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Technology for producing cytarabine through chemical synthesis method

A chemical synthesis method and cytarabine technology, which is applied in the field of synthesis technology of organic compounds, can solve the problems of high cost of cytarabine, many reaction steps, and many reagents involved, and achieves toxicity, easy recycling, and production. Low cost, stable and controllable quality

Inactive Publication Date: 2011-01-19
HENAN NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has many steps and low yield
[0029] In short, there have been many reports on the chemical synthesis methodology of cytarabine and the biomimetic synthesis method under chemical conditions at home and abroad. The industrial production of cytarabine is also produced by enterprises in many countries, but there are many Insufficient, mainly because there are many reaction steps, many reagents involved or expensive price, and low yield, so that the cost of cytarabine remains high, so it is urgent to develop a method with few reaction steps, few chemical reagents involved, low price, and high yield. , a new process for the green production of cytarabine with strong operability

Method used

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  • Technology for producing cytarabine through chemical synthesis method
  • Technology for producing cytarabine through chemical synthesis method
  • Technology for producing cytarabine through chemical synthesis method

Examples

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Effect test

Embodiment 1

[0046] Add 80g (0.299mol) araburidine and 300mL hexamethyldisilazane HMDS into a 1L reactor, seal and pressurize (8Kg), heat slowly to 130°C, keep the temperature for 40h, then slowly cool down to about 60°C, Pour into a 1000mL three-neck flask, stir, concentrate under reduced pressure, recover excess hexamethyldisilazane HMDS, add a small amount of ethanol, concentrate to dryness, then add 500mL of methanol, cool down to about 10°C, and stir rapidly for 1 hour. Concentrate to dryness to obtain crude product. The crude product was recrystallized with acetone, filtered and dried to obtain 51 g of the product with a yield of 70.6%.

Embodiment 2

[0048] Add 80g (0.299mol) araburidine and 400mL hexamethyldisilazane HMDS into a 1L reactor, seal and pressurize (10Kg), heat slowly to 150°C, keep the temperature for 60h, then slowly cool down to about 80°C, Pour into a 1000mL three-necked flask, stir, concentrate under reduced pressure, recover excess hexamethyldisilazane HMDS, add a small amount of acetone, concentrate to dryness, then add 500mL methanol, cool down to about 20°C, and stir rapidly for 1 hour. Concentrate to dryness to obtain crude product. The crude product was recrystallized with ethanol, filtered, and dried to obtain 58 g of the product, with a yield of 80.5%.

Embodiment 3

[0050] Add 80g (0.299mol) araburidine and 500mL hexamethyldisilazane HMDS into a 1L reactor, seal and pressurize (10Kg), heat slowly to 150°C, keep the temperature for 72h, then slowly cool down to about 80°C, Pour into a 1000mL three-necked flask, stir, concentrate under reduced pressure, recover excess hexamethyldisilazane HMDS, add a small amount of methanol, concentrate to dryness, repeat three times, then add 500mL of methanol, cool down to about 20°C, and stir rapidly After 1 hour, concentrate to dryness to obtain crude product. The crude product was recrystallized with ethanol, filtered and dried to obtain 65 g of the product with a yield of 90%.

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Abstract

The invention discloses a technology for producing cytarabine through a chemical synthesis method, relating to a synthesis technology of an organic compound and aiming to provide a technology for producing the cytarabine through the chemical synthesis method, which has the advantages of cheap and available raw material, simple reaction condition, low cost, environmental protection and high yield. Based on the solving technical scheme, the technology for producing the cytarabine through the chemical synthesis method has a synthetic route which comprises the following synthesis steps of: firstly, reacting the cytarabine (1) used as a starting raw material with hexamethyldisilazane (HMDS) for 10-80h under the pressure of 5-20kg and at the temperature of 70-160 DEG C, cooling, stirring and vacuum concentrating a reaction system, and removing and recovering redundant hexamethyldisilazane to obtain an intermediate (II), wherein the dosage of the hexamethyldisilazane is 2-10 times larger than the weight of the cytarabine; secondly, dissolving the intermediate (II) into a proper solvent, and cooling or stirring to prepare crude cytarabine. The invention is used for preparing an anticancer drug.

Description

Technical field: [0001] The invention relates to a synthesis process of organic compounds, in particular to a process for producing cytarabine by chemical synthesis. Background technique: [0002] Cytarabine Molecular Structural Formula: [0003] [0004] Cytarabine (Cytarabine), also known as 1-β-D-arabinosylcytosine (1-β-D-Arabinofuranosylcytosine, abbreviated as Ara-C), mainly acts on the pyrimidine antimetabolite drug in the cell S proliferation phase , Interfering with cell proliferation by inhibiting cellular DNA synthesis. After entering the human body, cytarabine is phosphorylated by kinases and converted into cytarabine triphosphate and cytarabine diphosphate. The former can strongly inhibit the synthesis of DNA polymerase, and the latter can inhibit the conversion of cytarabine diphosphate into Deoxycytidine diphosphate, thereby inhibiting cellular DNA polymerization and synthesis. Cytarabine can also inhibit the synthesis of membrane glycolipids and membrane...

Claims

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Application Information

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IPC IPC(8): C07H19/09C07H1/00
Inventor 渠桂荣郭海明杨西宁张新迎王东超牛红英夏然李涛王菲菲张倩增超
Owner HENAN NORMAL UNIV
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