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One-step method for synthesizing tryptamine ketone and derivative

A synthesis method and a derivative technology are applied in the synthesis field of tryptamine and its derivatives, which can solve the problems of difficulty in large-scale production, unpleasant smell and the like, and achieve the effect of high reaction yield

Inactive Publication Date: 2008-05-14
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] Looking at the synthesis methods of tryptanthrin and its derivatives in the past century, indoloquinone and indolinone are mainly used as starting materials, and the mainstream method should be the reaction of indolequinone and isatoic anhydride. This method is relatively simple and the yield High, the reaction conditions are also mild, but with pyridine as the solvent, the smell is unpleasant, and it is difficult to produce on a large scale

Method used

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  • One-step method for synthesizing tryptamine ketone and derivative
  • One-step method for synthesizing tryptamine ketone and derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of tryptanthrin

[0029] Dissolve equimolar indoloquinone and isatoic anhydride in 1,2-dichloroethane, add tributylamine, heat to reflux for 2 hours, evaporate the solvent and catalyst after cooling. The target compound tryptanthrin was obtained after recrystallization from ethanol with a yield of 92%.

Embodiment 2

[0030] Embodiment 2: the synthesis of 8-chlorotryptanthrin

[0031] Dissolve equimolar 5-chloroindoloquinone and isatoic anhydride in carbon tetrachloride, add N,N-dipropylbutylamine, heat and reflux for 3 hours, and evaporate the solvent and catalyst after cooling. The target compound 8-chlorotryptanthin was obtained after recrystallization from ethanol with a yield of 90%.

Embodiment 3

[0032] Example 3: Synthesis of 2-ethoxyl-8-methoxytryptanthrin

[0033] Dissolve equimolar 5-methoxyindolequinone and 6-ethoxyisatoic anhydride in n-propanol, add sodium n-propoxide, heat and reflux for 2.5 hours, add dilute hydrochloric acid to neutralize after cooling, evaporate solvent. The target compound 2-ethoxy-8-methoxytryptanthrin was obtained after recrystallization from ethanol with a yield of 75%.

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Abstract

The invention relates to a method for producing tryptamine ketones and the derivatives shown in formula (I), wherein the compounds are obtained through reaction between indole quinines or the derivatives and isatoic anhydrides or the derivatives. The invention is characterized in that the solvent is selected from lower alcohols, chloroform, carbon tetrachloride, 1, 2-dichloroethane, tetrahydrofuran, dioxane, toluene, xylene, DMF and DMSO of C2-C5; the catalyst is inorganic base or organic base; R1, and R2 is selected from hydrogen, hydroxyl and alkoxy, amino of C1-C6, halogen, alkyla, amide, substituted aminomethyl C1-C8 or amide methyl.

Description

technical field [0001] The invention relates to a synthesis method of tryptanthrin and its derivatives. Background technique [0002] Tryptanthrin is an active ingredient in the traditional Chinese medicine Folium Folium and Indigo Daisy, and is used as an anticancer agent. It has a cytocidal effect on leukemia cells and has a preventive effect on intestinal cancer. As an antifungal agent, tryptanthrin is more effective against dermatological fungi such as Microsporum lanoides, Trichophyton trichophyton, Microsporum gypsum, Violet phyton, Trichophyton gypsum, Trichophyton rubrum, Epidermophyton flocculus, etc. Strong antibacterial effect, the minimum inhibitory concentration is 5μg / ml. The anti-inflammatory effect of tryptanthrin can inhibit NO synthesis, and the purpose of inhibiting NO synthesis is achieved by inhibiting the gene expression of inducible NO synthase. The mechanism of tryptanthrin inhibiting the production of prostaglandins is different from that of inhibi...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 刘建利王翠玲刘竹兰
Owner NORTHWEST UNIV
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