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A kind of benzo five-member nitrogen heterocycle derivative and its application

A five-membered nitrogen heterocycle and derivative technology, applied in the field of organic compounds, can solve the problems of not being able to take it orally, having high toxic and side effects, and only being able to be administered by injection

Active Publication Date: 2022-04-05
GUANGDONG CHENKANG BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problems that exist are: 1. large toxic and side effects; 2. easy to produce drug resistance (multidrug resistance / MDR); 3. only injection administration, not oral

Method used

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  • A kind of benzo five-member nitrogen heterocycle derivative and its application
  • A kind of benzo five-member nitrogen heterocycle derivative and its application
  • A kind of benzo five-member nitrogen heterocycle derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 (Preparation of RYC-1)

[0045] The structural formula of the benzofive-membered nitrogen heterocyclic derivative prepared in this example is:

[0046] The preparation method of compound shown in above-mentioned formula (RYC-1) consists of the following steps:

[0047] Step 1: Preparation of Compound IIa

[0048] The structural formula is prepared according to the following method: compound of:

[0049]

[0050] Take (1.0 g, 4.13 mmol) 3-bromo-5 nitroindazole and dissolve it in 20 mL of acetonitrile, then add (947 mg, 4.34 mmol) BORYC-2O, (202 mg, 1.65 mmol) DMAP, (859 μL, 6.20 mmol) three Ethylamine was reacted at room temperature for 12h. The reaction was monitored by TLC, after the reaction was completed, the reaction solution was spin-dried, the concentrate was dissolved in ethyl acetate, and extracted once with saturated sodium bicarbonate and brine in turn. Ethyl acetate 9:1 column chromatography obtained solid 1.1 g with a yield of 79.2%. Th...

Embodiment 2

[0067] Example 2 (Preparation of RYC-2)

[0068] The structural formula of the benzofive-membered nitrogen heterocyclic derivative prepared in this example is:

[0069] The compound represented by the above formula (RYC-2) uses 3-bromo-5 nitroindazole, 3,4,5-trimethoxybenzeneboronic acid and 1-methylindazole-5-boronic acid as raw materials, and the specific preparation method is the same as Embodiment 1 is identical, and chemical reaction formula is as follows:

[0070]

[0071] The obtained product of above-mentioned method is identified by nuclear magnetic resonance spectrum, and the result is: 1 H NMR (400MHz, CDCl 3 )δ8.19(s, 1H), 8.07(s, 1H), 7.96(s, 1H), 7.75(d, J=8.7Hz, 1H), 7.72(d, J=8.7Hz, 1H), 7.61( d, J=8.6Hz, 1H), 7.52(d, J=8.7Hz, 1H), 7.25(s, 2H), 4.15(s, 3H), 3.99(s, 6H), 3.96(d, J=0.7 Hz, 3H).

Embodiment 3

[0072] Example 3 (Preparation of RYC-3)

[0073] The structural formula of the benzofive-membered nitrogen heterocyclic derivative prepared in this example is:

[0074] The compound shown in the above formula (RYC-3) uses 3-bromo-5 nitroindazole, 3,4,5-trimethoxybenzeneboronic acid and p-methylphenylboronic acid as raw materials, and the specific preparation method is the same as in Example 1, The chemical reaction formula is as follows:

[0075]

[0076] The obtained product of above-mentioned method is identified by nuclear magnetic resonance spectrum, and the result is: 1 H NMR (400MHz, CDCl 3 )δ8.16(s,1H),7.72(dd,J=8.7,1.4Hz,1H),7.60(d,J=8.8Hz,1H),7.56(d,J=8.1Hz,2H),7.31( d, J=7.9Hz, 2H), 7.23(s, 2H), 6.11(s, 1H), 3.99(s, 6H), 3.96(s, 3H), 2.44(s, 3H).

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Abstract

The present invention relates to a benzo five-membered nitrogen heterocyclic derivative, the chemical structure of the compound is shown in the following formula (I); in the formula (I), X is N or C; Y is C or N; R 1 is 1-methyl-indol-5-yl, 1-methyl-indazol-5-yl, 3,4,5-trimethoxyphenyl or p-methylphenyl; R 2 is 3,4,5-trimethoxyphenyl, p-methylphenyl, 1-methyl-indol-5-yl, 1-methyl-indol-4-yl or 1-methyl-indol ‑3‑base. The compound of the invention can inhibit the proliferation of tumor cells and can be used to prepare anti-tumor drugs.

Description

technical field [0001] The present invention relates to organic compounds, in particular to benzo five-membered nitrogen heterocyclic compounds, which can inhibit the proliferation of tumor cells and can be used to treat tumors. Background technique [0002] Cancer is one of the major diseases affecting human health. At present, the number of cancer patients is increasing year by year. In the future, it will surpass heart disease to become the number one killer of human death. At present, more than 100 anti-tumor drugs have been widely used in the treatment of cancer at home and abroad, and have significantly improved the survival rate of patients and the quality of life of patients. However, there are still many shortcomings in clinical treatment of anti-tumor drugs, such as The toxic and side effects are large, and the drug resistance and selectivity of cancer cells are low. Therefore, it is of great significance to design and synthesize anti-tumor drugs with low side effe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C07D231/56A61P35/00
CPCC07D403/04C07D231/56A61P35/00
Inventor 陈建军任益昌程斌斌
Owner GUANGDONG CHENKANG BIOTECHNOLOGY CO LTD