N-(3-(3-chlorobenzamide) phenyl)-4-methoxy-3-nitrobenzamide and preparation method and application thereof

A technology of nitrobenzamide and chlorobenzamide, which is applied in the field of compound synthesis, can solve the problem of lack of high-efficiency and specific clinical treatment drugs for colon cancer, achieve inhibition of proliferation and growth, simple preparation method, and easy-to-obtain preparation raw materials Effect

Active Publication Date: 2022-07-15
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chemotherapy mainly uses general chemotherapy drugs such as fluorouracil (5-fluorouracil and capecitabine), mitomycin and doxorubicin, and there is a lack of effective and specific clinical drugs for colon cancer

Method used

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  • N-(3-(3-chlorobenzamide) phenyl)-4-methoxy-3-nitrobenzamide and preparation method and application thereof
  • N-(3-(3-chlorobenzamide) phenyl)-4-methoxy-3-nitrobenzamide and preparation method and application thereof
  • N-(3-(3-chlorobenzamide) phenyl)-4-methoxy-3-nitrobenzamide and preparation method and application thereof

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Embodiment 1

[0042] This example describes N-(3-(3-chlorobenzamide)phenyl)-4methoxy-3-nitrobenzamide and its preparation method. The N-(3-(3-chlorobenzamide) The structural formula of carboxamide) phenyl)-4-methoxy-3-nitrobenzamide is as follows figure 1 As shown, the preparation method of this N-(3-(3-chlorobenzamide) phenyl)-4 methoxyl group-3-nitrobenzamide is as follows:

[0043]

[0044] Wherein, the molar ratio of m-phenylenediamine, triethylamine and m-chlorobenzoyl chloride is 1:2:1, 3-nitro-4-methoxybenzoic acid, N,N-diisopropylethylamine, The molar ratio of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride was 1:2:2.

[0045] Specifically, the preparation method of this N-(3-(3-chlorobenzamide)phenyl)-4methoxy-3-nitrobenzamide is illustrated below:

[0046] Dissolve 2.16 g m-phenylenediamine (20 mmol) in 100 mL of dichloromethane, add 5.5 mL of triethylamine under an ice bath to obtain a mixed solution 1, and dissolve 3.5 g of m-chlorobenzoyl chloride (20 mmol) in 20...

Embodiment 2

[0052] Example 2 Related Cell Tests

[0053] (1) Cell culture

[0054] HCT116, HT29, SW620, HEK293T and FHC used in this example were purchased from the American Type Culture Collection (ATCC, Virginia, USA). HCT116 was cultured in McCoy's 5A medium (SH30200.01, Hyclone), and HT29, SW620, HEK293T and FHC were cultured in high-glucose DMEM medium (SH30022.01, Hyclone) at 37°C, Contains 5% CO 2 in a humidified incubator and supplemented with 10% fetal bovine serum (FBS, 10100147, Gibco) and 1% penicillin-streptomycin.

[0055] (2) Plasmid transfection and lentivirus infection

[0056] Plasmid constructs expressing T7-SKP2 and Myc-SKP2 were obtained from Shandong Weizhen Biotechnology Co., Ltd. Use Lipo8000 according to manufacturer's protocol TM Transfection reagents (Beyotime) were used to transfect cells with the indicated plasmids. For stable transfection, use Lipo8000 TM Transfection Reagent Co-transfection of targeting plasmids, Pspax2 and pMD2G vectors into HEK293T ...

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Abstract

The invention relates to the technical field of compound synthesis, in particular to N-(3-(3-chlorobenzamide) phenyl)-4-methoxy-3-nitrobenzamide and a preparation method and application thereof.The preparation method comprises the steps that m-phenylenediamine, triethylamine and m-chlorobenzoyl chloride serve as main raw materials to react, and an intermediate product is obtained; the preparation method comprises the following steps: dissolving 3-nitro-4-methoxybenzoic acid in dichloromethane, sequentially adding N, N-diisopropylethylamine and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, dissolving an intermediate product in dichloromethane while stirring, adding the intermediate product, stirring at room temperature for reaction, sequentially cleaning an obtained reactant with diluted hydrochloric acid and clear water, and drying to obtain the 3-nitro-4-methoxybenzoic acid. And drying the washed organic phase by anhydrous sodium sulfate, spin-drying, and passing through a column by using silica gel to obtain N-(3-(3-chlorobenzamide) phenyl)-4-methoxy-3-nitrobenzamide. The N-(3-(3-chlorobenzamide) phenyl)-4-methoxy-3-nitrobenzamide provided by the invention can obviously inhibit the activity and proliferation growth of HCT116 and HT29 cells, and can be applied to the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to N-(3-(3-chlorobenzamide)phenyl)-4methoxy-3-nitrobenzamide and a preparation method and application thereof. Background technique [0002] Colorectal cancer is one of the common tumors in my country, including rectal cancer and colon cancer, and it is also one of the tumors with the fastest increasing incidence in the past two or three decades. 4, 5 or 6, the incidence rate in our country is about 24 / 100,000, and male is slightly higher. With the development of the economy, the improvement of living standards and the change of lifestyle, the incidence rate will continue to rise. [0003] Many colorectal cancer epidemiological studies have shown that there are many factors that cause colorectal cancer, such as dietary factors, occupational factors, physical activity, genetic factors, disease factors and other carcinogenic factors. The occurrence and development of colon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/56C07C231/14C07C231/02C07C233/80A61P35/00
CPCC07C235/56C07C231/14C07C231/02A61P35/00C07C233/80Y02P20/55
Inventor 杨东林何刘军李勇张亚军黄玖红胡春生
Owner CHONGQING UNIV OF ARTS & SCI
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