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Dihydroartemisinin diploid derivative, and medicine composition and application thereof

A technology of dihydroartemisinin and derivatives, applied in the field of medicine, can solve the problems of no diploid amphiphilic molecules of artemisinin, poor water solubility of artemisinin, dihydroartemisinin, and artesunate , to achieve a good effect of killing malaria parasites and a good anti-tumor effect

Active Publication Date: 2017-07-07
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some new drugs appeared after the middle of the 20th century. Artemisinin and dihydroartemisinin developed by Chinese scientists have good anti-malarial effects, but the water-soluble drugs of artemisinin, dihydroartemisinin and artesunate very poor sex
But so far there is no report of artemisinin diploid amphiphile molecules, and there is no report on the assembly of artemisinin diploid amphiphile molecules into nanoparticles

Method used

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  • Dihydroartemisinin diploid derivative, and medicine composition and application thereof
  • Dihydroartemisinin diploid derivative, and medicine composition and application thereof
  • Dihydroartemisinin diploid derivative, and medicine composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] Synthesis of dihydroartemisinin diploid phosphatidylcholine (see the synthetic route figure 2 )

[0132] Dissolve artesunate 0.128g, CDI 0.162g in 15mL dichloromethane, react at room temperature for 4 hours, spin dry to remove dichloromethane, dissolve the residue in dimethyl sulfoxide 10mL, add glycerophosphorylcholine 0.026g, DBU 0.05 g, react overnight at 40°C. The product is purified with a flash preparative chromatography system (chromatographic column: silica gel, eluent: dichloromethane / methanol), and the product is a white solid with a yield of 35%. The purity is 97.3% as detected by high performance liquid chromatography, and the solubility in water at 20°C It is 16.96g / L (artesunate is only 0.36g / L). Mass Spectrum (MS) (m / z): [M+Na] + 1012.42. 1 H-NMR (500MHz, DMSO-d 6 )See image 3 : δ5.67(d,J=8.3Hz,2H,H-10,10'),5.55(s,2H,H-12,12'),4.29–4.10(m,1H,H-20),4.03 -3.75(m,4H,H-21,22),3.51-3.47(m,4H,H-23,24),3.13(s,9H,H-25,26,27),2.72-2.54(m, 8H,H-18,18',17,...

Embodiment 2

[0134] Synthesis of dihydroartemisinin dithiodiacetic acid diploid phosphatidylcholine (see the synthetic route image 3 )

[0135] 1.5 g of dihydroartemisinin and 1 g of dithiodiacetic anhydride were dissolved in 20 mL of chloroform, 0.5 g of triethylamine was added, and the reaction was stirred overnight at 40°C. The solvent was removed, and the flash preparative chromatography system was used for separation and purification (chromatographic column: silica gel, eluent: dichloromethane / methanol), and the product dihydroartemisinin dithiodiacetic acid was obtained as a white solid 1.8g.

[0136] Dihydroartemisinin dithiodiacetic acid is 0.5g of white solid, 0.3g of CDI is dissolved in 15mL of dichloromethane, reacted at room temperature for 3 hours, spin-dried to remove dichloromethane, the residue is dissolved in 10mL of dimethyl sulfoxide, Add 0.12 g of glycerophosphorylcholine and 0.3 g of DBU, and react overnight at 40°C. The product was purified with a flash preparative...

Embodiment 3

[0139] Synthesis of dihydroartemisinin dithiodiacetic acid diploid carboxybetaine (see the synthetic route Figure 4 )

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Abstract

The invention discloses a dihydroartemisinin diploid derivative, and a medicine composition and application thereof. The derivative is artemisinin diploid, and is applied to a medicine for treating or preventing malaria caused by plasmodium, a medicine for treating autoimmune diseases such as lupus erythematosus, and an antitumor medicine; the medicine composition is prepared from the dihydroartemisinin diploid derivative and a pharmaceutically acceptable carrier.

Description

technical field [0001] The invention relates to a diploid derivative of dihydroartemisinin, its pharmaceutical composition and its application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Parasitic diseases are diseases caused by parasites invading the human body. The pathological changes and clinical manifestations caused by different insect species and parasitic sites are different. This type of disease is widely distributed and can be seen all over the world. It is more common in poor and backward areas with poor sanitation, and more in tropical and subtropical areas. The infected people are mainly working people who have more contact with the source of the epidemic and those with low immunity. child. [0003] Malaria is the most important parasitic disease in tropical areas, and it is also an infectious disease caused by Plasmodium parasites in humans. Patients are infected by the bite of an Anopheles mosquito or the blood t...

Claims

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Application Information

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IPC IPC(8): C07F9/655C07D519/00A61K31/685A61K31/357A61K9/127A61P33/12A61P33/06A61P33/02A61P29/00A61P19/02A61P31/22A61P37/02A61P7/06A61P5/18A61P1/00A61P35/00A61P35/02A61P17/00A61P33/00
CPCA61K9/127C07D519/00C07F9/65522A61P17/06A61P19/02A61P33/06A61P35/00C07F9/6561Y02A50/30C07F9/65525
Inventor 李新松司马凌龙兵
Owner SOUTHEAST UNIV
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