- Synthesis method and device of 4 -hydroxyquinoline -3 - formic acid
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The invention relates to the technical field of medicine preparation, and particularly discloses a synthesis method and device of 4 -hydroxyquinoline -3 - formic acid, wherein o-nitrobenzoic acid and a monoethyl propionate potassium salt are condensed to obtain 3 - (2 - nitrophenyl) -3 - oxopropanoate. The ethyl powder is reacted with 3 - (2 - nitrophenyl) -3 - oxopropanoate to obtain 3 - (2 - aminophenyl) -3 - oxopropanoate. 3 - (2 - Aminophenyl) -3 - oxopropanoate was reacted with DMF-DMA and DMF via a closed loop to give 4 -hydroxyquinoline -3 - ethyl ester. The 4 -hydroxyquinoline -3 - formate was hydrolyzed under basic conditions to give 4 -hydroxyquinoline -3 - formic acid. 4 -hydroxyquinoline -3 - formic acid has the advantages of low cost, short reaction time and simple post-treatment in the synthesis process.
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Paragraph 0096-0101; 0112
(2021/09/21)
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- Combining 1,3-Ditriazolylbenzene and Quinoline to Discover a New G-Quadruplex-Interactive Small Molecule Active against Cancer Stem-Like Cells
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Quadruplex nucleic acids are promising targets for cancer therapy. In this study we used a fragment-based approach to create new flexible G-quadruplex (G4) DNA-interactive small molecules with good calculated oral drug-like properties, based on quinoline
- Mendes, Eduarda,Cadoni, Enrico,Carneiro, Filipa,Afonso, Marta B.,Brito, Hugo,Lavrado, Jo?o,dos Santos, Daniel J. V. A.,Vítor, Jorge B.,Neidle, Stephen,Rodrigues, Cecília M. P.,Paulo, Alexandra
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supporting information
p. 1325 - 1328
(2019/06/21)
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- Preparation method of 4-hydroxyquinoline-3-carboxylic acid
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The invention relates to the technical field of organic synthesis and bulk drug intermediates, and concretely relates to a preparation method of a key intermediate 4-hydroxyquinoline-3-carboxylic acid of a new medicine ivacaftor for treating cystic fibrosis. The preparation method comprises the following steps: 1, carrying out a condensation reaction: reacting o-nitrobenzoic acid, potassium monoethyl malonate and N,N-carbonyldiimidazole to prepare ethyl 3-(2-nitrophenyl)-3-oxopropanoate; 2, carrying out a reduction reaction: carrying out catalytic hydrogenation reduction on ethyl 3-(2-nitrophenyl)-3-oxopropanoate to prepare ethyl 3-(2-aminophenyl)-3-oxopropanoate; 3, carrying out a cyclization reaction: carrying out nucleophilic addition and cyclization reaction on ethyl 3-(2-aminophenyl)-3-oxopropanoate and N,N-dimethyl formamide dimethyl acctel to obtain ethyl 4-hydroxyquinoline-3-carboxylate; and 4, carrying out a hydrolysis reaction: carrying out the hydrolysis reaction on ethyl 4-hydroxyquinoline-3-carboxylate to obtain 4-hydroxyquinoline-3-carboxylic acid. The preparation method has the advantages of easily available raw materials, mild reaction conditions, simplicity and convenience in post-treatment, suitableness for amplified preparation, and high yield.
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Paragraph 0015; 0048; 0049; 0050; 0051; 0052; 0053
(2017/02/09)
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- COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
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The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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- Dichloro-4-quinolinol-3-carboxylic acid: Synthesis and antioxidant abilities to scavenge radicals and to protect methyl linoleate and DNA
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5,7-, 5,8-, 6,8-, 7,8-Dichloro-4-quinolinol-3-carboxylic acid (5,7-, 5,8-, 6,8-, 7,8-DCQA) together with 7-chloro-4-quinolinol-3-carboxylic acid (7-CQA) and 4-quinolinol-3-carboxylic acid (QA) were synthesized to investigate the antioxidant properties. 5,7-DCQA exhibited the highest ability to scavenge 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2′-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl radicals. 6,8-DCQA possessed the highest efficacy to protect methyl linoleate against 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH)-induced oxidation. 5,7-, 5,8-DCQA and QA were able to retard the β-carotene-bleaching in β-carotene-linoleic acid emulsion. In addition, 5,8- and 6,8-DCQA efficiently protected DNA against hydroxyl radical (.OH)-mediated oxidation, and 5,8-DCQA and 7-CQA were active to protect DNA against AAPH-induced oxidation. Furthermore, only 7-CQA can protect DNA against Cu2+/glutathione (GSH)-mediated oxidation. Dichloro-4-quinolinol-3-carboxylic acids were potent to be antiradical drugs, and were worthy to be researched pharmacologically.
- Li, Guo-Xiang,Liu, Zai-Qun,Luo, Xu-Yang
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experimental part
p. 1821 - 1827
(2010/06/21)
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- Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors
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Thirty-two quinoline derivatives were designed and synthesized as HIV-1 Tat-TAR interaction inhibitors. All the compounds showed high antiviral activities in inhibiting the formation of SIV-induced syncytium in CEM174 cells. Nine of them with low cytotoxicities were evaluated by Tat dependent HIV-1 LTR-driven CAT gene expression colorimetric enzyme assay in human 293T cells, indicating effective inhibitory activities of blocking the Tat-TAR interaction. Molecular modeling experiments indicated that these compounds may inhibit Tat-TAR interaction by binding to Tat protein instead of TAR RNA.
- Chen, Shuguang,Chen, Ran,He, Meizi,Pang, Ruifang,Tan, Zhiwu,Yang, Ming
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experimental part
p. 1948 - 1956
(2009/05/26)
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- Syntheses and photochromic behavior of biquinolinium salts
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Three isomers of N,N′-dibenzy-biquinolinium dibromide were synthesized and their photoinduced coloration properties were investigated in the thin poly(N-vinylpyrrolidone) films. Upon photo-irradiation, the colorless film of 4,4′-biquinolinium salt became
- Nanasawa,Tomoda,Hirai
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p. 163 - 168
(2007/10/03)
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- 4-HYDROXY-2-QUINOLONES. 20. SYNTHESIS AND CHEMICAL CONVERSIONS OF ETHYL ESTERS OF CHLORO-SUBSTITUTED QUINOLINE-3-CARBOXYLIC ACIDS
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Preparative methods for the synthesis of ethyl esters of 2,4-dichloro- and 2-oxo-4-chloroquinoline-3-carboxylic acids were developed.The behavior of the compounds indicated was studied under conditions of alkaline and acidic hydrolysis, in reactions with some nucleophilic reagents, as well as in reductive dehalogenation.Results of the study of the antimicrobial and antiinflammatory activity of the synthesized compounds are presented.
- Ukrainets, I. V.,Taran, S. G.,Gorokhova, O. V.,Marusenko, N. A.,Kovalenko, S. N.,et al.
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p. 167 - 175
(2007/10/03)
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