2472-22-2

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-2-tetralone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
6-Methoxy-2-tetralone is used as a key intermediate in the synthesis of various organic compounds, including 1, 2, 3, 4-tetrahydro-2-naphthylamine derivatives. These derivatives have potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
Due to its unique chemical properties, 6-Methoxy-2-tetralone is used in research and development for the exploration of new chemical reactions and the synthesis of novel compounds with potential applications in various fields.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 9, p. 267, 1961 DOI: 10.1248/cpb.9.267The Journal of Organic Chemistry, 26, p. 3237, 1961 DOI: 10.1021/jo01067a049

InChI:InChI=1/C5H8N4.ClH/c1-2-9-4-7-8-5(9)3-6-1;/h4,6H,1-3H2;1H

Upstream product

• 65472-33-5 3,7-dimethoxy-1,2-dihydro-naphthalene 
• 66227-90-5 1-(trimethylsilyl)-3,4-dihydro-6-methoxynaphthalene 
• 5486-55-5 2,6-dimethoxylnaphthalene 
• 83561-51-7 ethyl 2-hydroxy-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-acetate 
• 16821-34-4 cis-6-methoxy-1,2,3,4-tetrahydronaphthalene-1,2-diol 
• 73706-61-3 1-tosyloxy-4-(3-methoxyphenyl)-2-butanone 
• 82167-70-2 6-methoxy-1,2,3,4-tetrahydro 1,2-epoxide 
• 74-85-1 ethene 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 91910-24-6 2-Acetoxy-6-methoxy-3,4-dihydronaphthalin 
• 2311-91-3 monoperoxyphthalic acid 
• 60-29-7 diethyl ether 
• 52178-91-3 7-methoxy-1,2-dihydronaphthalene 
• 93-59-4 Perbenzoic acid 

Downstream Products

• 873965-14-1 6-methoxy-1-(3-methoxy-phenethyl)-3,4-dihydro-1H-naphthalen-2-one 
• 71886-83-4 6-methoxy-1,1-dimethyl-3,4-dihydronaphthalene-2(1H)-one 
• 82763-23-3 N-propyl-6-methoxy-2-aminotetralin 
• 87892-37-3 8-Methoxy-3,4-diphenyl-5,6-dihydrobenzophthalazin 
• 93877-51-1 6-methoxy-2-(p-methoxyphenyl)-3,4-dihydronaphthalene 
• 98130-18-8 3,4-Dihydro-6-methoxy-2-(4-methoxy-m-tolyl)-naphthalin 
• 22117-57-3 3,4-Dihydro-6-methoxy-2-phenylnaphthalene 
• 620171-81-5 6-methoxy-1-(1-trityl-1H-imidazol-4-ylmethylene)-3,4-dihydro-1H-naphthalen-2-one 
• 52802-26-3 2-phenylamino-6-methoxy-(1,2,3,4-tetrahydronaphthalene) 
• 744174-28-5 N-benzyl-6-methoxytetralin-2-amine 
• 237069-32-8 2-(3-formylphenyl)-6-methoxy-3,4-dihydronaphthalene 
• 237069-33-9 2-(4-formylphenyl)-6-methoxy-3,4-dihydronaphthalene 
• 237069-31-7 6-methoxy-2-[4-(1,3-dioxolan-2-yl)phenyl]-3,4-dihydronaphthalene 
• 237069-30-6 6-methoxy-2-[3-(1,3-dioxolan-2-yl)phenyl]-3,4-dihydronaphthalene 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 7-methoxy-1-(3,4,5-trimethoxyphenyl)-4,5-dihydro-2H-benzo[e]indazoles as new colchicine site inhibitors

The colchicine site inhibitors (CSIs) displayed both antimitotic and vascular disrupting activities, therefore are promising potential antitumor agents. In this study, a series 1-phenyl-4,5-dihydro-2H-benzo[e]indazoles were found as new CSIs of which the bioactive configuration was locked. Among them, compounds C1 and C2 displayed the best activity, with tubulin polymerization IC50 of 3.4 and 1.5 μM, and growth IC50 of low nanomolar concentrations against human colon cancer cell lines. In addition, compound C1 showed excellent broad-spectrum antitumor activity in the NCI-60 Human Tumor Cell Lines Screen, encouraging further study of this antitumor compound.

Synthesis of 2-tetralones via a novel 1,2-carbonyl transposition of 1-tetralones

Simple acidic hydrolysis of epoxyamides 4, derived from 1-tetralones, furnishes the corresponding 2-tetralones in good yield.

Carbonyl 1,2-transposition through triflate-mediated a-amination

To date, it remains challenging to selectively migrate a carbonyl oxygen within a given molecular scaffold, especially to an adjacent carbon. In this work, we describe a simple one- or two-pot protocol that transposes a ketone to the vicinal carbon. This approach first converts the ketone to the corresponding alkenyl triflate, which can then undergo the palladium- and norbornene-catalyzed regioselective a-amination and ipso-hydrogenation enabled by a bifunctional hydrogen and nitrogen donor. The resulting "transposed enamine" intermediate can subsequently be hydrolyzed to produce the 1,2-carbonyl-migrated product. This method allows rapid access to unusual bioactive analogs through late-stage functionalization.

Quantum chemistry calculation-aided structural optimization of combretastatin A-4-like tubulin polymerization inhibitors: Improved stability and biological activity

A potent combretastatin A-4 (CA-4) like tubulin polymerization inhibitor 22b was found with strong antitumor activity previously. However, it easily undergoes cis-trans isomerization under natural light, and the resulting decrease in activity limits its further applications. In this study, we used quantum chemistry calculations to explore the molecular basis of its instability. Aided by the calculations, two rounds of structural optimization of 22b were conducted. Accelerated quantitative light stability testing confirmed that the stability of these designed compounds was significantly improved as predicted. Among them, compounds 1 and 3b displayed more potent inhibitory activity on tumor cell growth than 22b. In addition, the potent in vivo antitumor activity of compound 1 was confirmed. Quantum chemistry calculations were used in the optimization of stilbene-like molecules, providing new insight into stilbenoid optimization and important implications for the future development of novel CA-4-like tubulin polymerization inhibitors.

Synthesis and biological evaluation of 1-benzylidene-3,4-dihydronaphthalen- 2-one as a new class of microtubule-targeting agents

A series of 1-benzylidene-3,4-dihydronaphthalen-2-one derivatives were designed and synthesized, and their biological activities in vitro and in vivo were evaluated. The results showed a number of the title compounds exhibiting potent nanomolar activity in several human cancer cell lines. Of these, compound 22b showed the strongest inhibitory activity against human CEM, MDA-MBA-435, and K562 cells (IC50 = 1 nM), displayed in vitro inhibition of tubulin polymerization (IC50 = 3.93 μM), and significantly induced cell cycle arrest in G2/M phase. In addition, compound 22b could inhibit the tumor growth in colon nude mouse xenograft tumor model significantly and seemed safer than CA-4 when achieving a similar tumor suppression. This study provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

TiCl4-promoted intramolecular cyclization of 4-methoxy-5-arylethyl-1,3-dioxolan-2-ones: an expedient method to prepare 2-tetralones

DABCO is a very effective catalyst in the formation of 4-methoxy-5-arylethyl-1,3-dioxolan-2-ones 12 from the corresponding α-carbonatoaldehyde. Intramolecular cyclization of cyclic carbonates 12 promoted by TiCl4 affords 2-tetralones 13 contain

A concise method for the synthesis of 2-tetralone by titanium tetrachloride-promoted cyclization of 4-aryl-2-hydroxybutanal diethyl acetal

4-Aryl-2-hydroxybutanal diethyl acetal, prepared from the reaction of benzyl Grignard reagent and glycidaldehyde diethyl acetal, was treated with titanium tetrachloride to give 2-tetralone in good yield. This highly efficient transformation involves tande

Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1

We report on a series of α-substituted-β-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

Bicyclic antagonists selective for the αvβ3 integrin

This invention provides novel bicyclic compounds of Formula (I): wherein u, v, m, Y, G, A—B, R1, R1a, R2, R4, R5, R5a, and R5b are defined in the specification which compounds exhibit activity as inhibitors of bone resorption and compounds of Formula (II) wherein u, v, m, Y, G, D, A—B, R1, R1a, R2, R3, R4, R5, R5a, and R5b are defined in the specification which compounds exhibit activity as inhibitors of bone resorption.