Substituted benzamide compounds and preparation method and application thereof

A technology of benzamides and compounds, applied in the field of application in the treatment of cancer, can solve problems such as proliferative diseases

Inactive Publication Date: 2012-07-04
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, overexpression of normal proto-oncogenic

Method used

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  • Substituted benzamide compounds and preparation method and application thereof
  • Substituted benzamide compounds and preparation method and application thereof
  • Substituted benzamide compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1: N-(3-bromophenyl)-2-hydroxyl-5-bromoacetamidobenzamide

[0105]

[0106] Preparation of N-(3-bromophenyl)-2-acetoxy-5-nitrobenzamide:

[0107] Take 5-nitrosalicylic acid (1.83g, 10mmol) and acetic anhydride (4.08g, 40mmol) in a flask, add 2 drops of concentrated sulfuric acid dropwise, gradually heat up to 85-90°C under slow stirring, and react for 5h. After cooling and filtering, the solid was washed with cold water, a small amount of saturated NaHCO3 solution, and water, and dried to obtain 1.75 g of 5-nitro-2-acetoxybenzoic acid light yellow solid powder with a yield of 77.8% and a melting point of 161-162°C. Take 5-nitro-2-acetoxybenzoic acid (1.125g, 5mmol), add appropriate amount of SOCl 2 , heated to reflux for 3h, evaporated under reduced pressure to remove excess SOCl 2 , to obtain an oily substance, add an appropriate amount of ethyl acetate to dissolve, slowly add 3-chloroaniline (0.86g, 5mmol) and an appropriate amount of triethylamine in eth...

Embodiment 2

[0115] Example 2: N-(3-bromophenyl)-2-hydroxyl-5-chloroacetamidobenzamide.

[0116]

[0117] Preparation of N-(3-bromophenyl)-2-acetoxy-5-chloroacetamidobenzamide:

[0118] Take N-(3-bromophenyl)-2-acetoxy-5-aminobenzamide (0.524g, 1.5mmol), add an appropriate amount of ethyl acetate to dissolve, add a few drops of triethylamine, and place in an ice-water bath chloroacetyl chloride (0.17g, 1.5mmol) was slowly added dropwise, and the reaction solution became cloudy. After the dropwise addition, it was reacted at room temperature for 1 hour, and the precipitate was filtered off. NaCl solution, followed by anhydrous NaCl 2 SO 4 After drying, the solvent was distilled off under reduced pressure, and recrystallized from ethyl acetate-petroleum ether to obtain 0.419 g of khaki solid powder with a yield of 65.6%.

[0119] Preparation of N-(3-bromophenyl)-2-hydroxyl-5-chloroacetamidobenzamide:

[0120] Take N-(3-bromophenyl)-2-acetoxy-5-chloroacetamidobenzamide (0.524g, 1.5mmol...

Embodiment 3

[0122] Example 3: N-((S)-1-phenylethyl)-2-hydroxyl-5-bromoacetamidobenzamide.

[0123]

[0124] Preparation of N-((S)-1-phenethyl)-2-acetoxy-5-nitrobenzamide:

[0125] Take 5-nitro-2-acetoxybenzoic acid (1.21g, 10mmol), add appropriate amount of SOCl 2 , heated to reflux for 3h, evaporated under reduced pressure to remove excess SOCl 2 , to obtain an oily substance, add an appropriate amount of ethyl acetate to dissolve, and slowly add (S)-1 phenylethylamine (1.21g, 10mmol) and an appropriate amount of triethylamine in ethyl acetate solution dropwise under ice-water bath, and dropwise Afterwards, react at room temperature for 1 h, filter, and the filtrate is washed with 1mol / l hydrochloric acid, 10% sodium bicarbonate solution, saturated NaCl solution, and then washed with anhydrous Na 2 SO 4 After drying, the solvent was distilled off under reduced pressure, and the resultant was recrystallized from ethyl acetate-petroleum ether to obtain 2.79 g of white needle crystals...

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Abstract

The invention relates to substituted benzamide compounds shown as a general formula (I) or medicinal salts thereof, preparation of the compounds or the medicinal salts thereof, a medicament composition containing the compounds or the medicinal salts thereof and application of the compounds in treatment of cancers, in particular application in treatment of head and neck cancers, non-small cell lung cancer, pancreatic cancer, colorectal cancer, bladder cancer, breast cancer, ovarian cancer and flat cell cancer and application in medicaments for treating the cancers.

Description

technical field [0001] The present invention relates to a substituted benzamide compound represented by the following formula I and a pharmaceutically acceptable salt thereof, the preparation of the compound, the pharmaceutical composition containing them and the application of the compound in the treatment of cancer. [0002] Background technique [0003] At present, the incidence of cancer is gradually increasing, while the cure rate is still relatively low. Chemotherapy is an important means to inhibit tumor growth and spread of cancer cells, and to eliminate tumors. Most of the traditional chemotherapeutic drugs are cytotoxic drugs that directly attack DNA or inhibit its synthesis and function. They kill both cancer cells and normal cells. They are only effective for fast-growing tumors and have strong side effects. In order to increase the selectivity of action on cancer cells, another route of anticancer agents that does not pass through the mechanism of inhibiting...

Claims

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Application Information

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IPC IPC(8): C07C237/44C07C231/12C07C309/66C07C303/30C07D295/088A61K31/255A61K31/167A61K31/222A61K31/5375A61P35/00
CPCY02P20/55
Inventor 冯志强陈晓光黄海刘振佳周晴
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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