3131-63-3Relevant academic research and scientific papers
Efficient cyclization of 2-phenoxyalkanals to 2-alkylbenzo[b]furans
Witczak,Kwiecien
, p. 2223 - 2230 (2005)
A new and efficient route to 2-alkylbenzo[b]furans via acid-catalyzed cyclization of 2-phenoxyalkanals under mild conditions over amberlyst-15 resin has been described. Copyright Taylor & Francis, Inc.
Photochromism of new diarylethene derivatives based on the hybrid photochromic skeleton of benzofuran and benzene moieties
Li, Hui,Pu, Shouzhi,Liu, Gang,Chen, Bing
, p. 15 - 24 (2014)
Four new photochromic diarylethenes with both benzofuran and benzene moieties were synthesized, and the structures of three diarylethenes were determined by single-crystal X-ray diffraction analysis. The six-membered benzene ring was connected directly to the central perfluorocyclopentene unit as an aryl moiety and available to participate in photoisomerization reaction. All the diarylethenes exhibit favorable photochromism and function as notable fluorescence switches in both hexane and poly(methyl methacrylate) films. The electron-donating substituents effectively enhanced the cyclization quantum yields, while the electron-withdrawing substituents notably shifted the fluorescent emission peaks to a longer wavelength in both solution and poly(methyl methacrylate) films. The result indicated that the different substituents linked at the reactive carbon atom of the benzene moiety had a significant effect on their optical and electrochemical properties.
NOVEL COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING SAME FOR ENHANCING ANTICANCER ACTIVITY
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Paragraph 0104-0105, (2021/11/04)
The present invention relates to a novel compound and a pharmaceutical composition for enhancing anticancer activity, which includes the same, and more particularly, to a pharmaceutical composition, which includes a compound represented by Formula 1 or a pharmaceutically acceptable salt thereof, thereby enhancing anticancer activity of an anticancer agent or radiation, and inducing proliferation inhibition and death of cancer cells, resulting in effectively treating cancer: In Formula 1, n is an integer of 0 to 4; R1 is hydrogen, C1 to C10 alkyl or aryl(C1 to C4)alkyl; R3 is C1 to C6 alkyl, and when there are a plurality of the R3, the R3s are the same or different; L1 is a direct bond, or C1 to C6 alkylene; R2 is hydrogen, C1 to C10 alkyl or aryl(C1 to C4)alkyl, and R4 is hydrogen, C1 to C4 alkyl, C3 to C8 cycloalkyl or aryl(C1 to C4)alkyl, or R2 and R4 are connected to form a 4 to 7-membered ring; and the alkyl of R1 to R4, the arylalkyl of R1, R2 and R4, the cycloalkyl of R4, the alkylene of L1 are each independently unsubstituted or substituted with a substituent such as a C1 to C6 alkyl group, a halo group, an aryl group, a haloalkyl group, a nitro group, a cyano group, an alkylthio group or an arylalkylthio group, and when the compound is substituted with a plurality of substituents, the substituents are the same or different.
Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents
Wen, Chang,Wu, Chuan,Luo, Ruiqiang,Li, Qinghan,Chen, Feng
, p. 3847 - 3861 (2021/07/02)
A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.
Preparation method of benzofuran compound
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Paragraph 0114-0117, (2019/04/04)
The invention relates to a preparation method of a benzofuran compound. The preparation method comprises the following steps: putting a furan compound, acetic acid and a Lewis acid catalyst in a reaction vessel, reacting for 0.5-24 h at 80-160 DEG C, and separating and purifying to obtain the benzofuran compound. According to the preparation method provided by the invention, the furan compound isused as a reaction raw material, an acetic acid water solution is used as a solvent, Lewis acid is used as a catalyst, and at a mild reaction temperature (80-160 DEG C), the benzofuran compound is directly obtained through one-step reaction. The preparation method provided by the invention can synthesize the benzofuran compound with a corresponding structure and functional groups based on the structure and functional groups of the furan compound as a raw material, the raw material components are simple , and the process is convenient to operate; wherein the selectivity of the obtained benzofuran is as high as 99% in the process of synthesizing benzofuran by using furan, so that the method has industrial application prospects.
Glutathione conjugation and protein adduction derived from oxidative debromination of benzbromarone in mice
Wang, Hui,Wang, Wenbao,Gong, Bowen,Wang, Zedan,Feng, Yukun,Zhang, Weige,Wang, Shaojie,Peng, Ying,Zheng, Jiang
, p. 1281 - 1290 (2019/11/20)
Benzbromarone (BBR), a uricosuric agent, has been known to induce hepatotoxicity, and its toxicity has a close relation to cytochrome P450-mediated metabolic activation. An oxidative debromination metabolite of BBR has been reported in microsomal incubations. The present study attempted to define the oxidative debromination pathway of BBR in vivo. One urinary mercapturic acid (M1) and one glutathione (GSH) conjugate (M2) derived from the oxidative debromination metabolitewere detected in BBR-treated mice after solid phase extraction.M1 andM2 shared the same chromatographic behavior and mass spectral identities as those detected in N-acetylcysteine/GSHand BBR-fortified microsomal incubations. The structure of M1 was characterized by chemical synthesis, along with mass spectrometry analysis. In addition, hepatic protein modification that occurs at cysteine residues (M93) was observed in mice given BBR. The observed protein adduction reached its peak 4 hours after administration and occurred in a dose-dependent manner. A GSH conjugate derived from oxidative debromination of BBR was detected in livers of mice treated with BBR, and the formation of the GSH conjugate apparently took place earlier than the protein adduction. In summary, our in vivo work provided strong evidence for the proposed oxidative debromination pathway of BBR, which facilitates the understanding of the mechanismsof BBR-induced hepatotoxicity. SIGNIFICANCE STATEMENT This study investigated the oxidative debromination pathway of benzbromarone (BBR) in vivo. One urinary mercapturic acid (M1) and one glutathione (GSH) conjugate (M2) derived from the oxidative debromination metabolite were detected in BBR-treated mice. M1 and M2 were also observed in microsomal incubations. The structure of M1 was characterized by chemical synthesis followed by mass spectrometry analyses. More importantly, protein adduction derived fromoxidative debromination ofBBR(M93) was observed in mice given BBR, and occurred in dose- and time-dependent manners. The success in detection of GSH conjugate, urinary N-acetylcysteine conjugate, and hepatic protein adduction in mice given BBR provided solid evidence for in vivo oxidative debromination of BBR. The studies allowed a better understanding of the metabolic activation of BBR.
A 2 - substituted benzofuran compound of the catalytic synthesis method
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Paragraph 0013; 0014; 0015, (2019/05/22)
The invention discloses a 2 - substituted benzofuran compound of the catalytic synthesis method, comprises the following steps: normal temperature and pressure, the 2 - alkynyl substituted phenol dissolved in acetonitrile, wherein the 2 - alkynyl substituted phenol with acetonitrile molar volume ratio of 1: 1mmol/mL, to obtain 2 - alkynyl substituted phenol acetonitrile solution; and then to the acetonitrile solution in adding cuprous chloride and cesium carbonate, wherein the cuprous chloride and cesium carbonate of respectively the molar consumption of 2 - alkynyl-substituted phenol mole amount of 5%; after, room temperature stirring 6 hours, produced by the reaction of 2 - substituted benzofuran compound. The invention 2 - substituted benzofuran compound of the catalytic method for synthesis of low cost, high yield, its preparation 1 g of 2 - substituted benzofuran compounds required the cost of the catalyst the prior by iridium catalyst is a catalyst of the synthetic method has lowered 2 orders of magnitude, to improve the yield of the 88.5 - 95.8%.
Ligand-Controlled Chemoselective C(acyl)-O Bond vs C(aryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings
Chatupheeraphat, Adisak,Liao, Hsuan-Hung,Srimontree, Watchara,Guo, Lin,Minenkov, Yury,Poater, Albert,Cavallo, Luigi,Rueping, Magnus
supporting information, p. 3724 - 3735 (2018/03/21)
A ligand-controlled and site-selective nickel catalyzed Suzuki-Miyaura cross-coupling reaction with aromatic esters and alkyl organoboron reagents as coupling partners was developed. This methodology provides a facile route for C(sp2)-C(sp3) bond formation in a straightforward fashion by successful suppression of the undesired β-hydride elimination process. By simply switching the phosphorus ligand, the ester substrates are converted into the alkylated arenes and ketone products, respectively. The utility of this newly developed protocol was demonstrated by its wide substrate scope, broad functional group tolerance and application in the synthesis of key intermediates for the synthesis of bioactive compounds. DFT studies on the oxidative addition step helped rationalizing this intriguing reaction chemoselectivity: whereas nickel complexes with bidentate ligands favor the C(aryl)-C bond cleavage in the oxidative addition step leading to the alkylated product via a decarbonylative process, nickel complexes with monodentate phosphorus ligands favor activation of the C(acyl)-O bond, which later generates the ketone product.
Copper-catalyzed direct alkylation of heteroarenes
Theunissen, Cédric,Wang, Jianjun,Evano, Gwilherm
, p. 3465 - 3470 (2017/07/11)
An efficient and broadly applicable process is reported for the direct alkylation of C-H bonds in heteroarenes, privileged scaffolds in many areas of science. This reaction is based on the copper-catalyzed addition of alkyl radicals generated from activated secondary and tertiary alkyl bromides to a wide range of arenes, including furans, thiophenes, pyrroles, and their benzo-fused derivatives, as well as coumarins and quinolinones.
Compound for treatment or prevention of hyperuricemia or gout
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Paragraph 0061; 0062, (2017/01/26)
The invention discloses a compound for treatment or prevention of hyperuricemia or gout. The compound is the compound shown as formula (I) or formula (II) or pharmaceutical acceptable salts thereof. The compound or its pharmaceutical acceptable salts can be applied to urate excretion promotion so as to treat or prevent hyperuricemia or gout. (formula (1), formula (II)).
