- Synthesis of [2,2’]Bifuranyl-5,5’-dicarboxylic Acid Esters via Reductive Homocoupling of 5-Bromofuran-2-carboxylates Using Alcohols as Reductants?
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Herein, we describe an environmentally benign and cost-effective protocol for the synthesis of valuable bifuranyl dicarboxylates, starting with α-bromination of readily accessible furan-2-carboxylates by LiBr and K2S2O8. Furthermore, the bromination intermediate product 5-bromofuran-2-carboxylates were then conducted in a palladium-catalyzed reductive homocoupling reactions in the presence of alcohols to afford bifuranyl dicarboxylates. One of the final products in this protocol, [2,2’]bifuran-5,5’-dicarboxylic acid esters, are essential monomers of poly(ethylene bifuranoate), which can be served as an green and versatile alternative polymer for traditional poly(ethylene terephthalate) that is currently common in technical plastics.
- Jiang, Huanfeng,Luo, Jiajun,Xie, Yi,Yin, Biaolin,Yu, Bin
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- NOVEL COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
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The present disclosure relates to a novel compound and a pharmaceutical composition comprising the same. The compound according to the present disclosure has effects for activating autophagy, and thus can be valuably used for preventing or treating diseas
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- Method for preparing 2,5-furandicarboxylic acid
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The invention discloses a method for preparing 2,5-furandicarboxylic acid. The method comprises the following steps: preparing the 2,5-furandicarboxylic acid by sequentially performing four-step reaction namely bromination reaction, esterification reaction, carbonylation reaction and hydrolysis reaction on furan-2-carboxylic acid, wherein a compound as shown in Formula 3, a compound as shown in Formula 4 and a compound as shown in Formula 5 are obtained by the bromination reaction, the esterification reaction and the carbonylation reaction respectively. Compared with the prior art, the invention can effectively solve the problem of not high yield or severe reaction condition requirement by improving the key overall process flow of the preparation method and reaction conditions of each step. The structural formulae of the compound as shown in Formula 3, the compound as shown in Formula 4 and the compound as shown in Formula 5 are as shown in the specification respectively.
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- Preparation method of ethyl 5-bromo-2-furoate
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The invention relates to a preparation method of ethyl 5-bromo-2-furoate. The preparation method comprises following steps: furoic acid and ethanol are mixed and stirred in a certain ratio, heated to 60-80 DEG C and subjected to refluxing until the components are completely dissolved, thionyl chloride is added proportionally and is dripped off within 1-4 h, a mixture is subjected to refluxing continuously for 5-8 h, and the reaction is ended; the mixture is subjected to rotary evaporation and concentration, and ethanol is recycled; remaining concentrate is diluted with water, extracted with n-hexane, washed with a weak base solution and a saturated salt solution, dried with anhydrous sodium sulfate and subjected to rotary evaporation and concentration, and a pure product of ethyl 5-bromo-2-furoate is obtained. The preparation method has the advantages as follows: reaction raw materials are relatively available, the price is reasonable, reaction conditions are mild, operation and control are easy, post-treatment is simple, and besides, the product is stable in quality and high in purity.
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Paragraph 0011
(2017/07/05)
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- Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles
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A total of 19 alkylated heterocycles (thiophenes, benzothiophenes, pyrroles, furans) were prepared (36-99% yield) from the respective pyridin-2-yl-substituted precursors employing alkylboronic acids as the C-H alkylating reagents in an oxidative (Ag2
- Wippich, Julian,Schnapperelle, Ingo,Bach, Thorsten
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supporting information
p. 3166 - 3168
(2015/06/11)
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- A diketopyrrolopyrrole molecule end-capped with a furan-2-carboxylate moiety: The planarity of molecular geometry and photovoltaic properties
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We designed and synthesized a diketopyrrolopyrrole (DPP) molecule with a fully-planar molecular geometry, 3,6-bis{5-[(ethylfuran-2-carboxylate)-2-yl] thiophene-2-yl}-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione (DPP(CF)2), for solution-processable organic solar cells (OSCs). It is theoretically calculated that the dihedral angles between the two furan-2-carboxylate end-groups and the DPP core are both only 0.56°. Due to this negligible steric distortion, the molecular conformation of DPP(CF) 2 can be considered fully coplanar, leading to a higher crystallinity for the DPP(CF)2 film. As a result, the hole mobility of DPP(CF)2 is one order of magnitude higher than that of the DPP derivative with thiophene-2-carboxylate as the end-group (DPP(CT)2). DPP(CF)2 exhibits both a low optical band gap (Eg) of 1.60 eV and a low-lying highest occupied molecular orbital (HOMO) energy level of -5.33 eV, implying that DPP(CF)2 is a promising electron donor for OSCs. OSCs with DPP(CF)2 or DPP(CT)2 as the electron donor and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the electron acceptor were fabricated. It is found that the DPP(CF) 2-based devices exhibit much better photovoltaic performance than the DPP(CT)2-based devices, with the highest power conversion efficiency of 5.37% and a short-circuit current density of 11.4 mA cm-2. This phenomenon can be ascribed to the superior charge-transporting ability of DPP(CF)2 due to its fully-planar molecular geometry. This journal is the Partner Organisations 2014.
- Fu, Lei,Fu, Weifei,Cheng, Pei,Xie, Zhixin,Fan, Congcheng,Shi, Minmin,Ling, Jun,Hou, Jianhui,Zhan, Xiaowei,Chen, Hongzheng
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p. 6589 - 6597
(2014/05/06)
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- HETEROCYCLIC DERIVATIVES AND THEIR USE IN TREATING HEPATITIS C
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Use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for use in treating or alleviating HCV, formula (I): wherein R1, R2, R4, Y1, Y2, Y3, A, B and W are as defined in the specification.
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Page/Page column 26-27
(2009/04/25)
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- C(4)-alkyl substituted furanyl cyclobutenediones as potent, orally bioavailable CXCR2 and CXCR1 receptor antagonists
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A novel series of cyclobutenedione centered C(4)-alkyl substituted furanyl analogs was developed as potent CXCR2 and CXCR1 antagonists. Compound 16 exhibits potent inhibitory activities against IL-8 binding to the receptors (CXCR2 Ki = 1 nM, IC50 = 1.3 nM; CXCR1 Ki = 3 nM, IC50 = 7.3 nM), and demonstrates potent inhibition against both Gro-α and IL-8 induced hPMN migration (chemotaxis: CXCR2 IC50 = 0.5 nM, CXCR1 IC50 = 37 nM). In addition, 16 has shown good oral pharmacokinetic profiles in rat, mouse, monkey, and dog.
- Chao, Jianhua,Taveras, Arthur G.,Chao, Jianping,Aki, Cynthia,Dwyer, Michael,Yu, Younong,Purakkattle, Biju,Rindgen, Diane,Jakway, James,Hipkin, William,Fosetta, James,Fan, Xuedong,Lundell, Daniel,Fine, Jay,Minnicozzi, Michael,Phillips, Jonathan,Merritt, J. Robert
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p. 3778 - 3783
(2008/02/10)
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- ISOTHIAZOLE DIOXIDES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of the formula (IA): and the pharmaceutically acceptable salts and solvates thereof. D and E are different groups wherein one is N and the other is CR50. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of formula IA.
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Page/Page column 314-315
(2010/02/13)
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- THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).
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Page 247; 345
(2008/06/13)
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- Heterocyclic indole derivatives and mono- or diazaindole derivatives
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There is provided a compound represented by the general formula (1): wherein Het represents an optionally substituted heterocyclic group; A1and A2each independently represent —CH═, etc.; A3represents —CH2—, etc.; R1represents a 4-fluorophenyl group, etc.; R2represents an alkyl group; n represents 0, 1 or 2, provided that when A1and A2both are —CH═, A3represents —CH2— or —SO2—, which is an indole derivative or a mono- or diazaindole derivative that has COX-2 inhibitory activity and is useful as a pharmaceutical, such as an anti-inflammatory agent, or addition salts thereof with a pharmaceutically acceptable acid or base, or hydrates thereof.
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Page column 53-54
(2008/06/13)
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- 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
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There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.
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- 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
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There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.
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- 3,4-DI-SUBSTITUTED CYCLOBUTENE-1, 2-DIONES AS CXC-CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of the formula (I)or a pharmaceutically acceptable salt or solvate thereof. Also disclosed is the treatment of chemokine-mediated diseases using compounds of the formula (II)
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- HETEROCYCLIC INDOLE DERIVATIVES AND MONO- OR DIAZAINDOLE DERIVATIVES
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Indole derivatives and mono- or diazaindole derivatives represented by general formula (1), pharmaceutically acceptable acid-addition salts or base-addition salts thereof or hydrates of the same which have a COX-2 inhibitory activity and are useful as drugs such as anti-inflammatory agents, wherein Het represents an optionally substituted heterocycle; A1 and A2 independently represent each -CH=, etc.; A3 represents -CH2-, etc.; R1 represents 4-fluorophenyl, etc.; R2 represents alkyl; and n is 0, 1 or 2, provided that when A1 and A2 are both -CH=, then A3 is -CH2- or -SO2-.
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- Ethynylheteroaromatic-acids having retinoic acid-like activity
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Retinoid-like activity is exhibited by compounds of the formula STR1 wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR 1 and its ketal derivatives where R 1 is --(CH 2) n CH 3 where n is defined above, or --CH 2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.
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