Application of cinchona alkaloid derivatives as cytotoxic compounds

A technology for cinchona alkaloids and drugs, which is applied in the directions of active ingredients of heterocyclic compounds, drug combinations, and medical preparations containing active ingredients, etc., can solve the problems of difficult, expensive and ineffective cancer treatment.

Inactive Publication Date: 2015-08-12
ADAM MICKIEWICZ UNIV
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  • Abstract
  • Description
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Problems solved by technology

Cancer treatment is difficult, expe

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  • Application of cinchona alkaloid derivatives as cytotoxic compounds
  • Application of cinchona alkaloid derivatives as cytotoxic compounds

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Experimental program
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Embodiment 1

[0040] Cinchonine (883 mg, 3 mmol) was dissolved in anhydrous DMF (12 mL), and the solution was then placed in an ice bath. The mixture was cooled to about 5°C and sodium hydride (50% NaH in mineral oil, 300 mg, 2 equiv) was added in portions over 0.5 h. The solution was stirred for 2 hours and an 80% solution of propargyl bromide in toluene (0.42 mL, 3.75 mmol, 1.25 equiv) was added using a syringe. The reaction mixture was allowed to stand overnight at room temperature. Next, dichloromethane (50 ml) was added to the reaction mixture, and the organic solution was washed successively with saturated NaCl solution (30 mL) and distilled water (30 mL). The organic layer was dried with anhydrous magnesium sulfate, then, the desiccant was filtered off, and the solvent was evaporated using a vacuum evaporator, keeping the temperature of the water bath in the range of 40-45°C. The crude product 9-oxo-propargyl cinchonine (PCN) was purified on a column packed with silica gel (60H, 0....

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Abstract

The subject matter of the invention is the application of 9-O-propargyl ethers of cinchona alkaloids of general formula represented by formula (1) wherein respective ethers have the following absolute configuration at C-8 and C-9 atoms: (8R,9S) –cinchonine configuration or (8S,9R) –cinchonidine configuration or (8R,9R) –9-epicinchonine configuration or (8S,9S) –9-epicinchonidine configuration for the manufacture of drugs used in cancer chemotherapy.

Description

technical field [0001] The subject of the present invention is the use of 9-O-propargylcinchonine for the preparation of medicaments for anticancer therapy. Background technique [0002] Cancer is one of the major health disorders reported in humans, with the highest mortality rate and increasing number of new cases, which above all relates to prolonged lifespan and lifestyle. Cancer treatment is difficult, expensive, and in most cases ineffective. Therefore, a new substance with cytostatic activity is urgently needed. They are often derived from natural products, especially from alkaloids and their derivatives, such as taxol, camptothecin or Vinca alkaloids (for reference, see Taglialatela-Scafati, O. Modern Alkaloids , Fattorusso E. (ed.), Wiley-VCH, 2007, p.25). Cinchona bark alkaloids, such as quinine, quinidine, cinchonidine and cinchonine, do not have specific antineoplastic properties. In experimental therapy for cancer diseases with multidrug resistance (MDR), co...

Claims

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Application Information

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IPC IPC(8): A61K31/49A61P35/00
CPCA61K31/4709A61K31/49A61P35/00
Inventor 勒奇·科勒维兹卡罗尔·卡克普扎克皮奥特·鲁兹可夫斯基
Owner ADAM MICKIEWICZ UNIV
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