22009-37-6

Usage

Uses

Used in Pharmaceutical Industry:
7-Methyl-1-tetralone is used as an intermediate in the synthesis of (±)-cis-Calamenene, a sesquiterpene and volatile metabolite derived from Salvia fruticosa plants. 7-Methyl-1-tetralone has potential applications as an antimicrobial, antifungal, and anti-inflammatory agent, making it valuable in the development of new pharmaceuticals for treating various infections and inflammations.
Used in Organic Synthesis:
7-Methyl-1-tetralone is also used as an intermediate in the synthesis of 2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile, which is an intermediate for creating phthalazinone scaffolds. These scaffolds are potent inhibitors of poly(ADP-ribose) polymerase, an enzyme involved in various cellular processes, including DNA repair and genomic stability. The development of inhibitors targeting this enzyme can have significant implications in the treatment of certain diseases and conditions.

InChI:InChI=1/C11H12O/c1-8-5-6-9-3-2-4-11(12)10(9)7-8/h5-7H,2-4H2,1H3

Upstream product

• 104115-64-2 2-bromo-7-methyl-1,2,3,4-tetrahydronapthalin-1-one 
• 121-69-7 N,N-dimethyl-aniline 
• 4521-22-6 4-(4-methylphenyl)butyric acid 
• 160699-02-5 4-(4-methylphenyl)butanoyl chloride 
• 71-43-2 benzene 
• 4619-20-9 3-(4-methylbenzoyl)propionic acid 
• 7664-93-9 sulfuric acid 
• 7719-09-7 thionyl chloride 
• 96-48-0 4-butanolide 
• 108-88-3 toluene 
• 36978-51-5 5-oxo-5-(m-tolyl)pentanoic acid 
• 51114-94-4 (2-carboxyethyl)triphenylphosphonium bromide 
• 62164-86-7 4-(m-tolyl)but-3-enoic acid 
• 59618-44-9 4-(3-methylphenyl)-4-oxobutanoic acid 

Downstream Products

• 102080-30-8 6-methyl-4-phenethyl-1,2-dihydro-naphthalene 
• 6938-37-0 (+/-)-1-Hydroxy-1.7-dimethyl-1.2.3.4-tetrahydro-naphthalin 
• 63039-88-3 9-methyl-12,13-dihydro-7H-dibenzo[a,g]carbazole 
• 29304-62-9 6-methyl-4-phenyl-1,2-dihydro-naphthalene 
• 86499-66-3 8-methyl-1,3,4,5-tetrahydro-benz[b]azepin-2-one 
• 1680-51-9 6-methyl-1,2,3,4-tetrahydronaphthalene 
• 101868-21-7 7-methyl-1-ξ-styryl-naphthalene 
• 6938-36-9 7-Methyl-1,2,3,4-tetrahydro-[1]naphthol 
• 110148-83-9 7-methyl-2-phenethyl-3,4-dihydro-2H-naphthalen-1-one 
• 56137-91-8 7-methyl-naphthyl-1-acetic acid 
• 19723-03-6 7-methyl-1-phenylnaphthalene 
• 2717-47-7 1,2-dihydro-6-methylnaphthalene 
• 52988-07-5 1-(4-methoxyphenyl)-7-methylnaphthalene 
• 58472-26-7 2-hydroxy-7-methylnaphthalene-1,4-dione 

Relevant academic research and scientific papers

Identification of First-in-Class Inhibitors of Kallikrein-Related Peptidase 6 That Promote Oligodendrocyte Differentiation

Multiple sclerosis (MS) is an autoimmune demyelinating disease of the central nervous system (CNS) that causes severe motor, sensory, and cognitive impairments. Kallikrein-related peptidase (KLK)6 is the most abundant serine protease secreted in the CNS, mainly by oligodendrocytes, the myelin-producing cells of the CNS, and KLK6 is assumed to be a robust biomarker of MS, since it is highly increased in the cerebrospinal fluid (CSF) of MS patients. Here, we report the design and biological evaluation of KLK6's low-molecular-weight inhibitors, para-aminobenzyl derivatives. Interestingly, selected hit compounds were selective of the KLK6 proteolytic network encompassing KLK1 and plasmin that also participate in the development of MS physiopathology. Moreover, hits were found noncytotoxic on primary cultures of murine neurons and oligodendrocyte precursor cells (OPCs). Among them, two compounds (32 and 42) were shown to promote the differentiation of OPCs into mature oligodendrocytes in vitro constituting thus emerging leads for the development of regenerative therapies.

Synthesis of Novel Pterocarpen Analogues via [3?+?2] Coupling-Elimination Cascade of α,α-Dicyanoolefins with Quinone Monoimines

By employing triethylamine as a catalyst, [3?+?2] coupling-elimination cascade of α,α-dicyanoolefins with quinone monoimines was realized. The reactions afforded various novel pterocarpen analogues with generally moderate yields (up to 75%). In addition, a plausible reaction mechanism was proposed.

Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

Intramolecular Büchner reaction and oxidative aromatization with SeO2 or O2

Intramolecular Büchner reaction of 1-diazo-5-phenylpentan-2-ones followed by oxidation with SeO2 or O2 in the presence of silica gel regioselectively gave 8-formyl-1-tetralones or one-carbon-lacking 1-tetralones, respectively.

An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β-Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane

An efficient and general trifluoromethylthiolation of silylenol ethers and β-naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α-trifluoromethylthiolated carbonyl compounds and β-naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α-trifluoromethylthiolated (+)-4-cholesten-3-one and naphthoquinone. (Figure presented.).

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7- dihydro-9-(1,2-dihydronaphthalen-4-yl)-5H-benzo[7]annulene derivatives, the question of atropisomerism versus ring inversion

Conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9- (1,2-dihydro- naphthalen-4-yl)-5H-benzo[7]annulene 1 are observed at room temperature in solution. Two conformational processes are possible in 1, i.e. atropisomerism around the sp2-sp2 pivot bond and ring inversion of cycloheptadiene moiety which together provide four minima structures. The 3J calculation by Haasnoot equation on optimized structures is accordance with the 7-substituents in pseudo equatorial (exo) position in both forms. The barrier to conformational process is determined by dynamic 1H-NMR spectroscopy to be δG≠(365K)=74.5±0.5 kJ/mol. Solvent dependent populations of the two forms are studied in DMSO-d6 and CDCl3, the population ratio is not sensitive to solvent polarity. ARKAT USA, Inc.

The marked difference in conformational behavior of the two diastereomers of 7-substituted-1,1-dichloro-7b-((Z)-8-chloro-6,7-dihydro-5H-benzo[7]annulen-9- yl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene, single crystal X-ray, 1H NMR and AM1 studies

The 7-substituted of 1 and 2 were synthesized and conformational analysis carried out. While 7-substituted of 2 show two conformers in solution, 7-substituted of 1 show only one form in solution. AM1 semi-empirical molecular orbital calculations show that the conformation of cycloheptadiene ring in 1 and 2 is a twist boat form. In this conformation, the C-7 substituents can be oriented in pseudo equatorial (exo) and pseudo axial (endo) positions. The 3J calculation with Haasnoot equation on optimized structure of 2 reproduces the observed 3J coupling constants in exo and endo forms. Ring inversion of cycloheptadiene moiety in substituted 2 interconvert the e′-a′ (exo-endo) positions. The 3J calculation on optimized structure of 1 shows that 7-substitution is in pseudo equatorial (exo) direction, as found in the crystal structure of 1a by single crystal X-ray crystallography. The barrier to ring inversion in 2a is determined by dynamic 1H NMR spectroscopy to be ΔG≠(335K) = 68.0 ± 0.5 kJ/mol.

Efficient synthesis of 1-tetralones from 4-arylbutyric acids by combined use of solid acid catalysts and microwave irradiation

Solid acid catalysts such as H-Beta zeolites effectively promote dehydrative intramolecular cyclization of 4-arylbutyric acids under microwave irradiation to give 1-tetralone derivatives in high yields. Copyright

Synthesis and structure-activity relationship studies of 2-(N-substituted)-aminobenzimidazoles as potent negative gating modulators of small conductance Ca2+-activated K+ channels

Small conductance Ca2+-activated K+ channels (SK channels) participate in the control of neuronal excitability, in the shaping of action potential firing patterns, and in the regulation of synaptic transmission. SK channel inhibitors have the potential of becoming new drugs for treatment of various psychiatric and neurological diseases such as depression, cognition impairment, and Parkinson's disease. In the present study we describe the structure-activity relationship (SAR) of a class of 2-(N-substituted)-2- aminobenzimidazoles that constitute a novel class of selective SK channel inhibitors that, in contrast to classical SK inhibitors, do not block the pore of the channel. The pore blocker apamin is not displaced by these compounds in binding studies, and they still inhibit SK channels in which the apamin binding site has been abolished by point mutations. These novel SK inhibitors shift the concentration-response curve for Ca2+ toward higher values and represent the first example of negative gating modulation as a mode-of-action for inhibition of SK channels. The first described compound in this class is NS8593 (14), and the most potent analogue identified in this study is the racemic compound 39 (NS11757), which reversibly inhibits SK3-mediated currents with a Kd value of 9 nM.