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N-N axial chiral pyrrole derivative and synthesis method thereof

A technology of pyrrole derivatives and synthesis methods, which can be applied in the fields of drug combination, asymmetric synthesis, organic chemistry methods, etc., can solve the problems of limited types of N-N-axis chiral pyrrole derivatives, and no one has studied the cytotoxicity of QGP-1 tumor cells. , to achieve the effect of broadening the scope of application, high yield and strong cytotoxic activity

Active Publication Date: 2022-05-24
XUZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the types of N-N axis chiral pyrrole derivatives are very limited, only limited to dynamic kinetic resolution and desymmetry reactions. No one has ever synthesized such compounds through the strategy of in-situ ring formation, and no one has studied the effects of these compounds on QGP- 1 Cytotoxicity of tumor cells

Method used

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  • N-N axial chiral pyrrole derivative and synthesis method thereof
  • N-N axial chiral pyrrole derivative and synthesis method thereof
  • N-N axial chiral pyrrole derivative and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] The synthetic route of N-N-axis chiral indole-pyrrole derivative 3aa is as follows:

[0025]

[0026] In above-mentioned reaction, the structural formula of catalyst chiral phosphoric acid is as follows:

[0027]

[0028] In 1 mL of carbon tetrachloride, 0.1 mmol of indoleamine 1a and 0.12 mmol of 1,4-diketone derivative 2a were added as reactants, and 0.01 mmol (10 mol% of indoleamine) of chiral phosphoric acid was used as a catalyst. The reaction was stirred at 25 °C for 5 h, followed by TLC to the end, filtered and concentrated, and purified and separated by silica gel column chromatography (eluent was a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 5:1) to obtain the NN axis. The yield and stereoselectivity of the chiral indole-pyrrole derivative 3aa are shown in Table 1.

[0029] Table 1 Effects of different kinds of chiral phosphoric acid on the reaction yield and stereoselectivity

[0030]

[0031] Note: In Table 1, ee is t...

Embodiment 2-15

[0036] The synthetic method of embodiment 2-15 is the same as that of embodiment 1, and the difference is that indoleamine with different structures is used as raw material, wherein the amount of chiral phosphoric acid in the reaction conditions of embodiment 2, 9, and 10 is indoleamine. of 20 mol%, and the reaction was stirred for 10 h.

[0037] Its reaction synthesis route is as follows:

[0038]

[0039] Product, productive rate and ee value are as shown in Table 2 below:

[0040] The product, productive rate and ee value of table 2 embodiment 1-15

[0041]

[0042]

[0043]

Embodiment 16-29

[0045] The synthetic methods of Examples 16-29 are the same as those of Example 1, except that 1,4-diketone derivatives of different structures are used as raw materials, and the amount of chiral phosphoric acid in the reaction conditions of Examples 16 and 25 is: 20mol% of indoleamine, and the reaction was stirred for 10h.

[0046] The reaction synthesis route is as follows:

[0047]

[0048] Product, productive rate and ee value are as shown in Table 3 below:

[0049] The reaction raw material, product, productive rate and ee value of table 3 embodiment 16-29

[0050]

[0051]

[0052]

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Abstract

The invention relates to an N-N axial chiral pyrrole derivative and a synthesis method thereof. The chemical structural formulas of the derivative are shown as a formula 3 and a formula 5; the preparation method comprises the following steps: by taking a 1, 4-diketone derivative and indoleamine or pyrrolamine as reaction raw materials, a molecular sieve as an additive and carbon tetrachloride as a reaction solvent, stirring and reacting under the catalysis of a chiral phosphoric acid catalyst, tracking the reaction by TLC until the reaction is complete, filtering, concentrating and purifying to obtain the indoleamine or pyrrolamine compound. According to the N-N axial chiral pyrrole derivative synthesized by the invention, a biological activity test shows that the derivative has relatively high sensitivity and very strong cytotoxic activity on QGP-1 tumor cells; chiral phosphoric acid is used as a catalyst, so that extremely high enantioselectivity is obtained. According to the method, reaction conditions are relatively conventional, the reaction process is mild, simple and convenient, the cost is low, the method is suitable for industrial large-scale production, and the application range of the method is widened; various substrates are used as reactants, products with various structures are obtained, and the yield and stereoselectivity are high.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to an N-N-axis chiral pyrrole derivative and a synthesis method thereof. Background technique [0002] Pyrrole derivative compounds widely exist in anticancer drug molecules and natural products, and have broad application prospects in the field of life sciences. It is often an enantiomer in the racemate that plays a biologically active role in drug molecules. Therefore, it is of great value to synthesize chiral pyrrole derivatives and conduct antitumor activity screening. At present, the types of N-N-axis chiral pyrrole derivatives are very limited, only limited to dynamic kinetic resolution and desymmetrization reactions. Such compounds have never been synthesized by in situ cyclization strategies, and no one has studied the effect of these compounds on QGP- 1 Cytotoxicity of tumor cells. SUMMARY OF THE INVENTION [0003] One of the objectives of the present invention...

Claims

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Application Information

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IPC IPC(8): C07B53/00C07D403/04C07D493/04A61P35/00
CPCC07B53/00C07D403/04C07D493/04A61P35/00C07B2200/07Y02P20/55
Inventor 石枫张宇辰陈志寒陈科伟
Owner XUZHOU NORMAL UNIVERSITY
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