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3,5-pyrazole diketone derivatives containing exocyclic double bond structural unit and its preparation method and use

A technology of pyrazolidinedione and pyrazolidinedione, which is applied in the field of pharmaceutical chemical synthesis to achieve the effects of high reaction yield, good market application prospects, and mild reaction conditions

Active Publication Date: 2015-12-09
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no literature report on the anti-tumor effect of this type of compound containing 3,5-pyrazoledione double bond.

Method used

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  • 3,5-pyrazole diketone derivatives containing exocyclic double bond structural unit and its preparation method and use
  • 3,5-pyrazole diketone derivatives containing exocyclic double bond structural unit and its preparation method and use
  • 3,5-pyrazole diketone derivatives containing exocyclic double bond structural unit and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0015] Embodiment 11, the preparation of 2-two p-chlorophenyl-4-p-fluorobenzylidene-3,5-pyrazolidinedione

[0016] Add 2.008g (15.74mmol) p-chloroaniline and 50ml toluene into a 100ml three-neck flask, stir to dissolve, install the reflux tube and drying tube, add 6.892g (79.31mmol) MnO 2 , heated to 90°C, kept the temperature for 15 minutes, then raised the temperature to 118°C, and started to reflux. The TLC plate was spotted every 30 minutes to monitor the reaction progress (petroleum ether: chloroform = 2:1). Stop heating after the reaction is completed, and filter the reaction solution while hot with a sand core funnel covered with silica gel, and wash the filter cake twice with toluene. The filtrate was rotary evaporated to obtain an orange-yellow solid. Continue to wash the filter cake with the toluene evaporated by rotary evaporation, and repeat the operation until the filtrate after washing is colorless. The compound p-chloroazobenzene was obtained.

[0017] Add 0...

Embodiment 21

[0020] Example 21, Preparation of 2-two p-chlorophenyl-4-p-chlorobenzylidene-3,5-pyrazolidinedione

[0021] P-chlorobenzaldehyde was replaced by p-fluorobenzaldehyde, and the preparation method was the same as in Example 1 to obtain a yellow solid compound with a yield of 93.9%, m.p.204-206 ° C; 1 HNMR (400MHz, CDCl 3 )δ8.51(d, J =8.5Hz,2H),8.11(s,1H),7.51(d, J =8.5Hz,2H),7.40(dd, J =9.1,2.2Hz,2H),7.37(dd, J =9.1,2.2Hz,2H),7.31(d, J =8.9Hz,2H),7.31(d, J =8.9Hz,2H). 13 CNMR (101MHz, CDCl 3 )δ163.51, 161.84, 153.06, 141.23, 136.22, 134.87, 134.77, 132.47, 132.20, 130.73, 129.46, 129.26, 129.24, 123.74, 123.26, 116.89.HRMS(ESacIld.forC): m / zc 22 h 13 Cl 3 N 2 o 2 (M+H) + ,443.0121,found,443.0126.

Embodiment 31

[0022] Example 31, Preparation of 2-two-p-chlorophenyl-4-p-bromobenzylidene-3,5-pyrazolidinedione

[0023] Substitute p-bromobenzaldehyde for p-fluorobenzaldehyde, the preparation method is the same as in Example 1, and the yield of yellow solid compound is 94.2%, m.p.191-192°C; 1 HNMR (400MHz, CDCl 3 )δ8.39(d, J =8.6Hz,2H),8.07(s,1H),7.66(d, J =8.6Hz,2H),7.35(dd, J =9.1,2.2Hz,2H),7.35(dd, J=9.1,2.2Hz,2H),7.30(d, J =8.9Hz,2H),7.30(d, J =8.9Hz,2H). 13 CNMR (101MHz, CDCl 3 )δ161.41, 160.65, 152.11, 140.32, 135.13, 133.76, 133.24, 131.34, 131.11, 129.66, 128.44, 128.23, 128.16, 122.65, 122.14, 115.23. HRMS (ESIld.forC): m / zc 22 h 13 Cl 2 N 2 o 2 Br(M+H) + ,486.9616,found,486.9612.

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Abstract

The invention belongs to the technical field of pharmaceutical chemical synthesis, and discloses a 3,5-pyrazoledione double bond compound with an N-substituted p-halogenobenzene ring with antitumor activity, a synthesis method and an application thereof. The compounds of the present invention have the general formula Ⅰ structure Ⅰ Middle: X is F, Cl, Br respectively; R1 is p-fluorophenyl, p-chlorophenyl, p-bromophenyl, 3-methoxy-4-hydroxyphenyl, 2,3-di-p-methoxybenzene 3,4-difluorophenyl, phenylpropenyl, 2-furylpropenyl. The anti-tumor activity experiment in vitro proves that the compounds have obvious inhibitory and killing effects on various tumor cells, and can be used to prepare drugs for treating tumor diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemical synthesis, and relates to 3,5-pyrazoledione derivatives, in particular to 3,5-pyrazoledione double bond compounds with anti-tumor activity and N-substituted p-halogen benzene rings, and their synthesis methods and its uses. Background technique [0002] 3,5-Pyrazole diketones belong to a kind of non-steroidal anti-inflammatory drugs, and its main representative drugs are phenylbutazone and hydroxybuzone. It has good anti-inflammatory and analgesic effects, and is used to treat rheumatoid arthritis and rheumatoid arthritis. 3,5-Pyrazoledione NSAIDs are non-selective COX-2 inhibitors. In recent years, with the in-depth study of molecular pharmacology, it has been found that COX-2 is closely related to the occurrence, development and metastasis of various human tumor cells. COX-2 inhibitors can be used as anti-tumor drugs; or combined with anti-tumor drugs Medication is used to improve the curati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/36C07D231/34C07D405/06A61K31/4152A61K31/4155A61P35/00
CPCC07D231/34C07D231/36C07D405/06
Inventor 刘宏民张秋荣陈婷顾一飞李岩琦章旭耀吴朝阳薛登启贺鹏邵坤鹏陈鹏举
Owner ZHENGZHOU UNIV
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