoline, using alcohols based on a hydrogen-borrowing process with [Cp*IrCl2]2 (Cp*: η5-pentamethylcyclopentadienyl) combined with potassium t-butoxide and 18-crown-6-ether as the catalyst precursor.

Interaction between a pyridyl and a naphthyl/pyrenyl moiety in covalently linked systems

Photophysical properties of two bichromophoric systems comprising a pyridyl moiety and a naphthyl/pyrenyl moiety covalently linked through a dimethylene bridge have been investigated. The spectral behavior of the systems suggests the formation of an intramolecular complex between the two terminal moieties of the molecules in the ground state. Interestingly, no intermolecular complexation could be observed with a 1:1 mixture of the constituting components. This contrasting behavior has been interpreted taking into consideration the difference in the entropy change associated with the complexation process. Based on the effect of solvent polarity on the absorption and emission behavior of the complex and taking into consideration the molecular geometry, it is concluded that the interaction between the aromatic hydrocarbon and pyridyl moieties is primarily driven through an overlap of the π-clouds.

Approaches to Protection against Nerve Agent Poisoning. (Naphthylvinyl)pyridine Derivatives as Potential Antidotes

Analogues of the potent inhibitor of choline acetyltransferase (CAT) (E)-4-(1-naphthylvinyl)pyridine methiodide were synthesized and evaluated for their ability to inhibit CAT and protect against nerve agent intoxication.Several compounds, notably (E)-1-(2-hydroxyethyl)-(1-naphthylvinyl)pyridinium bromide (3), (E)-1-methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine hydrochloride (22), and (E)-1-methyl-4-(1-naphthylvinyl)piperidine hydrochloride (23), were found to afford significant protection against sarin in the mouse and against soman in the giunea pig.However, protection was apparently not related to CAT inhibition.Compound 23, our most effective compound in protecting against nerve agent, was without CAT inhibitory activity.Compound 22, which proved to be a potent CAT inhibitor, most likely owed this activity to being dehydrogenated back to the pyridinium quaternary salt by oxidative enzymes.Several of the (naphthylvinyl)pyridine quaternary salts, but not their tertiary amine analogues, were found to be effective in slowing the rate of aging of soman-inhibited acetylcholinesterase.Ability to slow the rate of aging was enhanced by introduction of methoxy substituents on the aryl moiety whereas the aging rate was actually accelerated by chloro substituents.To date, our most effective compound in slowing the rate of aging, (E)-4-pyridine methochloride (6), did not provide significant protection against soman in the mouse.