Preparation method of tryptanthrin compound

The technology of a compound, tryptanthrin, is applied in the field of preparation of tryptanthrin compounds, which can solve the problems of harsh conditions, heavy pollution and high cost, and achieve the effect of mild conditions, simple raw materials and low toxicity

Active Publication Date: 2017-09-08
HUAZHONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the defects of the existing preparation methods of tryptanthrin and its derivatives, such as high cost, heavy pollution, harsh conditions, difficult post-treatment, etc., and provide a low-cost, environmentally friendly, mild condition And the preparation method of tryptanthrin compound with simple post-treatment method

Method used

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  • Preparation method of tryptanthrin compound
  • Preparation method of tryptanthrin compound
  • Preparation method of tryptanthrin compound

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preparation example Construction

[0013] The present invention provides a preparation method of tryptanthrin compound, said tryptanthrin compound is a compound of the structure shown in formula (2), the method comprising: in the presence of peroxide and basic compound, in In an organic solvent, the compound of the structure shown in the formula (1) is subjected to an oxidative cyclization reaction to obtain a compound of the structure shown in the formula (2); the peroxide is selected from tert-butyl hydroperoxide and / or hydrogen peroxide ;

[0014]

[0015] Among them, R 1 -R 4 Each is independently selected from H, C1-C10 alkyl, C1-C10 alkoxy and halogen.

[0016] According to the present invention, the method can carry out the oxidative cyclization of the compound of the structure shown in the above formula (1) in the presence of tert-butyl hydroperoxide and a basic compound, thereby preparing the compound of the structure shown in the formula (2) .

[0017] Among them, specific examples of C1-C10 al...

Embodiment 1

[0051] This example is used to illustrate the preparation method of tryptanthrin compounds of the present invention.

[0052]

[0053] The compound of the structure shown in 1mmol formula (1-1), 65% by weight of TBHP aqueous solution (consumption makes the amount of TBHP be 1mmol) and 1mmol of K 3 PO 4 Added into 4mL of acetonitrile, reacted at 25°C and a stirring speed of 600rpm for 12h, extracted with dichloromethane, concentrated and used silica gel column chromatography (dichloromethane / petroleum ether mixture with a volume ratio of 3:2 was used as eluate) was separated and purified to obtain the compound of formula (2-1) (0.45 mmol, yield 90%).

[0054] 1 H NMR (600MHz, CDCl 3 ): δ=8.61(d, J=7.8Hz, 1H), 8.42(d, J=7.8Hz, 1H), 8.02(d, J=7.8Hz, 1H), 7.91(d, J=6.6Hz, 1H ),7.85(d,J=7.2Hz,1H),7.78(d,J=7.2Hz,1H),7.67(d,J=7.2Hz,1H)7.43(d,J=7.2Hz,1H).

[0055] 13 C NMR (150MHz, CDCl 3 ): δ=182.5, 158.0, 146.5, 146.3, 144.3, 138.2, 135.1, 130.7, 130.2, 127.5, 127.2, 125.4...

Embodiment 2

[0057] This example is used to illustrate the preparation method of tryptanthrin compounds of the present invention.

[0058]

[0059] According to the method described in Example 1, the difference is that the compound of the structure shown in the formula (1-2) is used to replace the compound of the structure shown in the formula (1-1), and K 2 CO 3 instead of K 3 PO 4 , thereby obtaining the compound (0.43 mmol, yield 86%) represented by formula (2-2).

[0060] 1 H NMR (400MHz, CDCl 3 ): δ=8.35(d, J=8.0Hz, 1H), 8.09(s, 1H), 7.82(d, J=8.4Hz, 1H), 7.61(s, 1H), 7.58(d, J=8.4Hz ,1H),7.48(d,J=8.0Hz,1H),2.51(s,3H),2.41(s,3H).

[0061] 13 C NMR (100MHz, CDCl 3 ): δ=182.2, 157.4, 144.1, 143.8, 143.6, 140.8, 138.4, 137.0, 136.0, 130.2, 126.9, 125.1, 123.2, 121.8, 117.4, 21.7, 21.2.

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Abstract

The invention relates to the field of synthesis of tryptanthrin and discloses a preparation method of a tryptanthrin compound. The tryptanthrin compound is a compound having a structure shown in formula (2); the preparation method comprises a step of performing oxidative cyclization reaction on a compound having a structure shown in formula (1) in an organic solvent in the presence of a peroxide and an alkaline compound to obtain the compound having the structure shown in formula (2); the peroxide is selected from tert-butyl hydroperoxide and/or hydrogen peroxide. Raw materials used in the preparation method provided by the invention are simple, low in toxicity, green and environment-friendly; the preparation method realizes reaction at room temperature basically, are mild in condition, and can be used for implementing industrial production of the tryptanthrin compound.

Description

[0001] This application claims the priority of the previous Chinese invention patent application with the filing date of March 1, 2016, the application number of 201610114468.2, and the title of the invention "a preparation method of tryptanthrin compounds". technical field [0002] The present invention relates to the synthesis field of tryptanthrin, in particular to a preparation method of tryptanthrin compounds. Background technique [0003] Tryptanthrin is one of the main components of the traditional Chinese medicine Qingdai and Daqingye and its medicinal plants Strobilanthes cusia, Polygonum tinctorum Lour and Isatistinctoria. Modern pharmacological studies have shown that tryptanthrin and its derivatives have good anticancer, anti-inflammatory, antibacterial and parasitic killing activities. [0004] At present, the relatively simple method for synthesizing tryptanthrin and its derivatives is the Bergman method. The method uses N-methylpiperidine as a catalyst, N'N-d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 贾丰成徐程周志文吴安心
Owner HUAZHONG NORMAL UNIV
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