86-99-7Relevant articles and documents
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Cutler,Surrey
, p. 3394 (1950)
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Preparation method of hydroxychloroquine
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Paragraph 0114; 0125; 0127-0130, (2020/09/16)
The invention belongs to the technical field of medicine and chemical engineering, and particularly relates to a hydroxychloroquine preparation method. The method comprises: carrying out a condensation reaction on a quinoline intermediate 7-chloro-4-hydroxyquinoline sulfonate and a hydroxychloroquine side chain in a eutectic solvent to obtain a target product, wherein the preparation method of thequinoline intermediate 7-chloro-4-hydroxyquinoline sulfonate comprises the following steps: (1) by taking 4-chloro-2-nitrobenzoic acid as a raw material, carrying out a chlorination reaction to prepare acyl chloride, condensing the acyl chloride with Meldrum's acid, and hydrolyzing to obtain 4-chloro-2-nitroacetophenone; and (2) carrying out condensation reaction, nitro reduction cyclization andhydroxyl protection reaction on the 4-chloro-2-nitroacetophenone and N,N-dimethylformamide methylal to obtain the quinoline intermediate 7-chloro-4-hydroxyquinoline sulfonate. The method has the advantages of easily available raw materials, mild reaction conditions, difficulty in side reaction, avoidance of high-temperature production conditions, reduction of risks, good intermediate stability, high yield and good purity of the obtained hydroxychloroquine, and facilitation of large-scale production.
Preparation method 4-7 -dichloroquinoline (by machine translation)
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, (2020/10/20)
The method comprises the steps of: adding 4 chloroaniline and ethoxymethyl diethyl malonate as raw materials, carrying out decarboxylation reaction, carrying out decarboxylation through condensation, cyclization and hydrolysis, carrying out decarboxylation reaction, adding sulfuric acid to 7 - under 3 - pressure, 4 and washing to obtain solid 7 - hydroxyl 3 - chloroquinolines. 230 - 260 °C. The method comprises the following steps: carrying out decarboxylation reaction, adding sulfuric acid to reaction completely, layering, organic layer recovery and water layer reaction till 90 - 100 °C 6.0 - 6.5 kg reaction until reaction is complete 90 - 100 °C, layering, organic layer recovery and water layer reaction; and the steps and chlorination are carried out 150 -170 °C pH4 - 5 4 -7 . Reaction conditions are mild, yield is high, and quality is good. (by machine translation)
Synthesis, antituberculosis studies and biological evaluation of new quinoline derivatives carrying 1,2,4-oxadiazole moiety
Shruthi,Eswaran, Sumesh,Shivarudraiah, Prasad,Narayanan, Shridhar,Subramanian, Sangeetha
, p. 97 - 102 (2018/11/23)
Tuberculosis is the infectious disease caused by mycobacterium tuberculosis (Mtb), responsible for the utmost number of deaths annually across the world. Herein, twenty-one new substituted 1,2,4-oxadiazol-3-ylmethyl-piperazin-1-yl-quinoline derivatives were designed and synthesized through multistep synthesis followed by in vitro evaluation of their antitubercular potential against Mtb WT H37Rv. The compound QD-18 was found to be promising with MIC value of 0.5 μg/ml and QD-19 to QD-21 were also remarkable with MIC value of 0.25 μg/ml. Additionally, we have carried out experiments to confirm the metabolic stability, cytotoxicity and pharmacokinetics of these compounds along with kill kinetics of QD-18. These compounds were found to be orally bioavailable and highly effective. Altogether, these results indicate that QD-18, QD-19, QD-20 and QD-21 are promising lead compounds for the development of a novel chemical class of antitubercular drugs.