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Preparation method of etoposide, teniposide and analogs of etoposide and teniposide

A technology of teniposide and etoposide, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of difficult configuration control, high toxicity, low yield, etc., and achieves the scope of application Wide, easy-to-operate effects

Inactive Publication Date: 2016-05-11
JIANGXI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods all have the disadvantages of low yield, difficult configuration control, and high toxicity.

Method used

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  • Preparation method of etoposide, teniposide and analogs of etoposide and teniposide
  • Preparation method of etoposide, teniposide and analogs of etoposide and teniposide
  • Preparation method of etoposide, teniposide and analogs of etoposide and teniposide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of podophyllotoxin 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucose)podophyllotoxin glycoside

[0029]

[0030] Step 1: Synthesis of a perbenzoyl-protected glucose donor:

[0031]

[0032] Under the protection of nitrogen, 5g, 8.4mmol of fully Bz-protected glucose with exposed anomeric position and 1.87g, 10.1mmol of o-alkynylbenzoic acid were dissolved in dry 10mL DCM, and then 2g, 10.1mmol of EDCI, and 1g, 10mmol of DMAP were added to the system And DIPEA3ml, 16.7mmol, and stirred at room temperature for 3h, TLC tracking to the end of the reaction. The crude product was concentrated under reduced pressure in the reaction system, and then the glucosynyl ester donor (6.1 g, 95%) was obtained by column chromatography;

[0033] Step 2: Preparation of podophyllotoxin 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucose)podophyllotoxin glycoside

[0034]

[0035] Under nitrogen protection, 115mg, 0.15mmol of whole benzoyl-protected glucose donor and 41mg, 0.1mmol of podo...

Embodiment 2

[0038] Preparation of epipodophyllotoxin 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucose) epipodophyllotoxin glycoside

[0039]

[0040] Step 1: as shown in embodiment 1 step 1;

[0041] Step 2: Preparation of epipodophyllotoxin

[0042]

[0043] Under nitrogen protection, dissolve 1.0g, 2.41mmol of podophyllotoxin and 993.2mg, 9.65mmol of sodium bromide in 24mL of acetonitrile, then add 0.63mL of methanesulfonic acid, 9.65mmol of Water, then add barium carbonate 1.906g, 9.65mmol, stir at room temperature until the reaction is complete. The reaction system was extracted and dried, concentrated under reduced pressure to obtain a crude product, and purified by column chromatography to obtain 950 mg of the target product, 95%;

[0044] Step 3: Preparation of epipodophyllotoxin 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucose) epipodophyllotoxin glycoside

[0045]

[0046] Under nitrogen protection, dissolve 230mg, 0.3mmol of whole benzoyl-protected glucose donor and 41mg, 0.1mmol of...

Embodiment 3

[0048] Preparation of podophyllotoxin 4-O-(2,3,6-tri-O-benzoyl-β-L-rhamnose)podophyllotoxin glycoside

[0049]

[0050] Step 1: Preparation of all-benzoyl-protected rhamnose donor;

[0051]

[0052] Under the protection of nitrogen, 5g, 10.5mmol of rhamnose and 2.3g, 12.6mmol of fully Bz-protected rhamnose exposed at the anomeric position and 2.3g, 12.6mmol of o-alkynylbenzoic acid were dissolved in dry 12mL DCM, and then 2.3g, 11.6mmol of EDCI was added to the system , DMAP1.2g, 11.6mmol and DIPEA3.5ml, 19.5mmol, and stirred at room temperature for 3h, followed by TLC until the end of the reaction. The reaction system was concentrated under reduced pressure to obtain the crude product, and then column chromatography yielded 6.1 g of the rhamnosynyl ester donor, 93%;

[0053] Step 2: Preparation of podophyllotoxin 4-O-(2,3,6-tri-O-benzoyl-β-L-rhamnose)podophyllotoxin glycoside

[0054]

[0055] Under the protection of nitrogen, dissolve 97mg, 0.15mmol of rhamnose do...

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Abstract

The invention discloses a preparation method of etoposide, teniposide and analogs of etoposide and teniposide. The preparation method includes the following steps of 1, selective protection of 4'domethylpodophyllotoxin4'hydroxy; 2, introduction of 4 hydroxy hydroxyl; 3, removal of a protecting group. The method is mild in reaction condition and environmentally friendly, and the yield and purity of the products are high.

Description

technical field [0001] The invention relates to a preparation method of etoposide, teniposide and analogues thereof. Background technique [0002] Lignin compounds widely exist in the plant kingdom and originate from the oxidative dimerization of phenylpropanoid as secondary metabolites. [1] So far, lignin compounds have been isolated from the roots, stems, leaves, seeds and fruits of seventeen families of plants. Although from the perspective of chemical structure, the molecular structure of this type of compound only contains two C 6 -C 3 Phenylpropanoid units, but this type of compound exhibits structural complexity and diversity by changing the connection mode of two phenylpropanoid units. [0003] Biological activity tests show that lignan compounds have very good medicinal activities, mainly including anti-tumor, anti-infection, immunosuppression, cardiovascular and cerebrovascular protection, anti-oxidation and anti-virus. The most famous lignin compound is podoph...

Claims

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Application Information

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IPC IPC(8): C07H17/04C07H1/00
CPCY02P20/55C07H17/04C07H1/00
Inventor 孙建松刘慧廖进喜涂媛鸿熊斌
Owner JIANGXI NORMAL UNIVERSITY
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