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Substituted quinoline-2-formaldehyde-phenylhydrazone derivative, and preparation method and application thereof

A compound, quinoline technology, applied in the fields of medicinal chemistry and pharmacotherapeutics, which can solve the problems of insignificant experimental effects and other problems

Inactive Publication Date: 2012-10-17
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the existing antiviral drugs are effective against DV in vitro tests, the effects of in vivo tests are not obvious

Method used

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  • Substituted quinoline-2-formaldehyde-phenylhydrazone derivative, and preparation method and application thereof
  • Substituted quinoline-2-formaldehyde-phenylhydrazone derivative, and preparation method and application thereof
  • Substituted quinoline-2-formaldehyde-phenylhydrazone derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1 Preparation of 2-methyl-quinoline-4-carboxylic acid (intermediate II)

[0073]

[0074] Under the protection of nitrogen, 1.0 grams of isatin was put into potassium hydroxide solution (potassium hydroxide: 2.67 grams, water: 5 milliliters), reflux reaction at 50 ° C for 15 hours, 5 ml of acetone was added dropwise, and the reaction was completed for 3 hours. The reaction solution was cooled to room temperature, adjusted to pH=7 with concentrated hydrochloric acid, and a small amount of potassium chloride solid was formed, which was removed by suction filtration. Then the pH of the mother liquor was adjusted to 3, and a large amount of milky white solid was precipitated, which was suction filtered, washed with water, and dried to obtain intermediate II as a white solid with a yield of 50%. Mp 248-250°C; 1 H NMR (DMSO, 400MHz): δ2.72(s, 3H), 7.64(t, 1H), 7.78(t, 1H), 7.84(s, 1H), 8.02(d, 1H), 8.63(d, 1H ).

Embodiment 2

[0075] Example 2 Preparation of ethyl 2-methyl-quinoline-4-carboxylate (intermediate III)

[0076]

[0077] Put 1.0 g of 2-methyl-4-quinolinecarboxylic acid (intermediate II) into 30 ml of ethanol, add 2 ml of concentrated sulfuric acid dropwise, mix and stir at 80° C. for 18 hours, and evaporate the solvent to obtain 0.86 g of 2-methanol Ethyl-4-quinolinecarboxylate (Intermediate III) is a white solid with a yield of 80%. 1 H NMR (CDCl 3 , 400MHz) δ1.50(t, 3H), 2.83(s, 3H), 4.53(q, 2H), 7.61(t, 1H), 7.76(t, 1H), 7.82(s, 1H), 8.10(d , 1H), 8.71(d, 1H).

Embodiment 3

[0078] Example 3 Preparation of ethyl 2-formyl-quinoline-4-carboxylate (intermediate IV)

[0079]

[0080] Put 0.50 g of ethyl 2-methyl-4-quinolinecarboxylate (intermediate III) into 10 ml of dioxane solution, add 1.30 g of selenium dioxide, and react under reflux for 4 hours. After the reaction, dioxane was distilled off, extracted with ethyl acetate and water, the ester layer was washed with water, washed with brine, dried, concentrated, and column chromatographed to obtain ethyl 2-formyl-4-quinolinecarboxylate (intermediate VI), yield 99%. 1 H NMR (CDCl 3 , 400MHz): δ1.52(t, 3H), 4.56(q, 2H), 7.83(t, 1H), 7.91(t, 1H), 8.35(d, 1H), 8.54(s, 1H), 8.90( d, 1H), 10.29(s, 1H).

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PUM

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Abstract

The present invention relates to a substituted-quinoline-2-formaldehyde-phenylhydrazone derivative and a preparation method and application thereof, and in particular relates to a novel 4-acyl-quinoline-2-formaldehyde-phenylhydrazone derivative, and a preparation method and application thereof to preparation of therapeutic drugs for dengue fever and dengue hemorrhagic fever caused by dengue virus. A structure of the compound is shown as a formula 1. The compound can be used as a protease inhibitor for a dengue virus NS2B-NS3, so as to block further proliferation of the dengue virus in a host.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, and more specifically relates to substituted quinoline-2-formaldehyde-phenylhydrazone compounds and a preparation method thereof. The compound can be used for treating diseases caused by dengue virus (DV, Dengue virus). Background technique [0002] Dengue virus is an important member of the dengue subgroup of the flavivirus genus of the family Flaviviridae. It is a single-stranded RNA virus, infectious, and basic capsid protein c to form the nucleocapsid of the virus. Dengue virus existing in nature can be divided into four serotypes, namely DEN-1, DEN-2, DEN-3 and DEN-4, and there are antigenic cross-reactions between different serotypes. It can cause mild dengue fever (DF, Dengue fever) and extremely severe dengue hemorrhagic fever / dengue shock syndrome (DHF / DSS, Dengue hemorrhagic fever / Dengue shock syndrome). Its vectors are Aedes aegypti and Aedes albopictus, ...

Claims

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Application Information

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IPC IPC(8): C07D215/50A61K31/635A61K31/47A61P31/14
CPCY02A50/30
Inventor 朱维良李剑杨财广唐炜邓菁李宁刘洪川冯春兰左建平左之利罗小民蒋华良陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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