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A kind of synthetic method of semigossypol, gossypol and their analogs

A synthetic method, the technology of semi-gossypol, which is applied in the field of gossypol and their analogs, and the synthesis of semi-gossypol, can solve the problem of single product structure, difficult synthesis of semi-gossypol and gossypol analogs, and inability to obtain semi-gossypol and gossypol Gossypol analogs and other issues

Active Publication Date: 2021-11-30
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although the current extraction methods from natural products are relatively mature, only gossypol products can be obtained, and semi-gossypol is difficult to obtain, and semi-gossypol and analogs of gossypol cannot be obtained
The chemical synthesis method has a longer synthetic route, and it is also difficult to realize the synthesis of semi-gossypol and gossypol analogues, and the synthesized product structure is relatively single

Method used

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  • A kind of synthetic method of semigossypol, gossypol and their analogs
  • A kind of synthetic method of semigossypol, gossypol and their analogs
  • A kind of synthetic method of semigossypol, gossypol and their analogs

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] The synthesis of gossypol (compound X VI-1), synthetic route is as follows:

[0143]

[0144] Concrete synthetic steps are as follows:

[0145] (1) Add 6.8g of compound I-1 isopropyl maltol, 3 equivalents of potassium carbonate and 1.2 equivalents of propargyl bromide to 150 ml of acetonitrile, heat at 80°C for 14 hours, cool to room temperature, filter, After the solvent was evaporated under reduced pressure, 8.0 g of compound II-1 was obtained by column chromatography with a yield of 94%. 1 H NMR (400MHz, CDCl 3 )δ7.71(d, J=5.6Hz, 1H), 6.35(d, J=5.6Hz, 1H), 4.91(d, J=2.4Hz, 2H), 3.54(hept, J=7.0Hz, 1H) , 2.46(t, J=2.4Hz, 1H), 1.23(d, J=7.0Hz, 6H). 13 C NMR (101MHz, CDCl 3 )δ175.19, 167.55, 153.96, 141.01, 116.92, 79.21, 75.76, 58.72, 27.21, 19.92.HR-MS(ESI)calcd.for[C 11 h 12 o 3 +Na] + 215.0679, found: 215.0678.

[0146] (2) 8.0 g of compound II-1, 3 equivalents of potassium carbonate, 1.5 equivalents of allyl bromide, 0.1 equivalents of cuprous iodide an...

Embodiment 2

[0164] The synthesis of methyl-gossypol (compound XVI-2), the synthetic route is as follows:

[0165]

[0166] Concrete synthetic steps are as follows:

[0167] (1) Add 15g of compound I-2 methyl maltol, 3 equivalents of potassium carbonate and 1.2 equivalents of propargyl bromide to 300 ml of acetonitrile, heat at 80°C for 12 hours, cool down to room temperature, and use a short silica gel column After filtering and distilling off the solvent under reduced pressure, 17.2 g of compound II-2 was obtained by column chromatography with a yield of 88%. 1 H NMR (400MHz, CDCl3) δ7.63(d, J=5.6Hz, 1H), 6.39-6.30(m, 1H), 4.88(d, J=2.4Hz, 2H), 2.44(t, J=2.4Hz , 1H), 2.38(s, 3H). 13 C NMR (101MHz, CDCl3) δ174.84, 160.82, 153.77, 143.02, 117.29, 79.19, 75.75, 58.85, 15.42. HR-MS (ESI) calcd.for[C 9 h 8 o 3 +Na] + 187.0366, found 187.0367.

[0168] (2) 17.2 g of compound II-2, 3 equivalents of potassium carbonate, 1.5 equivalents of allyl bromide, 0.1 equivalents of cuprous iodid...

Embodiment 3

[0186] In Example 1, in step (1), 1.0 equivalent of potassium carbonate was added, 1.0 equivalent of propargyl bromide was added, and the reaction was carried out at 40° C., and the rest of the reaction conditions were unchanged. The yield of compound II-1 was 80%.

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Abstract

The invention discloses a method for synthesizing hemigossypol, gossypol and their analogues. The method uses substituent-containing maltol as a raw material to synthesize hemigossypol, gossypol and their analogs through multistage reactions including coupling, rearrangement, reduction, oxidation and cyclization. The method changes the current situation of extracting gossypol from the roots, stems, leaves and seeds of the natural mallow plant cotton, and creates a new route for artificially synthesizing semi-gossypol, gossypol and their analogs.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing hemigossypol, gossypol and their analogs. Background technique [0002] Gossypol, also known as gossypol or gossypol, is a polyphenolic compound widely present in the seeds, leaves, stems and roots of cotton, a plant of the Malvaceae family. Its content in cottonseed, cotton root and cotton husk is 0.15%-1.8% and 0.56%-3% respectively. Gossypol can be divided into free gossypol and bound gossypol according to its existing form, and the sum of the two is called total gossypol. It is generally believed that bound gossypol cannot be absorbed by the digestive tract, and free gossypol can be absorbed by the digestive tract, so gossypol is usually referred to as free gossypol. In the 1960s, scientists from the former Soviet Union discovered that gossypol can inhibit animal tumor cells. Modern medical research has proved that gossypol not only has anti-tumor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/72C07C47/57C07C47/575C07C43/205C07C43/23
CPCC07C41/01C07C41/16C07C41/18C07C41/26C07C41/30C07C43/2055C07C43/23C07C45/29C07C45/36C07C45/64C07C45/72C07C47/57C07C47/575C07D309/40C07C49/255C07C43/202Y02P20/55
Inventor 祝诗发曹同祥王永东黄志鹏
Owner SOUTH CHINA UNIV OF TECH
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