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Quinoline-1, 2, 4-triazine heterozygote as well as preparation method and application thereof

A hybrid, quinoline technology, applied to quinoline-1, can solve problems such as hindering the elimination of malaria, and achieve the effect of good antimalarial effect

Active Publication Date: 2022-03-04
JIANGSU OCEAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the long-term use of antimalarial drugs, Plasmodium falciparum has successively developed resistance to antimalarial drugs chloroquine, antifolate (sulfadoxine-pyrimethamine) and artemisinin, and has spread around the world, hindering Malaria Elimination

Method used

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  • Quinoline-1, 2, 4-triazine heterozygote as well as preparation method and application thereof
  • Quinoline-1, 2, 4-triazine heterozygote as well as preparation method and application thereof
  • Quinoline-1, 2, 4-triazine heterozygote as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0062] The preparation method of the compound shown in formula II takes following method:

[0063]

[0064] Reaction of 4,7-dichloroquinoline with diamines (C1, C2 and C5): Weigh 4,7-dichloroquinoline (5.05mmol) and dissolve it in 20mL of absolute ethanol, add diamine (15.15mmol) and mix well , heated and stirred at 110°C, refluxed for 12-18 hours, TLC monitored the end of the reaction, stopped the reaction, waited for the reaction system to cool down to room temperature, removed absolute ethanol by rotary evaporation under reduced pressure, added ethyl acetate and saturated saline for extraction, and took the upper organic Anhydrous sodium sulfate was added to the phase to remove water, and then the organic phase liquid was evaporated and dried under reduced pressure with a rotary evaporator to obtain a crude product, which was separated and purified by silica gel column chromatography to obtain the product.

[0065] Reaction of 4,7-dichloroquinoline with alcohol amine (C3...

Embodiment 1

[0072] Embodiment 1: Preparation of N1-(7-chloroquinolin-4-yl)-N3-(1,2,4-triazin-3-yl)propane-1,3-diamine

[0073]

[0074] Take a 50mL flask, accurately weigh 4,7-dichloroquinoline (5.05mmol) into the flask, add 20mL of absolute ethanol and stir until dissolved, add 1,3 propylenediamine (15.15mmol) and mix evenly, heat and stir at 90°C , reflux reaction for 12 hours, TLC monitors the end of the reaction, stop the reaction, wait for the reaction system to drop to room temperature, remove absolute ethanol by rotary evaporation under reduced pressure, add ethyl acetate and saturated brine for extraction, take the upper organic phase and add anhydrous sodium sulfate to dry and remove water, and then use a rotary evaporator to remove ethyl acetate under reduced pressure to obtain a solid crude product, which was separated and purified by silica gel column chromatography (eluent: dichloromethane:methanol=20:1) to obtain intermediate II.

[0075] Take a 250mL flask, weigh 3-methy...

Embodiment 2

[0077] Example 2: Preparation of N1-(7-chloroquinolin-4-yl)-N4-(1,2,4-triazin-3-yl)butane-1,4-diamine

[0078]

[0079] The preparation method refers to Example 1. A white solid was obtained, yield 50.6%, m.p.157-159°C, 1 H NMR (500MHz, Methanol-d 4 )δ8.45(d, J=2.2Hz, 1H), 8.35(d, J=5.7Hz, 1H), 8.22(d, J=2.2Hz, 1H), 8.11(d, J=9.0Hz, 1H) ,7.78(d,J=2.1Hz,1H),7.40(dd,J=9.0,2.2Hz,1H),6.54(d,J=5.7Hz,1H),3.52(t,J=6.6Hz,2H) ,3.44(t,J=6.7Hz,2H),1.90–1.77(m,4H). 13 C NMR (126MHz, Methanol-d 4 )δ151.43, 150.79, 150.54, 148.05, 139.77, 134.99, 129.44, 129.43, 125.99, 124.58, 122.94, 117.33, 98.25, 42.30, 25.25

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Abstract

The invention relates to the technical field of medicinal chemistry, in particular to a quinoline-1, 2, 4-triazine heterozygote as well as a preparation method and application thereof. The structure of the chloro-quinoline and 1, 2, 4-triazine heterozygote is as shown in a formula I in the specification. The preparation method of the quinoline-1, 2, 4-triazine heterozygote comprises the following step of: reacting a compound shown as a formula II with a compound shown as a formula III in the presence of sodium carbonate or cesium carbonate to obtain the quinoline-1, 2, 4-triazine heterozygote. The quinoline-1, 2, 4-triazine heterozygote disclosed by the invention has very good antimalarial activity.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a quinoline-1,2,4-triazine hybrid, a preparation method and an application thereof. Background technique [0002] Malaria is a disease that threatens human life. Traditional malaria treatment drugs mainly include plant extracts such as quinine and artemisinin. On this basis, artemisinin, dihydroartemisinin, artemether, chloroquine, and Primeraquine, etc., is an important drug in the treatment of malaria at present. However, with the long-term use of antimalarial drugs, Plasmodium falciparum has successively developed resistance to antimalarial drugs chloroquine, antifolate (sulfadoxine-pyrimethamine) and artemisinin, and has spread around the world, hindering Elimination of malaria. [0003] There are only a handful of new antimalarial drugs currently in the clinical research stage. Obviously, it is imminent to develop new antimalarial drugs with new modes of action...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D401/14A61P33/06
CPCC07D401/12C07D401/14A61P33/06Y02A50/30
Inventor 史大华冯媛媛董常娥苏佳镔刘玉委钱晶晶刘珊鸣邹靖培
Owner JIANGSU OCEAN UNIV
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