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A kind of indole compound and its synthesis method and application

A synthesis method and compound technology, applied in the field of indole compounds and their synthesis, can solve problems such as the inability to overcome the drug resistance of tumor cells, and achieve the effects of small side effects, good inhibitory effect, and good resistance to drug resistance

Active Publication Date: 2021-10-01
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The AR inhibitors used clinically today all target LBD, so they cannot overcome the problem of AR-VS-driven tumor cell drug resistance

Method used

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  • A kind of indole compound and its synthesis method and application
  • A kind of indole compound and its synthesis method and application
  • A kind of indole compound and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0047] The present invention also provides a kind of synthetic method of indole compound, comprising:

[0048]The compound of formula (II) structure, palladium acetate, benzoquinone compound and organic acid are dissolved in solvent and reacted to obtain the compound of formula (I) structure;

[0049]

[0050] where the R 1-2 , R 1-4 , R 1-6 independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy;

[0051] The R 1-3 , R 1-5 independently selected from hydrogen or halogen;

[0052] and the R 1-2 , R 1-3 , R 1-4 , R 1-5 , R 1-6 not simultaneously hydrogen;

[0053] The R 2-0 selected from hydrogen, C1-C5 methyl or C1-C5 methoxy;

[0054] The R 2-2 selected from hydrogen, C1-C6 methyl or C1-C6 methoxy;

[0055] The R 2-3 selected from hydrogen, C1-C6 methyl or C1-C6 methoxy;

[0056] The R 2-4 selected from hydrogen, C1-C6 methyl or C1-C6 methoxy;

[0057] The R 2-5 selected from hydrogen, C1-C6 methoxy or halogen;

[0058] The R 2-6 selected from...

preparation example

[0076] 1) The preparation of intermediate allylaniline compounds, taking N-allylaniline as an example, is shown in the following formula:

[0077]

[0078] Aniline (1mmol) and K 2 CO 3 (1.5mmol) was added into anhydrous DMF, then allyl bromide (1mmol) was added dropwise, stirred for 12h, quenched with water, extracted with ethyl acetate, washed with saturated brine, anhydrous Na 2 SO 4 Drying and column separation (petroleum ether) gave N-allylaniline with a yield of 60% and a purity of 99.99%.

[0079] The obtained compound is identified, and its NMR results are as follows: 1 H NMR (500MHz, CDCl 3 )δ7.25–7.20(m,2H),6.93(t,J=7.4Hz,1H),6.80(d,J=7.9Hz,1H),6.12(dq,J=11.6,6.2Hz,1H), 5.29(t, J=13.2Hz, 2H), 3.78(s, 2H), 3.45(d, J=6.2Hz, 2H). 13 C NMR (126MHz, CDCl 3 )δ143.76(s), 134.89(s), 129.08(s), 126.46(s), 122.91(s), 117.76(s), 115.01(s), 114.74(s), 35.37(s).

[0080] 2) The preparation of intermediate 2-allyl aniline compounds, taking 2-allyl aniline as an example, ...

Embodiment

[0093] According to the preparation method provided in the preparation example, different raw materials are selected to obtain a series of R 1 and R 2 Indole compounds with different substituents are denoted as 5b~5u. The specific reaction process and the obtained products are shown in the following reaction process;

[0094]

[0095] The product detection that obtains to each step reaction, wherein, figure 2 is the hydrogen spectrum of allylaniline compound 2b, figure 2 It is the carbon spectrum of allylaniline compound 2b; image 3 is the hydrogen spectrum of allylaniline compound 3b, Figure 4 It is the carbon spectrum of allylaniline compound 3b; Figure 5 Be the hydrogen spectrum of N-(allylphenyl) benzamide compound 4k; Figure 6 Be the carbon spectrum of N-(allylphenyl) benzamide compound 4k; Figure 7 It is the hydrogen spectrum of indole compound 5k, Figure 8 It is the carbon spectrum of the indole compound 5k; specifically, the NMR data of the compound o...

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Abstract

The invention discloses an indole compound and its preparation method and application. The indole compound provided by the invention is found through experiments through the selection of specific substituents, as an anticancer drug, it has a good inhibitory effect on prostate cancer, And has good anti-drug resistance, and side effect is little; In addition, the synthetic method provided by the present invention, by reacting in solvent with the compound of formula (II), palladium acetate, benzoquinone compound and organic acid, The indole compound with the structure of formula (I) is obtained; the experimental results show that the method provided by the invention not only has relatively low requirements on the substrate, but also has a high yield of the obtained product.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an indole compound and its synthesis method and application. Background technique [0002] Tumor is a disease that seriously threatens human health. At present, the treatment of tumor is still mainly based on drug treatment. Therefore, it is of great significance to research and develop new antitumor drugs with high efficiency and low toxicity. Prostate cancer is the most common tumor in European and American men, and it is the second most lethal cancer in men. Although the incidence of prostate cancer in my country is far lower than that in Western countries, it has shown a significant increase in recent years. [0003] Prostate cancer initially relies primarily on androgens (AR) for growth. Clinically, there are generally three ways to treat prostate cancer: surgery, androgen-targeted therapy, and chemotherapy. Generally, androgen-targeted therapy mainly includes androgen ab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08A61P35/00A61K31/404
CPCA61P35/00C07D209/08
Inventor 赵德鹏王军舰常喆王红
Owner SUN YAT SEN UNIV
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