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Preparation method and application of dehydrobufotenine

A technology of dehydrobufatryptamine and tetrahydropyrrole, applied in the field of preparation of dehydrobufatryptamine, which can solve the problems of environmental pollution, high production cost, low yield, etc.

Active Publication Date: 2021-07-06
HEBEI UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method overcomes the defects of low yield, high production cost and environmental pollution in the preparation of dehydrobufatryptamine in the prior art

Method used

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  • Preparation method and application of dehydrobufotenine
  • Preparation method and application of dehydrobufotenine
  • Preparation method and application of dehydrobufotenine

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preparation example Construction

[0052] The reaction formula of preparation method of the present invention is:

[0053]

[0054]The compound 29 is 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetic acid methyl ester; the compound 30 is 2-(5-methoxy-4-nitro -1H-indol-3-yl)-2-oxoacetic acid methyl ester; The compound 31 is 2-(5-methoxy-4-nitro-indoline-3-yl) methyl acetate, The compound 32 is 6-methoxy-1,2,2a,5-tetrahydropyrrole[4,3,2-de]quinolin-4(3H)-one, and the compound 33 is 6-methoxy Base-1,2,2a,3,4,5-hexahydropyrrole[4,3,2-de]quinoline, the compound 34 is 6-methoxy-2a,3,4,5-tetrahydro Pyrrole [4,3,2-de] quinoline-1 (2H) tert-butyl carboxylate), the compound 35 is 6-methoxy-4,5-dihydropyrrole [4,3,2-de] Quinoline-1 (3H) tert-butyl formate), said compound dehydrobufatryptamine is iodide 6-methoxy-5,5-dimethyl-1,3,4,5-tetrahydropyrrole [ 4,3,2-de]quinoline.

[0055] The first step, using 5-methoxyindole as a raw material to obtain compound 2-(5-methoxyl-1H-indol-3-yl)-2-oxoacetic acid methyl ester through acyl...

Embodiment 1

[0057] The concrete steps of its preparation method are as follows:

[0058] In the first step, add 5-methoxyindole (1.00g, 6.80mmol) and diethyl ether (14mL) into a 100mL round-bottomed flask, add oxalyl chloride (0.68mL) dropwise at 0°C, react for 1.5h and then filter with suction , the solid obtained by suction filtration was added to a 100mL round-bottomed flask, and MeOH (60mL) was added at 0°C, and after reaction for 1h, suction filtration was obtained to obtain compound 29, a yellow solid, with a yield of 98%; The relevant parameters are: 1 H NMR (400MHz, DMSO-d 6 )δ12.32(s,1H),8.37(d,J=3.4Hz,1H),7.66(s,1H),7.45(d,J=8.8Hz,1H),6.92(dd,J=8.8,2.6 Hz,1H),3.89(s,3H),3.80(s,3H); 13 C NMR (100MHz, DMSO-d 6 )δ179.05(s),164.55(s),156.65(s),138.72(s),131.90(s),126.91(s),114.00(s),113.92(s),112.77(s),103.53( s), 55.79(s), 52.95(s), confirm that compound 29 is methyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate;

[0059] In the second step, compound 29 (1.50g, 6.44mmol) was added...

Embodiment 2

[0067] The assay of the anti-tobacco mosaic virus activity of above-mentioned dehydrobufatryptamine, assay procedure is as follows:

[0068] The first step, tobacco mosaic virus purification and concentration determination:

[0069] Tobacco mosaic virus purification and concentration determination were carried out in accordance with the Tobacco Mosaic Virus SOP specification compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the virus crude extract was centrifuged twice with polyethylene glycol, the measured concentration was 20 μg / mL, and refrigerated at 4 °C spare;

[0070] In the second step, the preparation of the above-mentioned dehydrobufatryptamine pharmaceutical solution:

[0071] Weigh 40 mg of dehydrobufatryptamine as the original drug, and then add 0.4 mL of DMF to each of the original drugs for dissolution to obtain 1 × 10 5 μg / mL mother liquor, and then diluted with Tween 80 aqueous solution with a mass percentage concentr...

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Abstract

The invention relates to a preparation method and application of dehydrobufotenine. According to the preparation method, 5-methoxyindole which is cheap and easy to obtain is used as a raw material, and an ester functional group is introduced to the 3-site of an indole skeleton through a Friedel-Crafts acylation reaction to obtain an important intermediate, namely 2-(5-methoxy-1H-indole-3-yl)-2-methyl oxoacetate, so that simple, convenient and mild conditions are provided for subsequent construction of a quinoline structure. The method overcomes the defects of low yield, high production cost and environmental pollution in preparation of dehydrobufotenine in the prior art. The invention also discovers that dehydrobufotenine has good activity of resisting plant viruses and germs.

Description

technical field [0001] The technical solution of the present invention relates to a biocide containing pyrrolo[4,3,2-de]quinoline skeleton dehydrobufotenine (dehyrobufotenine), specifically the preparation method and application of dehyrobufotenine. Background technique [0002] Dehydrobufatryptamine is a natural alkaloid containing a pyrrolo[4,3,2-de]quinoline skeleton, and its chemical structural formula is as follows: [0003] [0004] Toad serum and toad venom contain pharmacologically active indole alkaloid components, such as serotonin, bufotryptamine, bufotenine, bufotenidine, bufothionine, dehydro Bufa tryptamine (dehydrobufotenine), tryptamine (tryptamine), etc., these indole alkaloids have a wide range of physiological activities, such as anti-tumor, anti-inflammatory, bactericidal, etc. (Sanders-Bush, E.; Mayer, S.E.In Goodman and Gilman's The pharmacological basis of therapeutics, 10 th ed.; Hardman, J.G.; Limbird, L.E., Eds.; McGraw-Hill: NewYork, NY, 2001...

Claims

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Application Information

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IPC IPC(8): C07D471/06A01N43/90A01P1/00A01P3/00
CPCC07D471/06A01N43/90
Inventor 卢爱党田兆永王兹稳王铁男李红岩师利
Owner HEBEI UNIV OF TECH
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