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Aryl hydrazide compounds with antineoplastic activity

A compound, aryl technology, applied in the application field of anti-tumor growth inhibitor, can solve the problem of unmentioned anti-tumor activity and the like

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

[0004] These compounds are reported to have highly effective insect growth regulator activity, but no antitumor activity is mentioned

Method used

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  • Aryl hydrazide compounds with antineoplastic activity
  • Aryl hydrazide compounds with antineoplastic activity
  • Aryl hydrazide compounds with antineoplastic activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of p-chlorobenzoyl chloride

[0034]

[0035] Add 1.57g (0.01mol) of p-chlorobenzoic acid and 20ml of toluene into a 50ml three-necked flask, and add 3.57g (0.03mol) of thionyl chloride under stirring. Heating to reflux for 5 hours, distilling off the toluene and the remaining thionyl chloride, and then performing vacuum distillation to collect the fraction at 64~67°C / 0.67kPa to obtain 1.28g of colorless liquid with a yield of 73.6%.

Embodiment 2

[0036] Example 2: Preparation of N-tert-butyl-5-(4'-chloro-phenyl)furan-2-formylhydrazide

[0037]

[0038] Add 2g (0.016mol) of tert-butylhydrazine hydrochloride and 10ml of dichloromethane into a 50ml three-necked flask equipped with a thermometer, stir and cool to 0°C, add dropwise 6.4g (0.016mol) of 10% aqueous sodium hydroxide solution, Control the rate of addition to keep the temperature around 0°C. After the dropwise addition was completed, stir for 30 min. A solution of 0.96 g (0.004 mol) of p-chlorophenylfuroyl chloride in 10 ml of dichloromethane and 1.6 g (0.004 mol) of 10% aqueous sodium hydroxide solution were added dropwise at 0°C. Control the rate of addition so that both are added at the same time. After the dropwise addition, slowly rise to room temperature and react at 25°C for 5.5-6h. After filtering, the organic layer was washed with water and dried overnight with magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off ...

Embodiment 3

[0039] Example 3: Preparation of N-tert-butyl-N'-(4'-chlorobenzoyl)-5-(4'-chlorophenyl)furan-2-formylhydrazide (I2)

[0040]

[0041] Add 1.46g (0.005mol) of N'-tert-butyl-5-(4'-chloro-phenyl)furan-2-carboxylhydrazide and 10ml of anhydrous toluene to a 50ml three-necked flask equipped with a thermometer. The temperature was lowered to 0°C, and at the same time, a solution of 0.875g (0.005mol) p-chlorobenzoyl chloride in 10ml of toluene and 0.5g of 40% NaOH aqueous solution were added dropwise, and the temperature was controlled at 0-5°C. After dripping, it was slowly raised to room temperature and reacted for 2h. Filtration gave a white solid, which was washed with ether-methanol (V乙醚 / V 甲醇 =1 / 1) to obtain 1.86 g of white needle-like crystals with a yield of 86.3% and a melting point of 221.5-223.5°C.

[0042] 1 H-NMR (DMSO-d 6 ,δ H ppm): 1.50(s, 9H, t-Bu), 7.11~7.12(d, 1H, FuH), 7.15~7.16(d, 1H, FuH), 7.36~7.39(d, 2H, ArH), 7.49~7.52 (d, 2H, ArH), 7.55-7.57 (d, 2H, A...

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PUM

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Abstract

The invention relates to novel N-tert-butyl-N-substituted aroyl group-N'-(5-substituted aryl-2-furanylcarbonyl) hydrazine compounds, which have a general formula (I), wherein Ar1 and Ar2 are as defined in an instruction; and the invention also relates to a preparation method thereof and application of the compounds used as an antitumor depressor.

Description

technical field [0001] The present invention relates to a novel N-tert-butyl-N-substituted aroyl-N'-(5-substituted aryl-2-furyl)hydrazine compound, its preparation and its application as an anti-tumor growth inhibitor. Background technique [0002] N-substituted aryl hydrazides have good biological activity, and some N-substituted aryl hydrazides have been disclosed in, for example, the following (patent) documents: In 1988, Rohm & Haas (Rohm&Haas) company in the United States developed Hydrazine (RH-5849) (Aller, H.E.; Ramsay, J.R. RH-5849-a novelinsect growth regulator with a new mode of action. Brighton Crop Protection Conference--Pests and Diseases (1988), (2), 511-18. ); in the 1990s, Japan's Nippon Kayaku Co.Ltd and Sankyo Co.Ltd jointly developed chromafenozide ANS-118 (chromafenozide) (JP 6-172342, 1994; JP 8-231529, 1996); Southern my country Jiangsu Base of Pesticide Innovation Center synthesized and screened a new compound JS-118 with high activity (Zhang Xiangning,...

Claims

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Application Information

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IPC IPC(8): C07D409/12C07D307/68A61K31/341A61P35/00
Inventor 杨新玲崔紫宁凌云黄娟张莉陈馥衡
Owner CHINA AGRI UNIV
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