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3,5-pyrazoldione derivative containing exocyclic double bond structure unit and preparation method and application thereof

A technology of pyrazole diketone and medicine, which is applied in the field of medicinal chemical synthesis, and achieves the effects of mild reaction conditions, high reaction yield and simple operation

Active Publication Date: 2014-02-26
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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-pyrazoldione derivative containing exocyclic double bond structure unit and preparation method and application thereof
  • 3,5-pyrazoldione derivative containing exocyclic double bond structure unit and preparation method and application thereof
  • 3,5-pyrazoldione derivative containing exocyclic double bond structure unit and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1 Preparation of 1,2-di-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 (developing agent 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.

[00...

Embodiment 2

[0020] Example 2 Preparation of 1,2-di-p-chlorophenyl-4-p-chlorobenzylidene-3,5-pyrazolidinedione

[0021] Substitute p-chlorobenzaldehyde for p-fluorobenzaldehyde, and the preparation method is the same as in Example 1 to obtain a yellow solid compound with a yield of 93.9%, m.p. 204-206°C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.51 (d, J = 8.5 Hz, 2H), 8.11 (s, 1H), 7.51 (d, J = 8.5 Hz, 2H), 7.40 (dd, J = 9.1, 2.2 Hz, 2H), 7.37 (dd, J = 9.1, 2.2 Hz, 2H), 7.31 (d, J = 8.9 Hz, 2H), 7.31(d, J = 8.9 Hz, 2H) . 13 C NMR (101 MHz, CDCl 3 ) Δ 163.51, 161.84, 153.06, 141.23, 136.22, 134.87, 134.77, 132.47, 132.20, 130.73, 129.46, 129.24, 123.74, 116.89. HRMS (ESI): m / z cack. 22 h 13 Cl 3 N 2 o 2 (M+H) + , 443.0121,found, 443.0126.

Embodiment 3

[0022] Example 3 Preparation of 1,2-di-p-chlorophenyl-4-p-bromobenzylidene-3,5-pyrazolidinedione

[0023]P-bromobenzaldehyde was substituted for p-fluorobenzaldehyde, and the preparation method was the same as in Example 1 to obtain a yellow solid compound with a yield of 94.2%, m.p. 191-192°C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.39 (d, J = 8.6 Hz, 2H), 8.07 (s, 1H), 7.66 (d, J = 8.6 Hz, 2H), 7.35 (dd, J = 9.1, 2.2 Hz, 2H), 7.35 (dd, J = 9.1, 2.2 Hz, 2H), 7.30 (d, J = 8.9 Hz, 2H), 7.30(d, J = 8.9 Hz, 2H). 13 C NMR (101 MHz, CDCl 3 ) Δ 161.41, 160.65, 152.11, 140.32, 135.13, 133.76, 133.24, 131.34, 131.11, 129.66, 128.44, 128.16, 122.65, 122.23. HRMS (ESI): m / z CACLD. for C 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 chemical synthesis of medicines, and discloses a 3,5-pyrazoldione double bond compound of an N-substituted p-halobenzene ring with anti-tumor activity, and a synthesis method and application thereof. The compound disclosed by the invention has the structure shown by the general formula I; in the general formula I, X refers to F, Cl and Br respectively, and R1 refers to p-fluorophenyl, p-chlorphenyl, p-bromophenyl, 3-methoxy-4-hydroxyphenyl, 2,3-bis(p-methoxyphenyl), 3,4-difluorophenyl, phenylpropenyl and 2-furanpropenyl. In-vitro anti-tumor activity experiments prove that the compound has obvious effects on inhibiting and killing multiple tumor cells and can be used for preparing medicines 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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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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