- Regioselective Electrochemical Cyclobutanol Ring Expansion to 1-Tetralones
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A mild electrochemical method for the regioselective preparation of 1-tetralones under environmentally friendly conditions from readily available cyclobutanols was developed. A series of aromatic- and heteroaromatic-fused 1-tetralones was accessed through ring expansion of the functionalized cyclobutanols via electrochemical generation of alkoxy radicals and intramolecular cyclization.
- Petti, Alessia,Natho, Philipp,Lam, Kevin,Parsons, Philip J.
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p. 854 - 858
(2021/01/12)
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- Bridged Stilbenes: AIEgens Designed via a Simple Strategy to Control the Non-radiative Decay Pathway
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To broaden the application of aggregation-induced emission (AIE) luminogens (AIEgens), the design of novel small-molecular dyes that exhibit high fluorescence quantum yield (Φfl) in the solid state is required. Considering that the mechanism of
- Igawa, Kazunobu,Iwai, Riki,Konishi, Gen-ichi,Morokuma, Keiji,Sairi, Amir Sharidan,Sasaki, Shunsuke,Suenobu, Tomoyoshi,Suzuki, Satoshi
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supporting information
p. 10566 - 10573
(2020/04/15)
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- Intramolecular Büchner reaction and oxidative aromatization with SeO2 or O2
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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.
- Morita, Shunya,Yoshimura, Tomoyuki,Matsuo, Jun-ichi
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p. 729 - 732
(2019/07/31)
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- Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light
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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.
- Sherwood, Trevor C.,Xiao, Hai-Yun,Bhaskar, Roshan G.,Simmons, Eric M.,Zaretsky, Serge,Rauch, Martin P.,Knowles, Robert R.,Dhar, T. G. Murali
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p. 8360 - 8379
(2019/09/03)
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- 6 - Substituted aryl amino methyl tetralin derivatives or salts thereof, and its preparation and use
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The invention provides a 6-substituted aryl amino methyl tetrahydronaphthalene derivative or salt thereof and a preparation method and application of the 6-substituted aryl amino methyl tetrahydronaphthalene derivative, belongs to the pharmaceutical field
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Paragraph 0037; 0038; 0039; 0052; 0053; 0054; 0055; 0056
(2018/04/02)
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- Method for synthesizing tetralone compound
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The invention belongs to the technical field of organic compound synthesis, provides a method for synthesizing a tetralone compound, and aims at solving the problems that in an exiting tetralone compound synthesizing method, an expensive transition metal catalyst, such as a palladium catalyst, is needed, and a large quantity of oxidizing agent is needed during a reaction. Aryl is used for replacing cyclobutanol to serve as an initiator, under the action of a catalyst, an oxidizing agent and an additive, reacting is carried out for 1-8 h in a solvent at the temperature of 25 DEG C to 100 DEG C, and the tetralone compound is obtained. The method has the advantages that the reaction conditions are relatively moderate, cheap metal copper is adopted as the catalyst, ligand participation is not needed, and operation is easy, convenient and feasible.
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Paragraph 0026; 0027
(2016/10/07)
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- Discovery of Potent and Selective Agonists of δ Opioid Receptor by Revisiting the "message-Address" Concept
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The classic "message-address" concept was proposed to address the binding of endogenous peptides to the opioid receptors and was later successfully applied in the discovery of the first nonpeptide δ opioid receptor (DOR) antagonist naltrindole. By revisiting this concept, and based on the structure of tramadol, we designed a series of novel compounds that act as highly potent and selective agonists of DOR among which (-)-6j showed the highest affinity (Ki = 2.7 nM), best agonistic activity (EC50 = 2.6 nM), and DOR selectivity (more than 1000-fold over the other two subtype opioid receptors). Molecular docking studies suggest that the "message" part of (-)-6j interacts with residue Asp1283.32 and a neighboring water molecule, and the "address" part of (-)-6j packs with hydrophobic residues Leu3007.35, Val2816.55, and Trp2846.58, rendering DOR selectivity. The discovery of novel compound (-)-6j, and the obtained insights into DOR-agonist binding will help us design more potent and selective DOR agonists.
- Shen, Qing,Qian, Yuanyuan,Huang, Xiaoqin,Xu, Xuejun,Li, Wei,Liu, Jinggen,Fu, Wei
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p. 391 - 396
(2016/05/19)
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- A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion
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A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.
- Yu, Jiajia,Zhao, Huijun,Liang, Shuguang,Bao, Xiaoguang,Zhu, Chen
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supporting information
p. 7924 - 7927
(2015/07/27)
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- Tetrahydronaphthalene-derived amino alcohols and amino ketones as potent and selective inhibitors of the delayed rectifier potassium current I Ks
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Class III anti-arrhythmic drugs (e.g., dofetilide) prolong cardiac action potential duration (APD) by blocking the fast component of the delayed rectifier potassium current (IKr). The block of IKr can result in life threatening ventr
- Ahmad, Saleem,Doweyko, Lidia,Ashfaq, Aaila,Ferrara, Francis N.,Bisaha, Sharon N.,Schmidt, Joan B.,DiMarco, John,Conder, Mary Lee,Jenkins-West, Tonya,Normandin, Diane E.,Russell, Anita D.,Smith, Mark A.,Levesque, Paul C.,Lodge, Nicholas J.,Lloyd, John,Stein, Philip D.,Atwal, Karnail S.
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- Bicyclic N-hydroxyurea inhibitors of 5-lipoxygenase: Pharmacodynamic, pharmacokinetic, and in vitro metabolic studies characterizing N-hydroxy-N-(2,3-dihydro-6-(phenylmethoxy)-3-benzofuranyl)urea
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A series of N-hydroxyurea derivatives have been prepared and examined as inhibitors of 5-lipoxygenase. Oral activity was established by examining the inhibition of LTB4 biosynthesis in an ex vivo assay in the mouse. The pharmacodynamic performance in the mouse of selected compounds was assessed using an ex vivo LTB4 assay and an adoptive peritoneal anaphylaxis assay at extended pretreat times. Compounds with an extended duration of action were reexamined as the individual enantiomers in the ex vivo assay, and the (S) enantiomer of N-hydroxy-N-[2,3-dihydro-6-(phenylmethoxy)-3-benzofuranyl]urea, (+)-1a (SB 202235), was selected as the compound with the best overall profile. Higher plasma concentrations and longer plasma half-lives were found for (+)-1a relative to its enantiomer in the mouse, monkey, and dog. In vitro metabolic studies in mouse liver microsomes established enantiospecific glucuronidation as a likely mechanism for the observed differences between the enantiomers of 1a. Enantioselective glucuronidation favoring (-)-1a was also found in human liver microsomes.
- Adams, Jerry L.,Garigipati, Ravi S.,Sorenson, Margaret,Schmidt, Stanley J.,Brian, William R.,Newton, John F.,Tyrrell, Kathy A.,Garver, Eric,Yodis, Lee A.,Chabot-Fletcher, Marie,Tzimas, Maritsa,Webb, Edward F.,Breton, John J.,Griswold, Don E.
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p. 5035 - 5046
(2007/10/03)
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- A short, efficient synthesis of 6-cyano-1-tetralones
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A new, short and high-yield synthesis of 6-cyano-1-tetralones is described. Triflate intermediates 8 and 9 are versatile intermediates for the synthesis of other 6-substituted tetralones.
- Almansa,Carceller,Bartroli,Forn
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p. 2965 - 2971
(2007/10/02)
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- 3-phenyl-5,6-dihydrobenz(c)acridine-7-carboxylic acids and related compounds as cancer chemotherapeutic agents
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Dihydrobenz[c]acridine carboxylic acid derivatives are provided which are useful in treating tumors in mammals. These dihydrobenz[c]acridine carboxylic acid derivatives have the formula: STR1 or a pharmaceutically acceptable salt thereof, where R1/s
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- Nonconventional Friedel-Crafts Chemistry. 1. Reaction of α-Tetralone and Anthrone with Arenes under Friedel-Crafts Conditions
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α-Tetralone and anthrone were reacted with arenes in the presence of aluminum chloride to give 6-aryl-1-tetralone and 10-arylanthrone, respectively.The mechanism of these reactions are discussed.
- El-Zohry, Maher F.,El-Khawaga, Ahmed M.
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p. 4036 - 4039
(2007/10/02)
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