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Method for synthesizing tetrahydro-beta-carboline diketopiperazine compound

A carboline diketopiperazine and a synthesis method technology, applied in the direction of organic chemistry and the like, can solve the problems of difficult separation of enantiomers, incomplete reaction, long reaction time, etc., and achieve short reaction steps, simple reaction conditions, and conversion rate. and high yield

Inactive Publication Date: 2011-12-14
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this synthetic route has the disadvantages of longer reaction time, incomplete reaction, difficult separation of enantiomers, and difficulty in purification.

Method used

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  • Method for synthesizing tetrahydro-beta-carboline diketopiperazine compound
  • Method for synthesizing tetrahydro-beta-carboline diketopiperazine compound

Examples

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Embodiment 1

[0031] (1) Reflux 6h of L-tryptophan methyl ester hydrochloride and aldehyde in n-butanol, the molar ratio of said L-tryptophan methyl ester hydrochloride and aldehyde is 1: 1.2, and said aldehyde is Benzaldehyde, carry out TLC follow-up in the described reflux, the developer of TLC follow-up is made up of chloroform and methanol, and the volume ratio of chloroform and methanol is 10: 1, after reflux completes, evaporate to dryness under reduced pressure to obtain powdery solid, solid with toluene Rinse to remove unreacted aldehyde, dry the solid after rinsing in a vacuum oven to obtain mixed enantiomer hydrochloride; (2) mix nitromethane and toluene to obtain inducer, use mixed enantiomer hydrochloride The inducer was refluxed for 24h, and the volume ratio of nitromethane and toluene in the step (2) was 1: 15. After reflux, the natural cooling allowed the solid to separate out, and realized the crystallization-induced asymmetric transformation (CIAT) process to make it to a si...

Embodiment 2

[0033] (1) Reflux 6h of L-tryptophan methyl ester hydrochloride and aldehyde in n-butanol, the molar ratio of said L-tryptophan methyl ester hydrochloride and aldehyde is 1: 1.2, and said aldehyde is Vanillin, carry out TLC tracking in the described reflux, the developing agent of TLC tracking is made up of chloroform and methanol, and the volume ratio of chloroform and methanol is 10: 1, evaporates to dryness under reduced pressure after reflux completes to obtain powdery solid, and solid is washed with toluene. Rinse to remove unreacted aldehyde, dry the solid after rinsing in a vacuum oven to obtain mixed enantiomer hydrochloride; (2) mix nitromethane and toluene to obtain inducer, use mixed enantiomer hydrochloride Inducer reflux 12, the volume ratio of nitromethane and toluene in the step (2) is 2: 3, after reflux, natural cooling makes solid precipitation, realizes crystallization-induced asymmetric transformation (CIAT) process and makes it to single enantiomer Conversi...

Embodiment 3

[0035] (1) Reflux 5h of L-tryptophan methyl ester hydrochloride and aldehyde in n-butanol, the mol ratio of said L-tryptophan methyl ester hydrochloride and aldehyde is 1: 1, and said aldehyde is Benzaldehyde, carry out TLC follow-up in the described reflux, the developer of TLC follow-up is made up of chloroform and methanol, and the volume ratio of chloroform and methanol is 10: 1, after reflux completes, evaporate to dryness under reduced pressure to obtain powdery solid, solid with toluene Rinse to remove unreacted aldehyde, dry the solid after rinsing in a vacuum oven to obtain mixed enantiomer hydrochloride; (2) mix nitromethane and toluene to obtain inducer, use mixed enantiomer hydrochloride The inducer was refluxed for 16 hours, and the volume ratio of nitromethane and toluene in the step (2) was 1.5:9. After reflux, the natural cooling allowed the solid to precipitate out, and the crystallization-induced asymmetric transformation (CIAT) process made it convert to a si...

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Abstract

The invention provides a method for synthesizing a tetrahydro-beta-carboline diketopiperazine compound. The method comprises the following steps of: reacting Pictet-Spengler reaction on L-tryptophane methyl ester hydrochloride serving as a starting raw material with aldehyde; performing a crystallization induced asymmetric transformation (CIAT) process to obtain a tetrahydro-beta-carboline ring; performing Schotten-Baumann reaction in a two-phase solvent comprising saturated sodium carbonate and dichloromethane; and finally forming an amido bond and performing a deprotection process to obtaina target product. The method has the beneficial effects of fewer reaction steps, high transformation rate and yield, advanced technological line, simple post-treatment, easiness in purification and the like.

Description

technical field [0001] The invention relates to a synthesis method of tetrahydro-β-carboline diketopiperazine compounds. Background technique [0002] Tetrahydro-β-carboline diketopiperazines, as a class of indole alkaloids, are widely distributed in nature. Studies have found that these compounds are selective inhibitors of breast cancer cells (BCRP / ABCG2) , can make the cell cycle stay in the G2 / M transition stage, because of its unique clinical drug resistance, making it the most interesting chemosensitizer. Therefore, the synthesis of this type of compound with unique structure and important biological activity has become a research hotspot. The main structure of this type of compound is formed by the interconnection of tetrahydro-β-carboline and diketopiperazine. About its synthesis report, Mainly through the three processes of Pictet-Spengler reaction, Schotten-Baumann reaction and amide bond formation. Through research, it is found that the main thing that really aff...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22
Inventor 马养民李延超张弘弛郑敬海闫倩茹郭会
Owner SHAANXI UNIV OF SCI & TECH
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