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Benzoyl hydrazone compounds with antineoplastic activity

A technology of benzoyl hydrazone and compound, applied in the application field of anti-tumor growth inhibitor, can solve the problems such as unmentioned anti-tumor activity

Inactive Publication Date: 2009-04-08
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] These compounds are reported to have high-efficiency bactericidal or insecticidal activity, but no anti-tumor activity is mentioned

Method used

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  • Benzoyl hydrazone compounds with antineoplastic activity
  • Benzoyl hydrazone compounds with antineoplastic activity
  • Benzoyl hydrazone compounds with antineoplastic activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of o-hydroxybenzoic hydrazide

[0028]

[0029] Add 1.38g (0.01mol) of p-salicylic acid and 32g (0.1mol) of methanol into a 50ml three-necked flask, and slowly add 3.0ml of concentrated sulfuric acid while stirring. Heat to reflux for 8 hours, distill off excess methanol, filter the raffinate to remove unreacted salicylic acid, wash the filtrate repeatedly with water to weak acidity, distill under reduced pressure, collect fractions at 84°C / 0.093kPa to obtain 1.31g of light yellow liquid, yield 86.2%.

[0030] Add 1.31g (8.6mmol) light yellow liquid methyl salicylate and 0.1mol 50% hydrazine hydrate into 30ml absolute ethanol, reflux for 8h, let stand overnight, and precipitate a white solid. Filter and recrystallize with 50% ethanol to obtain 0.98g of salicylhydrazide with a yield of 75.0%. Melting point: 145-147°C.

Embodiment 2

[0031] Example 2: Preparation of 5-(2', 4'-difluorophenyl)-furan-2-carbaldehyde

[0032] Dissolve 12.9g (0.1mol) of 2,4-difluoroaniline in 10ml of water and 25ml of concentrated hydrochloric acid, add 25g of crushed ice, add 25ml of aqueous solution of 6.9g (0.1mol) of sodium nitrite dropwise below 5°C, stir for 10min, then add 9.6 25ml of acetone solution of g (0.1mol) furfural aldehyde and 3.0g of copper chloride were reacted at 25-30°C for 5h. Suction-filtered and dried, and recrystallized with 50% ethanol to obtain 7.46 g of 5-(2',4'-difluorophenyl)-furan-2-carbaldehyde, which appeared as a brown solid, m.p.: 118-119°C, yield 35.9 %.

Embodiment 3

[0033] Example 3: Preparation of N'-5-(2',4'-difluorophenyl)-2-furan-N-(2'-hydroxybenzoyl)hydrazone (I5)

[0034]

[0035] Add 30ml of absolute ethanol to a 50ml three-necked flask equipped with a thermometer, mix 1.04g (0.005mol) of 5-(2',4'-difluorophenyl)-furan-2-carbaldehyde with 0.76g (0.005mol) of water Salicylic hydrazide was added thereto, heated to reflux for 5h. After the reaction solution was cooled, a large amount of solids precipitated out. After filtration, a light yellow solid was obtained. After recrystallization from absolute ethanol, 1.43 g of light yellow needle-shaped crystals were obtained, with a yield of 83.6% and a melting point of 248-249°C.

[0036] 1 H-NMR (DMSO-d 6 ,δ H ppm): 6.98-7.05 (m, 3H, 2ArH+FuH), 7.13 (d, J=3.54Hz, 1H, FuH), 7.27 (td, J=8.45, 2.34Hz, 1H, ArH-Fu), 7.41- 7.48(m, 2H, ArH-Fu+ArH), 7.86-7.93(m, 2H, ArH-Fu+ArH), 8.42(s, 1H, CH=N), 11.80(s, 1H, OH), 11.87( s, 1H, NH). IR (cm -1 ): 3300, 3100, 2700, 1630, 1600, 1530, 1500,...

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Abstract

The invention relates to an N'-5-substitutent aryl-2-furan-N-substitutent benzoyl hydyne compound (I) with a novel structure. The compound is produced by reaction of substituted aryl formohydrazide and 5-substitent aryl furan-2-formaldehyde. The compound is found through research to have anti-tumor activities in which people are interested, particularly the activities for resisting stomach cancer, human liver cancer and nasopharynx cancer.

Description

technical field [0001] The present invention relates to a class of N'-5-substituted aryl-2-furan-N-substituted benzoyl hydrazone compound (I) with novel structure, its preparation method and its application as an anti-tumor growth inhibitor. Background technique [0002] N-substituted aryl acylhydrazone compounds have a variety of physiological activities, and some N-substituted aryl acylhydrazone compounds have been disclosed in, for example, the following (patent) documents: Ferimzone (ferimzone) was developed by Japanese Takeda Pharmaceutical in 1980 Pyrimidine hydrazone fungicides developed by industrial companies (patent number: EP19450, patent application date: 1979-05-15, patent publication date: 1980-11-26, patent owner: Japan Takeda Pharmaceutical Industry Company, patent name: Pyrimidine derivatives and their agricultural uses). It is mainly used to prevent diseases caused by pathogenic bacteria such as Cercosporium oryzae, Helminthrosporium oryzae and Pyrosporium...

Claims

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Application Information

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IPC IPC(8): C07D307/52A61K31/341A61P35/00
Inventor 杨新玲崔紫宁凌云黄娟张莉陈馥衡
Owner CHINA AGRI UNIV
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