- Preparation method of benzbromarone
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The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of benzbromarone. According to the method disclosed by the invention, polystyrene-loaded aluminum trichloride is used as a catalyst to carry out Friedel-Crafts acylation reaction, so that the catalytic effect is good, and the catalyst can be recycled, in the demethylation reaction process, aluminum trichloride is adopted to replace common pyridine hydrochloride, so that the reaction temperature can be reduced, and the yield can be increased, in the bromination reaction, sodium sulfide and hydrogen peroxide are adopted to replace bromine, so that the technical problems of strong corrosivity of bromine, great harm to human bodies and environmental pollution are solved, and meanwhile, the yield can be further improved.
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Paragraph 0023; 0028-0029; 0032; 0037-0038; 0041; 0046-0047
(2021/03/11)
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- Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds
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2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.
- Huang, Wenbo,Xu, Jing,Liu, Changhui,Chen, Zhiyan,Gu, Yanlong
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p. 2941 - 2950
(2019/02/26)
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- DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION
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A compound represented by the general Formula (I): a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A - K are individually selected from carbon or nitrogen; X = -O, -NR1,or -S; R1-11 are individually selected from the group consisting of-H, C1-C6 alkyl, C6-C aryl, substituted C6-C14 aryl, C1-C14-alkoxy, halogen, hydroxyl, carboxy, cyano, C1-C6-alkanoyloxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, trifluoromethyl, hydroxy, C2-C6-alkoxycarbonyl, C2-C6-alkanoylamino, -O-R12, S-R12,-SO2-Ri2, -NHSO2R12 and -NHCO2R12, wherein R12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C1-C6-alkyl, C6-C10 aryl,C1-C6-alkoxy and halogen, and C4-C20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.
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- Developing potent human uric acid transporter 1 (hURAT1) inhibitors
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The kidneys are a vital organ in the human body. They serve several purposes including homeostatic functions such as regulating extracellular fluid volume and maintaining acid-base and electrolyte balance and are essential regarding the excretion of metabolic waste. Furthermore, the kidneys play an important role in uric acid secretion/reabsorption. Abnormalities associated with kidney transporters have been associated with various diseases, such as gout. The current study utilized Xenopus oocytes expressing human uric acid transporter 1 (hURAT1; SLC22A12) as an in vitro method to investigate novel compounds and their ability to inhibit 14C-uric acid uptake via hURAT1. We have prepared and tested a series of 2-ethyl-benzofuran compounds and probed the hURAT1 in vitro inhibitor structure-activity relationship. As compared to dimethoxy analogues, monophenols formed on the C ring showed the best in vitro inhibitory potential. Compounds with submicromolar (i.e., IC 50 1000 nM) inhibitors were prepared by brominating the corresponding phenols to produce compounds with potent uricosuric activity.
- Wempe, Michael F.,Jutabha, Promsuk,Quade, Bettina,Iwen, Timothy J.,Frick, Morin M.,Ross, Ian R.,Rice, Peter J.,Anzai, Naohiko,Endou, Hitoshi
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experimental part
p. 2701 - 2713
(2011/06/25)
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- Process for the preparation of 3-benzoyl benzofuran derivatives
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The invention relates to a process for the preparation of 3-benzoyl benzofuran derivatives of general formula: STR1 wherein a benzofuran derivative of general formula: STR2 is reacted in situ in the presence of aluminium chloride successively with phosgene or oxalyl chloride, and then with a phenolic derivative of general formula: STR3 to produce a complex which is hydrolysed to form the desired compound of 3-benzoyl benzofuran.
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- Preparation of 2-alkyl-3-(4-hydroxybenzoyl)benzofuran
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The invention relates to new molecular complexes of general formula: STR1 in which R represents a straight- or branched-chain alkyl radical having from 1 to 4 carbon atoms and R1 represents one of the radicals: STR2 These molecular complexes are especially useful for the preparation of 2-alkyl-3-(4-hydroxybenzoyl)benzofurans.
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- Pharmaceutical compositions and methods of producing coronary vasodilation
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Pharmaceutical compositions and methods of producing coronary vasodilation by administering substituted benzofurans, for example 2-n-butyl-3-[4' -(2-hydroxy-3-isopropylamino)propoxybenzoyl] benzofuran.
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