A kind of synthetic method and application of helical indole compound based on phenylalanine and polycarbonyl cyclic ketone compound

A technology for indoles and compounds, which is applied in the field of synthesizing spiro indole compounds, can solve the problems of complex synthesis steps, difficulty in operation, high price of reaction raw materials, etc., and achieves cheap and easy-to-obtain raw materials, environment-friendly and pollution-free reaction solvents, and the method. simple effect

Active Publication Date: 2020-12-22
WANNAN MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing synthetic techniques generally need to go through relatively complicated synthetic steps, and the price of reaction raw materials is relatively high, and there are many problems such as certain difficulty in operation.

Method used

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  • A kind of synthetic method and application of helical indole compound based on phenylalanine and polycarbonyl cyclic ketone compound
  • A kind of synthetic method and application of helical indole compound based on phenylalanine and polycarbonyl cyclic ketone compound
  • A kind of synthetic method and application of helical indole compound based on phenylalanine and polycarbonyl cyclic ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A kind of synthetic method based on the helical indole compound of phenylalanine, described synthetic method comprises the following steps:

[0038] (1) Weigh 1mmol 2-vinylpyridylindoline, 1mmol phenylalanine and 1mmol isatin respectively, place them in 50mL ethanol aqueous solution reaction solvent, and heat, stir and reflux for 3 hours under air environment;

[0039] (2) After the reaction finishes, wait until the temperature is cooled to room temperature, and the reaction product is suction filtered to obtain a solid crude product, and then the solid crude product is filtered with CH 3 OH / DMF mixed solvent was used for recrystallization, and after recrystallization twice, an orange-yellow solid, that is, pyridyl indoline compound 1 was obtained; the yield was 50%, and the melting point was 120-124°C.

[0040] The product structural formula of gained pyridyl indoline compound 1 is:

[0041]

[0042] H NMR spectrum data of the product:

[0043] 1 H NMR (400MHz, D...

Embodiment 2

[0047] A kind of synthetic method based on the helical indole compound of phenylalanine, described synthetic method comprises the following steps:

[0048] (1) Weigh 1mmol 2-vinylpyridyl indoline, 1mmol phenylalanine and 1mmol 4-nitro-isatin respectively, place them in 50mL of ethanol aqueous solution reaction solvent, and heat, stir and reflux under air environment for 3 Hour;

[0049] (2) After the reaction finishes, wait until the temperature is cooled to room temperature, and the reaction product is suction filtered to obtain a solid crude product, and then the solid crude product is filtered with CH 3 OH / DMF mixed solvent was used for recrystallization, and after recrystallization twice, a white solid, that is, pyridyl indoline compound 2 was obtained; the yield was 35%, and the melting point was 80-82°C.

[0050] The product structural formula of gained pyridyl indoline compound 2 is:

[0051]

[0052] H NMR spectrum data of the product:

[0053] 1 H NMR (400MHz, ...

Embodiment 3

[0057] A kind of synthetic method based on the helical indole compound of phenylalanine, described synthetic method comprises the following steps:

[0058] (1) Weigh 1mmol 2-vinylpyridylindoline, 1mmol phenylalanine and 1mmol acenaphthenequinone respectively, place them in 50mL ethanol aqueous solution reaction solvent, and heat, stir and reflux for 2 hours under air environment;

[0059] (2) After the reaction finishes, wait until the temperature is cooled to room temperature, and the reaction product is suction filtered to obtain a solid crude product, and then the solid crude product is filtered with CH 3 OH / DMF mixed solvent was used for recrystallization, and after recrystallization twice, an orange-yellow solid, that is, pyridyl indoline compound 3 was obtained; the yield was 63%, and the melting point was 86-87°C.

[0060] The product structural formula of gained pyridyl indoline compound 3 is:

[0061]

[0062] H NMR spectrum data of the product:

[0063] 1 H NMR...

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Abstract

The invention discloses a synthesis method for spiral indole compounds based on phenylalanine and multi-carbonyl-class cyclic ketone compounds. The method comprises the steps that pyridyl-class indolecompounds, phenylalanine and multi-carbonyl-class cyclic ketone compounds are subjected to addition and condensation reaction in an alcohol aqueous solution, high-yield spiral indole compounds are obtained, and then extraction filtration and recrystallization are conducted to obtain purified products. Compared with the prior art, the synthesis method is simple and convenient, original multi-stepreaction is replaced by a single-pot synthesis method, raw materials are easily obtained, the reaction efficiency is high, and the method is suitable for multiple reaction substrates; the spiral indole compounds have the medicine activity at the same time and can be applied to medicine for effective clinical treatment of tumors and cancer.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method and application of a helical indole compound based on phenylalanine and polycarbonyl cyclic ketone compounds. Background technique [0002] It has been reported that spirooxindole compounds can be used as inhibitors of P53-MDM2. These small molecular compounds can be used as a drug for tumor treatment, directly targeting tumor cells without affecting normal cells. In the past few years, major advances have been made in synthetic methods to obtain helical indole derivatives in a manner that simultaneously creates a chiral quaternary carbon center. For example, Overman reported an asymmetric intramolecular Heck reaction to synthesize spiro-pyrrole-3,3'-indole] derivatives with high enantioselectivity; (references V.Caprio, B.Guyen, Y. Opoku-Boahen, J. Mann, S.M. Gowan, L.M. Kelland, M.A. Read and S. Neidle, Bio. Med. Chem. Lett., 2000, 10, 2063-2066....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/10A61P35/00
CPCC07D487/10
Inventor 颜亮王毅马金珠徐蕾章尧聂刘旺
Owner WANNAN MEDICAL COLLEGE
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