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Novel production process for chemical synthesis of zeylenone

A synthetic process and chemical technology, applied in the field of synthetic sansaporenone, can solve the problems of inability, small content, low yield, etc.

Inactive Publication Date: 2012-09-19
苏州世林医药技术发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the content of this compound in natural products is small, and the extraction and separation are difficult, so it cannot be adapted for in-depth druggability evaluation research
The chemical total synthesis of this compound has been reported (Chemical & Pharmaceutical Bulletin (2006), 54 (10), 1459-1461.), but due to the low yield and poor reproducibility, it cannot be the kilogram required for animal experiments and clinical experiments. magnitude

Method used

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  • Novel production process for chemical synthesis of zeylenone
  • Novel production process for chemical synthesis of zeylenone
  • Novel production process for chemical synthesis of zeylenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1 prepares intermediate III:

[0016] Put 50 grams of compound II, 150 grams of n-bromosuccinimide (NBS), and 250 mL of benzene into a 500 mL three-necked round-bottomed flask, and stir at 25°C for 5 hours. The insoluble matter was filtered off, and the solution was extracted three times with water (100 mL×3). The organic phase was dried with anhydrous sodium sulfate, and recrystallized with ethanol to obtain 55 g of light yellow solid compound III. 1 H NMR (400mHz, CDCl 3 ) ppm: 7.98 (m, ArH, 4H), 7.48-7.35 (m, ArH, 6H), 5.61 (m, CH=CH, 2H), 5.01 (m, 1H), 4.82 (s, 1H), 4.60- 4.30 (m, 3H).

Embodiment 2

[0017] Embodiment 2 prepares intermediate IV:

[0018] 50 g of compound III, 150 mL of 1N aqueous sodium hydroxide solution, and 100 mL of methanol were put into a 500 mL three-necked round-bottomed flask and stirred at 55° C. for 10 hours. The reaction mixture was adjusted to pH=4 with 10% citric acid, the precipitated matter was filtered, and the filter cake was washed with water three times (50 mL×3). Air-dried and recrystallized from ethanol to obtain 45 g of compound IV as a white solid. 1 H NMR (400mHz, CDCl 3 ) ppm: 7.97 (m, ArH, 4H), 7.45-7.33 (m, ArH, 6H), 5.59 (m, CH=CH, 2H), 5.00 (m, 1H), 4.81 (s, 1H), 4.58- 4.25 (m, 3H).

Embodiment 3

[0019] Embodiment 3 prepares intermediate V:

[0020] Add 40 g of Compound IV and 150 mL of chloroform into a 500 mL three-neck round bottom flask, and stir at 50°C. Add 9 grams of manganese dioxide every hour for a total of 7 times. After reacting for 10 hours, the insoluble substances were filtered off, the solution was concentrated, separated on a silica gel column, and rinsed with ethyl acetate and petroleum ether to obtain 25 g of white solid compound V. 1 HNMR (400mHz, CDCl 3 ) ppm: 7.97 (m, ArH, 4H), 7.47-7.37 (m, ArH, 6H), 6.75 (m, CH=CH, 1H), 6.35 (m, CH=CH, 1H), 5.22 (m, 1H ), 5.01(s, 1H), 4.68(m, 1H), 4.45(m, 1H).

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Abstract

The invention discloses a novel production process for chemical synthesis of zeylenone. The chemical name of the zeylenone is (4R, 5S, 6S)-4-(benzoyloxy)-6-[(benzoyloxy) methyl]-5, 6-dihydroxy-2-cyclohexen-1-one. The CAS number of the zeylenone is 193410-84-3. According to the novel production process for the chemical synthesis of the zeylenone, production cost can be reduced, yield of pharmaceutical chemicals of the zeylenone can be improved, and an effective preparation method of the novel chemical medicine can be provided.

Description

technical field [0001] The invention belongs to the field of pharmaceutical synthesis chemistry, and in particular relates to a method for synthesizing sanspotenone at the kilogram level starting from simple raw materials (3R, 4S, 5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid . Background technique [0002] Over the years, people's research has shown that polyoxo-substituted cyclohexene is a kind of natural components with unique structure. So far, there have been more than 20 species of plants from the genus Ziyupan in the family Annonaceae, the genus Piper in the family Piper and the genus Croton in the family Euphorbiaceae. obtained in isolation. At the end of the 1960s, Kupchan et al. reported that the crotepoxide obtained from long-eared croton showed strong anti-tumor activity in animals, which once aroused people's strong interest in this type of ingredients (Thebtaranonth C, Thebtaranonth Y.Naturally occurring cyclohexene oxides. Accounts Chem Res, 1986, 1984)....

Claims

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Application Information

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IPC IPC(8): C07C69/78C07C67/46
Inventor 余强朱永明许琼明张福治张仁延杨世林
Owner 苏州世林医药技术发展有限公司
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