- Copper-catalyzed hydrolysis of bromoisoquinolines: Preparation of hydroxyisoquinolines
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A complex phenomenon was observed in the process of preparing hydroxyisoquinoline through copper-catalyzed hydrolysis of bromoisoquinoline. The copper (II) complexes of hydroxyisoquinoline (L2Cu.5H2O) were characterized by high resolution mass spectra, thermogravimetric analysis, IR, 1H nuclear magnetic resonance (NMR), and 2D-NMR. The Cu (II) complexes were mononuclear and coordinated with oxygen and nitrogen atom of two hydroxyisoquinoline and five water molecules in which a strong hydrogen bond was present. Two optimized methods had been studied to prevent the formation of copper (II) complexes. The isoquinoline with 4, 5, 6, 7, and 8 hydroxyl substitutions were successfully prepared by copper-catalyzed hydrolysis of corresponding bromoisoquinoline and then workup by sodium sulfide or adjusted pH by dry ice or carbon dioxide gas.
- Xingjun, Jiang,Jianbo, He,Hongli, Chen,Weiqing, Yang,Yuanyuan, Zhang,Menglin, Ma
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- Synthetic method of 8-isoquinolinol
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The invention discloses a synthetic method of 8-isoquinolinol, and belongs to the field of synthesis method of isoquinoline compounds. The synthetic method comprises following steps: 8-chloroisoquinoline, copper acetylacetonate, lithium hydroxide monohydrate, and ligand 1,3-bis(4-hydroxyl-2,6-dimethyl phenyl)urea are added into a mixed solution of dimethyl sulfoxide and water; under nitrogen protection, an obtained reaction solution is subjected to heating with stirring until reaction is completed, and pH value is adjusted to 5 with HCl after cooling; an obtained mixed liquid is extracted with ethyl acetate, an obtained organic phase is washed with saturated salt solution, is dried with anhydrous sodium sulfate, and then is subjected to spin drying; and an obtained crude product is subjected to column chromatography separation so as to obtain 8-isoquinolinol. According to the synthetic method, 8-chloroisoquinoline is taken as a raw material; synthesis route is simple; the synthetic method is reasonable; the raw materials are easily available; operation and subsequent treatment are convenient; total yield is as high as 72%; amplify production is convenient to realize; and large-scale production of 8-isoquinolinol can be realized.
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Paragraph 0016; 0018-0019
(2017/08/29)
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- AZACYCLIC COMPOUNDS AS INHIBITORS OF SENSORY NEURONE SPECIFIC CHANNELS
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Compounds of the formula (I), and pharmaceutically acceptable salts thereof, are found to be antagonists of SNS sodium channels. They are therefore useful as analgesic and neuroprotective agents wherein: X is -N- or -CH-; n is from 0 to 3.
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- Studies on anti-Helicobacter pylori agents. Part 1: Benzyloxyisoquinoline derivatives
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The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of benzyloxyisoquinoline derivatives that was discovered by a random screening process, are described. In the in vitro assay, compound 10c containing a 3-acetamido-2,6-dichlorobenzyl substituent was found to have extremely potent activity against H. pylori and no activity against other common bacteria. The anti-H. pylori activity of 10c was superior to that of amoxicillin (AMPC) (1) and clarithromycin (CAM) (2). However, 10c did not show in vivo efficacy in a mouse infection model; a feature attributed to the lack of strong bactericidal activity at short contact times. (C) 1999 Elsevier Science Ltd.
- Yoshida, Yoshiki,Barrett, David,Azami, Hidenori,Morinaga, Chizu,Matsumoto, Satoru,Matsumoto, Yoshimi,Takasugi, Hisashi
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p. 2647 - 2666
(2011/05/18)
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- Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4
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Biotransformation of quinoline, isoquinoline, quinoxaline and quinazoline using growing cultures of Pseudomonas putida UV4 yielded cis-dihydro diols from the oxidation of the carbocyclic aromatic ring.Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings.Ring cleavage of the quinoline skeleton to yield anthranilic acid, and cis-diol formation (with alkene bond reduction) to yield cis-5,6,7,8-tetrahydroquinazoline-5,6-diol from quinazoline were observed.The cis-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxaline (5,6-) were found to be optically pure, while metabolism of isoquinoline gave on e homochiral (5,6-) and one racemic 7,8-) cis-dihydro diol product.The absolute configuration of the cis-dihydro diol metabolites have been determined using 1H NMR analyses, stereochemical correlations and X-ray crystallography methods.
- Boyd, Derek R.,Sharma, Narain D.,Dorrity, Michael R. J.,Hand, Mark V.,McMordie, R. Austin S.,et al.
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p. 1065 - 1072
(2007/10/02)
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