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Spiro indole diketopiperazine alkaloid, and synthesis method and application of spiro indole diketopiperazine alkaloid

A technology for indole diketopiperazine and a synthesis method, which is applied in the production of bulk chemicals, organic chemistry, antibacterial drugs, etc., can solve the problems of complex reaction route, cumbersome post-processing and high cost, and achieves improved reaction yield, The processing process is convenient and the effect of reducing the dosage

Active Publication Date: 2013-12-11
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis of such alkaloids mainly adopts methods such as free radical addition to form a ring, metal complexes participating in [5+2] cycloaddition, and 1,3-dipolar cycloaddition. Although these methods have successfully constructed Spiral ring structure and the connection of indole and diketopiperazine units, but most of the methods have defects such as high cost, complicated reaction route, low yield, and cumbersome post-treatment

Method used

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  • Spiro indole diketopiperazine alkaloid, and synthesis method and application of spiro indole diketopiperazine alkaloid
  • Spiro indole diketopiperazine alkaloid, and synthesis method and application of spiro indole diketopiperazine alkaloid
  • Spiro indole diketopiperazine alkaloid, and synthesis method and application of spiro indole diketopiperazine alkaloid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Add 50 mL of isopropanol to a 100 mL three-necked flask equipped with a stirrer, a constant-pressure dropping funnel, and a condensation reflux device, then add 12 mmol of propionaldehyde to the three-necked flask under stirring, and after stirring and mixing evenly, add 10 mmol of L-tryptophan methyl ester hydrochloride, then heated to a reflux state to react, during the reflux reaction process, TLC was used to monitor the progress of the reaction, and the reaction was carried out for 4 h. At this time, TLC detected that the raw material point of L-tryptophan methyl ester hydrochloride disappeared and Generate two new product points, end the reaction, evaporate isopropanol and excess propionaldehyde under reduced pressure to obtain solid A, which is rinsed with toluene to remove soluble impurities, and then dried to obtain mixed enantiomer hydrochloride (cis-trans mixture of mix-2a-HCl); wherein, the developing agent of TLC is mixed by ethyl acetate and methanol whos...

Embodiment 2

[0049] 1) Add about 50 mL of isopropanol to a 100 mL three-necked flask equipped with a stirrer, a constant pressure dropping funnel, and a condensing reflux device, then add 12 mmol of n-butyraldehyde to the three-necked flask under stirring, and after stirring and mixing evenly, add 10 mmol of L-tryptophan methyl ester hydrochloride was heated to a reflux state to react, and TLC was used to monitor the reaction during the reflux reaction, and the reaction was carried out for 4 h. At this time, TLC detected the raw material point of L-tryptophan methyl ester hydrochloride. Disappear and generate two new product points, finish the reaction, evaporate isopropanol and excess n-butyraldehyde under reduced pressure to obtain solid A, which is rinsed with toluene to remove soluble impurities, and then dried to obtain mixed enantiomers The hydrochloride salt (cis-trans mixture of mix-2b-HCl).

[0050] 2) Mix nitromethane and toluene uniformly in a volume ratio of 1:1 to obtain an in...

Embodiment 3

[0065] 1) Add 50 mL of isopropanol to a 100 mL three-necked flask equipped with a stirrer, a constant-pressure dropping funnel, and a condensing reflux device, then add 12 mmol of n-valeraldehyde to the three-necked flask under stirring, and after stirring and mixing evenly, add 10 mmol of L-tryptophan methyl ester hydrochloride, then heated to a reflux state to react, during the reflux reaction process, TLC was used to monitor the progress of the reaction, and the reaction was carried out for 4 h. At this time, TLC detected that the raw material point of L-tryptophan methyl ester hydrochloride disappeared and Generate two new product points, finish the reaction, evaporate isopropanol and excess n-valeraldehyde under reduced pressure to obtain solid A, which is rinsed with toluene to remove soluble impurities, and then dried to obtain mixed enantiomer hydrochloric acid Salt (cis-trans mixture of mix-2c-HCl); wherein, the developing agent of TLC is formed by mixing ethyl acetate...

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Abstract

The invention relates to spiro indole diketopiperazine alkaloid, and a synthesis method and an application of the spiro indole diketopiperazine alkaloid. The synthesis method comprises the steps that L-tryptophan methyl ester hydrochloride and fatty aldehyde perform Pictet-Spengler reaction to form enantiomeric hydrochloride, an inducer for inducing asymmetric conversion through crystallization induces the asymmetric conversion to form a single-configuration product, the single-configuration product performs Schotten-Baumann reaction to form an amido bond, then a spiral structure is obtained by NBS (N-bromosuccinimide) rearrangement, a protecting group is removed from the spiral structure under base catalysis, and the spiral structure is subjected to ring closing to form the spiro indole diketopiperazine alkaloid. The method has the advantages that the method is low in cost, simple and convenient in path, high in yield and easy to process, an end product and a natural product are the same in configuration, etc. The prepared spiro indole diketopiperazine alkaloid can be further applied to preparation of antibiotics.

Description

technical field [0001] The invention relates to the field of total synthesis of natural alkaloids, in particular to a spirocyclic indole diketopiperazine alkaloid and a synthesis method and application thereof. Background technique [0002] Spirocyclic indole diketopiperazine alkaloids, as indole alkaloids with special structure, are widely distributed in nature, especially in the form of fungal secondary metabolites. The study found that this alkaloid can inhibit mouse breast cancer cells (tsFT210) in the G2 / M phase, and confirmed its effect on human chronic myeloid leukemia (K562) cells and human promyelocytic leukemia (HL-60) Cell lines such as cells have cytotoxic activity. It is also reported that some such compounds also have anti-HIV, antibacterial, insect tremor and other activities. Based on the above characteristics, in recent years, there have been many reports on its synthesis. At present, the synthesis of such alkaloids mainly adopts radical addition to form ...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61P31/04A61P31/10
CPCY02P20/55
Inventor 马养民吴昊任德成张金李延超张弘弛
Owner SHAANXI UNIV OF SCI & TECH
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