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Preparation method of natural product veranamine alkaloid

A technology of natural products and alkaloids, applied in the direction of organic chemistry, can solve problems such as low yield and harsh reaction conditions, and achieve the effects of reducing costs, improving safety, and simplifying experimental operations

Pending Publication Date: 2022-07-29
HEBEI UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The purpose of the present invention is to provide a method for synthesizing the natural product alkaloid veranamine with 3-bromoaniline (1) as raw material for the disadvantages of low yield caused by harsh raw materials and reaction conditions in the prior art

Method used

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  • Preparation method of natural product veranamine alkaloid
  • Preparation method of natural product veranamine alkaloid
  • Preparation method of natural product veranamine alkaloid

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preparation example Construction

[0052] (5) Preparation of Veranamine: Ethyl 2-acetamido-1-(7-bromo-2,2-dimethyl-1,2-dihydroquinolin-4-yl)acetate Phosphorus-catalyzed ring closure to produce the alkaloid veranamine.

[0053] Reaction 3 is as follows:

[0054]

Embodiment 1

[0055] Example 1: Preparation of Veranamine

[0056] (1) Preparation of 7-bromo-2,2,4-trimethyl-1,2-dihydroquinoline (2)

[0057] Its reaction formula is:

[0058]

[0059] 3-Bromoaniline (20.014g, 116.34mmol) and iodine (5.906g, 23.27mmol) were dissolved in acetone (300mL), heated to reflux (65°C) and stirred for 120h. During the reaction period, acetone was regularly added, and TLC detected that the reaction was complete After that, the solution was desolvated in vacuo, and a pale yellow oily liquid was obtained by column chromatography. The yield was 75%. 1 H NMR (400MHz, CDCl 3 )δ6.88(d,J=8.1Hz,1H,Ar-H),6.73(dd,J=8.1and 1.7Hz,1H,Ar-H),6.58(d,J=1.8Hz,1H,Ar- H), 5.33–5.29 (m, 1H, CH), 3.82 (s, 1H, NH), 1.96 (d, J=1.4Hz, 3H, C=CCH) 3 ),1.27(s,6H,2CH 3 ); 13 C NMR (101MHz, CDCl 3 ) δ143.5, 128.7, 128.0, 125.0, 121.8, 121.0, 120.7, 116.1, 52.5, 30.7, 18.5, confirming that the product is 7-bromo-2,2,4-trimethyl-1,2-dihydroquinoline.

[0060] (2) Preparation of 7-brom...

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Abstract

The invention relates to a preparation method of a natural product veranamine alkaloid. According to the method, 7-bromine-2, 2-dimethyl-1, 2-dihydroquinoline-4-formaldehyde (3) and nitromethane are subjected to an addition reaction to generate 1-(7-bromine-2, 2-dimethyl-1, 2-dihydroquinoline-4-yl)-2-nitroethane-1-alcohol (4), so that trimethylsilyl cyanide with extremely high toxicity is prevented from being used as a raw material; according to the method, 2-acetamido-1-(7-bromo-2, 2-dimethyl-1, 2-dihydroquinoline-4-yl) ethyl acetate (5) is subjected to cyclization under the action of phosphorus oxychloride, and compared with the use of phosphorus pentoxide with strong corrosivity and microwave heating, the reaction conditions are simple and safe. The total yield of the reaction is increased from 25% to 28.3%, the experimental operation is simplified, the reaction conditions are optimized, and the feasibility of the route is greatly improved.

Description

technical field [0001] The invention relates to a preparation method of natural product veranamine alkaloid, and belongs to the technical field of resources and medicine and chemical industry. Background technique [0002] The natural product veranamine is a marine alkaloid with a benzo[c][2,7]naphthyridine skeleton. In 2009, veranamine was first isolated from the marine sponge Verongula rigida of the Florida Keys by Harman et al. The study found that veranamine has good antidepressant and anxiolytic activities and has high research value (WO2009 / 049030). [0003] At present, veranamine alkaloids are mainly obtained by separation and extraction from marine sponges. Due to the low content of the active ingredient in natural substances and the high development cost, research on its biological activity is limited. Therefore, it is very important to explore a new route to synthesize veranamine with easily available raw materials, high yield, mild conditions and simple experimen...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 卢爱党马钰聪薛伟苑文英殷向阳
Owner HEBEI UNIV OF TECH
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