Green synthetic method of beta-carboline compound

A green synthesis and compound technology, applied in the direction of organic chemistry, can solve the problems of potential safety hazards, low yield, and large environmental hazards, and achieve the effects of high yield, simple preparation, safe and environmentally friendly preparation

Inactive Publication Date: 2014-06-18
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there are many methods for obtaining β-carboline rings through oxidative decarboxylation and dehydrogenation reactions, and the main methods are summarized as follows: 1) Using SeO 2 In the presence of acetic acid as an oxidizing agent, β-carboline compounds can be obtained by reflux reaction (J. Med. Chem, 1987, 30(4): 750-753); 2) Potassium dichromate is used as an oxidizing agent, β-carboline ring (Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; 1987, 26: 757-760); 3) Using ammonium persulfate or sodium persulfate as oxidant, in nitric acid Under the

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Weigh 2.0g (9.26mmol) of tetrahydro-β-carboline-3-carboxylic acid into a 50ml multi-necked bottle, put it in a cold trap, cool down to below 0°C, and add sodium hydroxide solution (NaOH: 9.26mmol) to make it completely dissolved, then slowly add 1.2ml of hydrogen peroxide with a mass fraction of 30% (H 2 o 2 : 9.26mmol), after the addition, keep warm at 0°C, monitor the reaction process by TLC, spot the plate to confirm that the reaction raw material point disappears, stop the reaction, add dilute acid to the reaction solution to adjust the pH to neutral, extract three times with chloroform, wash with water , the organic phase was dried with anhydrous sodium sulfate, filtered with suction, and the filtrate was evaporated to remove the solvent to obtain 1.40 g of a yellow solid. The purity is 97%, and the yield is 90%.

Embodiment 2

[0015] Weigh 2.0g (9.26mmol) of tetrahydro-β-carboline-3-carboxylic acid into a 50ml multi-necked bottle, put it in a cold trap, cool down to below 0°C, and add sodium hydroxide solution (NaOH: 9.26mmol to make it completely dissolved, then slowly add 2.4ml of hydrogen peroxide (H 2 o 2 : 18.50mmol), after the addition, keep warm at 0°C for reaction, monitor the reaction process by TLC, spot the plate to confirm that the reaction raw material point disappears, stop the reaction, add dilute acid to the reaction solution to adjust the pH to neutral, extract three times with chloroform, wash with water , the organic phase was dried with anhydrous sodium sulfate, filtered with suction, and the filtrate was evaporated to remove the solvent to obtain 1.40 g of a yellow solid. The purity is 97%, and the yield is 95%.

Embodiment 3

[0017] Weigh 4.0g (18.50mmol) of tetrahydro-β-carboline-3-carboxylic acid into a 100ml multi-necked bottle, put it in a cold trap, cool down to below 0°C, and add potassium hydroxide solution (KOH: 18.50mmol) to make it completely dissolved, then slowly add 2.4ml of hydrogen peroxide with a mass fraction of 30% (H 2 o 2 : 18.50mmol), after the addition, keep warm at 0°C for reaction, monitor the reaction process by TLC, spot the plate to confirm that the reaction raw material point disappears, stop the reaction, add dilute acid to the reaction solution to adjust the pH to neutral, extract three times with chloroform, wash with water , the organic phase was dried with anhydrous sodium sulfate, filtered with suction, and the filtrate was evaporated to remove the solvent to obtain 2.86 g of a yellow solid. The purity is 97%, and the yield is 91%.

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Abstract

The invention discloses a green synthetic method of a beta-carboline compound. The green synthetic method of the beta-carboline compound is technically characterized by comprising the following steps: carrying out Pictet-Spengler reaction on L-tryptophan to prepare tetrahydro-beta-carboline-3-carboxylic acid; and decarboxylating and oxidizing the tetrahydro-beta-carboline-3-carboxylic acid under the effect of an oxidizing decarboxylating agent hydrogen peroxide to prepare the beta-carboline compound. The invention discloses specific synthetic steps and main reaction equations in the preparation process. The method disclosed by the invention has the advantages of simple preparation and safety and environmental-friendliness, and the yield of the beta-carboline compound is high, so that the demand on green chemistry is satisfied.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a green synthesis method of β-carboline compounds. Background technique [0002] Malignant tumor is a kind of cellular disease, the main feature is that the cell division is out of control, leading to uncontrolled growth, differentiation disorders, and invasion of local cells and metastasis, if not treated effectively, it will often hinder the function of normal organs, and even lead to die. At present, tumors have gradually replaced cardiovascular and cerebrovascular diseases as the number one killer of human beings. Now there are more than 20 million new cases in the world every year. There are about 1.8-2 million new cases in my country every year, about 1.5 million deaths, and more than 5 million patients. Cancer has also become the main reason why my country's working-age labor force loses their ability to work. At present, the main treatment methods are: surgery, radiat...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 张玮玮姜玉钦过治军郭利兵胡志国
Owner HENAN NORMAL UNIV
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