3262-03-1

Usage

Uses

1-Chloro-3,4-dihydronaphthalene-2-carbaldehyde

InChI:InChI=1/C11H9ClO/c12-11-9(7-13)6-5-8-3-1-2-4-10(8)11/h1-4,7H,5-6H2

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 56384-70-4 α-tetralone semicarbazone 

Downstream Products

• 138911-91-8 8,10-diamino-5,6-dihydrobenzopyrimido<4,5-b>quinoline 
• 128104-82-5 1-chloro-2-hydroxymethyl-3,4-dihydronaphthalene 
• 111378-93-9 1-<(p-methoxyphenyl)amino>-2-<((p-methoxyphenyl)imino)methyl>-3,4-dihydronaphthalene hydrochloride 
• 6581-76-6 5,6,8,9-tetrahydrodibenzacridine 
• 350691-08-6 1-(2-methylphenyl)-3,4-dihydronaphthalene-2-carbaldehyde 
• 350691-09-7 1-(o-Anisyl)-3,4-dihydronaphtalene-2-carboxaldehyde 
• 113388-94-6 1-phenyl-3,4-dihydro-naphthalene-2-carbaldehyde 
• 183859-96-3 1-phenylethynyl-3,4-dihydronaphthalene-2-carboxaldehyde 
• 861843-76-7 1-(2,5-dimethoxy-phenylamino)-3,4-dihydro-naphthalene-2-carbaldehyde 
• 861843-72-3 (1-chloro-3,4-dihydro-naphthalen-2-ylmethylene)-(2,5-dimethoxy-phenyl)-amine 

Relevant academic research and scientific papers

Discovery and Characterization of Potent Pan-Genotypic HCV NS5A Inhibitors Containing Novel Tricyclic Central Core Leading to Clinical Candidate

The identification of a novel class of potent pan-genotypic NS5A inhibitors with good pharmacokinetic profile suitable for potential use in treating HCV infections is disclosed here. The present series of compounds are with less complex tricyclic central core, identified through a systematic SAR study carried out on biphenyl moiety. The SAR outcome has confirmed the requirement of near planar and linear conformation of the molecule to achieve the best pan-genotypic activity. In addition, SAR with substituted imidazoles on improvement of antiviral activity is disclosed. The newly identified compounds 12, 16, 19-21 have shown desirable pharmacokinetic profiles with a favorable uptake of compounds in liver and maintained a significant concentration for up to 8 h in the liver. In addition, compounds 20 and 21 have shown superior pan-genotypic anti-HCV activity compared to ledipasvir and daclatasvir. Additional characterization and preliminary safety assessment resulted in the identification of compound 20 as a potential clinical candidate.

Synthesis, characterization, photophysical properties of a novel organic photoswitchable dyad in its pristine and hybrid nanocomposite forms

In the present paper the method of synthesis and characterization of a novel organic dyad, 3-(1-Methoxy-3,4-dihydro-naphthalyn-2-yl-)-1-p-chlorophenyl propenone, have been reported. In this paper our main thrust is to fabricate new hybrid nanocomposites by combining the organic dyad with different noble metals, semiconductor nanoparticle and noble metal-semiconductor core/shell nanocomposites. In this organic dyad, donor part is 1-Methoxy-3, 4-dihydro-naphthalen- 2-carboxaldehyde with the acceptor p-chloroacetophenone. We have carried out steady state and time-resolved spectroscopic measurements on the dyad and its hybrid nanocomposite systems. Some quantum chemical calculations have also been done using Gaussian 03 software to support the experimental findings by theoretical point of view. Both from the theoretical predictions and NMR studies it reveals that in the ground state only extended (E-type or trans-type) conformation of the dyad exists whereas on photoexcitation these elongated conformers are converted into folded forms (Z- or cis-type) of the dyad, showing its photoswitchable character. Time resolved fluorescence spectroscopic (fluorescence lifetime by TCSPC method) measurements demonstrate that in chloroform medium all the organic-inorganic hybrid nanocomposites, studied in the present investigation, possess larger amount of extended conformers relative to folded ones, even in the excited singlet state. This indicates the possibility of slower energy destructive charge recombination rates relative to the rate processes associate with charge-separation within the dyad. It was found that in CHCl3 medium, the computed charge separation rate was found to be ～108 s?1 for the dyad alone and other hybrid nanocomposite systems. The rate is found to be faster than the energy wasting charge recombination rate ～102-10 1 s?1, as observed from the transient absorption measurements for the corresponding hybrid systems. It indicates the conformational geometry has a great effect on the charge-separation and recombination rate processes. The suitability for the construction of efficient light energy conversion devices especially with Ag-Dyad nanocomposite of all the systems studied here is hinted from the observed long ion-pair lifetime. Copyright

Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus

Inhibitors for NorA efflux pump of Staphylococcus aureus have attracted the attention of many researchers towards the discovery and development of novel efflux pump inhibitors (EPIs). In an attempt to find specific potent inhibitors of NorA efflux pump of S. aureus, a total of 15 amino acid conjugates of 3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid (4–18) were synthesized using a simple convenient synthetic approach and bioevaluated against NorA efflux pump. Two compounds 7 and 8 (each having MEC of 1.56 μg/mL) were found to restore the activity of ciprofloxacin through reduction of the MIC elucidated by comparing the ethidium bromide efflux in dose dependent manner in addition to ethidium bromide efflux inhibition and accumulation study using NorA overexpressing strain SA-1199B. Most potent compounds among these were able to restore the antibacterial activity of ciprofloxacin completely against SA-1199B. Structure activity relationship (SAR) studies and docking study of potent compounds 7 and 8 could elucidate the structural requirements necessary for interaction with the NorA efflux pumps. On the whole, compounds 7 and 8 have ability to reverse the NorA efflux mediated resistance and could be further optimized for development of potent efflux pump inhibitors.

Photoactuators based on the dynamic molecular crystals of naphthalene acrylic acids driven by stereospecific [2+2] cycloaddition reactions

The photomechanical effects of the dynamic molecular crystals of halogen-substituted naphthalene acrylic acids (1FNaAA, 1ClNaAA, 1BrNaAA, 1INaAA and 6BrNaAA) have been investigated. Upon UV irradiation, the needle-like crystal of 1FNaAA curls away from the light source, while the slice-like crystal of 6BrNaAA bends towards the light source. Moreover, the light-induced bending, flipping and bursting are observed for the elongated needle-like crystals of 1FNaAA, and the slice-like crystals of 1ClNaAA and 1BrNaAA show bending, cracking, coiling, rotating and twisting triggered by 365 nm light. It is found that stereospecific [2+2] cycloaddition reactions take place in the crystals to afford one stereoisomer of β-type cyclobutanes, since 1FNaAA, 1ClNaAA, 1BrNaAA and 6BrNaAA pack in a head-to-head mode, which satisfies the Schmidt's topo-photochemical criteria. The strain can be generated and accumulated during the photodimerization, and the release of the strain leads to the photomechanical effects. This provides new clues for the development of photomechanical molecular crystals based on acrylic acids bearing halogen-substituted aromatic units.

Tricyclic heteroaromatic system amide derivative as well as preparation and application thereof

The invention discloses a tricyclic heteroaromatic system amide derivative. The general formula is as shown in a formula (I), wherein the definitions of R, W1, W2, W3 and W4 are as shown in the specification for details. In addition, the invention also discloses a preparation method and a medicinal composition of the compound. The compound which the invention relates to has high alpha7 receptor binding activity, high selectivity and medium-high-level excitement effect. (The formula is as shown in the description).

Two-Step Synthesis of 3,4-Dihydropyrrolopyrazinones from Ketones and Piperazin-2-ones

An expedient two-step synthesis of 3,4-dihydropyrrolopyrazinones has been achieved via a Vilsmeier-Haack reaction of ketones, followed by an annulation of the corresponding chloroaldehydes with commercially available piperazin-2-ones. A variety of cyclic and acyclic ketones and piperazin-2-ones participated in this two-step chemistry, affording the desired 3,4-dihydropyrrolopyrazinones in up to 78% yield.

4H-Thieno[3,2-c]chromene based inhibitors of Notum Pectinacetylesterase

A group of small molecule thienochromenes inhibitors of Notum Pectinacetylesterase are described. We developed SAR on three series based on carbon, oxygen and sulfur replacement of the 5-position. In each series, highly potent Notum Pectinacetylesterase inhibitors were identified.

Base-Promoted Intermolecular Cyclization of Substituted 3-Aryl(Heteroaryl)-3-chloroacrylaldehydes and Tetrahydroisoquinolines: An Approach to Access Pyrrolo[2,1-a]isoquinolines

We have developed a new base-promoted intermolecular cascade cyclization reaction of substituted 3-aryl(heteroaryl)-3-chloroacrylaldehydes and tetrahydroisoquinolines in one pot. The reaction provides a facile and practical synthesis of pyrrolo[2,1-a]isoquinolines. A number of pyrrolo[2,1-a]isoquinolines were synthesized in moderate to high yields (up to 97%).

Antiviral Compounds with a Heterotricycle Moiety

Disclosed are compounds of formula (I) for use as antiviral agents, particularly as anti-hepatitis virus C agents, wherein A, B, U, R1-R7, m, n, and q are as described herein. Also disclosed are pharmaceutical compositions and methods of treating or preventing viral infection in a host by the use of these compounds, either alone or in combination with other pharmaceutically active agents. Further disclosed are methods of preparing such compounds.

Modular Synthesis of Highly Substituted Pyridines via Enolate α-Alkenylation

A novel methodology for the synthesis of highly substituted pyridines based on the palladium-catalyzed enolate α-alkenylation of ketones is presented; the formation of aromatic compounds is a new direction for this catalytic C-C bond forming reaction. In the key step, a protected β-haloalkenylaldehyde participates in α-alkenylation with a ketone to afford a 1,5-dicarbonyl surrogate, which then undergoes cyclization/double elimination to the corresponding pyridine product, all in one pot. The β-haloalkenylaldehyde starting materials can be obtained from the corresponding methylene ketone via Vilsmeier haloformylation. Using this concise route, a variety of highly substituted pyridines were synthesized in three steps from commercially available compounds. (Chemical Equation Presented).