Compound as well as preparation method and application thereof

A compound and heterocyclic compound technology, applied in the field of medicine, can solve problems such as unsatisfactory curative effect and anticancer drugs that need to be deepened, and achieve the effect of increasing yield, improving yield and reaction efficiency, and inhibiting cell proliferation

Inactive Publication Date: 2014-07-02
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Drugs designed with DNA and related enzymes as targets are current research hotspots. Some drugs have been used for cancer treatment or have entered the clinical research stage, such as large aromatic ring anti-tumor drugs, etc., but the curative effect is still unsatisfactory
[0003] Therefore, the research on anticancer drugs still needs to be deepened

Method used

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  • Compound as well as preparation method and application thereof
  • Compound as well as preparation method and application thereof
  • Compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Preparation of 9-[(2-benzimidazolyl)-methyl]-2-methoxy-acridin-9-amine

[0060] 1. Preparation of 2-(4-methoxyphenylamino)benzoic acid

[0061] Add 2-chlorobenzoic acid (1.00g, 5.23mmol), 4-methoxyaniline (0.86g, 6.99mmol), potassium carbonate (2.00g, 14.49mmol) in dimethylformamide (DMF, 50.00ml) and copper powder (0.20g, 3.15mmol), then stirred overnight at 130°C, then added to 200ml of water after the resulting reaction mixture was cooled, the resulting mixture was adjusted to a pH value of about 3 with hydrochloric acid, suction filtered and The obtained precipitate was dried to obtain an off-white solid, namely 2-(4-methoxyphenylamino)benzoic acid, and the product was directly carried out to the next reaction without further purification.

[0062] 2. Preparation of 9-chloro-2-methoxyacridine

[0063] The 2-(4-methoxyphenylamino)benzoic acid (2.00g, 7.19mmol) obtained in step 1 was added to anhydrous phosphorus oxychloride (10.00ml), and refluxed at 110...

Embodiment 2

[0070] Embodiment 2: Preparation of 9-[(2-benzimidazolyl)-methyl]-acridine-9 amine

[0071] 9-chloroacridine (1 mmol) and 2-aminomethylbenzimidazole (1.2 mmol) were added to 2 g of phenol, stirred at 120° C. for 2 hours, and then 100 ml of ethyl acetate was added to the resulting reaction solution to produce A large amount of precipitation was filtered, and the resulting precipitate was washed with ether to obtain 9-[(2-benzimidazolyl)-methyl]-acridine-9amine (ie, the compound shown in formula 1).

[0072] Yield 32%; melting point 262°C; high-resolution mass spectrum (ESI): calculated value [M+H]+325.1453; experimental value: 325.1447.

[0073] The confirmed data of the compound structure are:

[0074] 1 H NMR(400MHz,DMSO)δ8.66(d,J=8.1Hz,2H),7.98(d,J=13.8Hz,4H),7.54(d,J=16.2Hz,4H),7.19(dd,J =6.0,3.0Hz,2H),5.54(s,2H).

Embodiment 3

[0075] Example 3: Preparation of 9-[(2-benzoimidazolyl)-methyl]-6-chloro-2-methoxy-acridin-9-amine

[0076] 6,9-Dichloro-2-methoxy-acridine (1mmol) and 2-aminomethylbenzimidazole (1.2mmol) were added to 2g of phenol, stirred at 120°C for 2 hours, and then to the obtained 100ml of ethyl acetate was added to the reaction solution to produce a large amount of precipitate, which was filtered by suction and washed with ether to obtain 9-[(2-benzoimidazolyl)-methyl]-6-chloro-2-methoxy- Acridin-9-amine (i.e. the compound shown in formula 3).

[0077] Yield 22%; melting point 237°C; high-resolution mass spectrum (ESI): calculated value [M+H]+389.1169; experimental value: 389.1163.

[0078] The confirmed data of the compound structure are:

[0079] 1 H NMR(400MHz,DMSO)δ8.66(d,J=8.1Hz,2H),7.98(d,J=13.8Hz,4H),7.54(d,J=16.2Hz,4H),7.19(dd,J =6.0,3.0Hz,2H),5.54(s,2H)

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Abstract

The invention provides a compound as well as a preparation method and application thereof. The compound is a compound with the structural formula shown in Formula I or an acceptable salt, ester or solvate of the compound with the structural formula shown in Formula I which is shown in the specifications, wherein X is NHCH2, NHCH2CH2, NH, S or a substance with the formula shown in the specifications, R1, R2, R3 and R4 are independently H, F, Cl, OCH3, CF3 or a straight-chain alkyl with the carbon atoms of 1-5, and Y is 2-pyridyl, 4-pyridyl, 2-indolyl, naphthyl, anthryl, quinolyl, pyrimidinyl, furyl, thienyl or 2-benzimidazolyl. The compound of the invention can be used for restraining topoisomerase as well as the proliferation of eukaryote tumour cells, and preventing and / treat tumour.

Description

technical field [0001] The present invention relates to the field of medicine, in particular to compounds and their preparation methods and uses. Background technique [0002] Cancer is the number one cause of human death today, and the development of highly effective anticancer drugs is imminent. Drugs acting on DNA targets can interact with DNA to change the structure of DNA, such as unwinding the helical structure of DNA and extending DNA chains, etc., thereby delaying or inhibiting the transcription and translation of DNA. Drugs designed with DNA and related enzymes as targets are current research hotspots. Some drugs have been used for cancer treatment or have entered the clinical research stage, such as large aromatic ring anti-tumor drugs, etc., but the curative effect is still unsatisfactory. [0003] Therefore, the research on anticancer drugs still needs to be deepened. Contents of the invention [0004] The present invention aims to solve one of the technical ...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61K31/473A61P35/00A61P35/02
CPCC07D401/12C07D219/10
Inventor 蒋宇扬李彬高春梅孙钦生
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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