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N-substituted piperazine bismuth dicarbamate (Ⅲ) complex and its preparation method and application in the preparation of antitumor drugs

An anti-tumor drug, the technology of bismuth dicarbaminate, which is applied in the field of anti-tumor drugs, can solve the problems of single structure, low clinical application value, and few anti-tumor cell lines, and achieve wide application prospects, good anti-tumor activity, and significant inhibitory effect. The effect of tumor activity

Inactive Publication Date: 2016-06-08
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are problems of single structure, few anti-tumor cell lines, and low clinical application value, and there is still a long way to go before clinical application

Method used

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  • N-substituted piperazine bismuth dicarbamate (Ⅲ) complex and its preparation method and application in the preparation of antitumor drugs
  • N-substituted piperazine bismuth dicarbamate (Ⅲ) complex and its preparation method and application in the preparation of antitumor drugs
  • N-substituted piperazine bismuth dicarbamate (Ⅲ) complex and its preparation method and application in the preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: 1-methylpiperazine bismuth dicarbamate and its preparation

[0027] Add 0.501g (5mmol) 1-methylpiperazine, 0.25g (6mmol) sodium hydroxide, and 15mL anhydrous methanol to a round-bottomed flask, stir and dissolve in a cold water bath at 0-5°C, then add dropwise 0.76g ( 10mmol) CS 2 , Low temperature magnetic stirring reaction for 2h, magnetic stirring reaction at room temperature for 4h.

[0028] 0.53g (1.7mmol) BiCl 3 Dissolve in 15 mL of anhydrous methanol, drop into the above reaction solution, stir at room temperature for 3 h, filter with suction, wash with anhydrous methanol, and dry in vacuo. The solid was recrystallized from dichloromethane and ethanol to obtain 0.85 g of a yellow powder solid, yield 69.4%, melting point: 197-199°C, number N058.

[0029] 1 HNMR (400MHz, CDCl 3 ),δ:2.326(9H,s,-CH 3 ),2.505~2.530(12H,t,N-CH 2 , J=4.8Hz), 4.131~4.155(12H,t,N-CH 2 ,J=4.8Hz).

[0030] Molecular formula: C 18 h 33 N 6 S 6 Bi, elemental analysis r...

Embodiment 2

[0031] Embodiment two: 1-ethylpiperazine bismuth dicarbamate and its preparation

[0032] Add 0.571g (5mmol) 1-ethylpiperazine, 0.25g (6mmol) sodium hydroxide, and 15mL anhydrous methanol to a round-bottomed flask, stir and dissolve in a cold water bath at 0-5°C, then add dropwise 0.76g ( 10mmol) CS 2 , Low temperature magnetic stirring reaction for 2h, magnetic stirring reaction at room temperature for 4h.

[0033] 0.53g (1.7mmol) BiCl 3 Dissolve in 15mL of anhydrous methanol, drop into the above reaction solution, and stir at room temperature for 4h. A yellow precipitate precipitated, was suction filtered, washed with anhydrous methanol, and dried. The solid was recrystallized from acetonitrile to obtain 1.15 g of a yellow solid with a yield of 88.8%. Melting point: 122-124°C, number N063.

[0034] 1 HNMR (400MHz, CDCl 3 ),δ:1.094~1.129(9H,t,-CH 3 , J=6.8Hz), 2.430~2.482(6H,q,-CH 2 ,J=6.8Hz),2.539~2.563(12H,t,N-CH 2 , J=4.8Hz), 4.135~4.159(12H,t,N-CH 2 ,J=4.8Hz). ...

Embodiment 3

[0036] Example three: 1-benzylpiperazine bismuth dicarbamate and its preparation

[0037] Add 0.881g (5mmol) 1-benzylpiperazine, 0.25g (6mmol) sodium hydroxide, and 15mL anhydrous methanol to a round-bottomed flask, stir and dissolve in a cold water bath at 0-5°C, then add dropwise 0.76g ( 10mmol) CS 2 , Low temperature magnetic stirring reaction for 2h, magnetic stirring reaction at room temperature for 4h.

[0038] 0.53g (1.7mmol) BiCl 3 Dissolve in 15 mL of anhydrous methanol, drop into the above reaction solution, stir at room temperature for 4 h, filter with suction, wash with anhydrous methanol, and dry in vacuo. The solid was recrystallized from dichloromethane-methanol to obtain 1.29 g of yellow crystals, yield 80.4%, melting point: 255-256°C.

[0039] 1 HNMR (400MHz, CDCl 3 ),δ:2.530~2.554(12H,t,N-CH 2 , J=4.8Hz), 3.529(6H,s,Ph-CH 2 ),4.098~4.122(12H,t,N-CH 2 , J=4.8Hz), 7.269~7.349 (15H, m, Ph-H, J=6.4-7.6Hz).

[0040] Molecular formula: C 36 h 45 N 6 S ...

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Abstract

The invention relates to an N-substituted piperazine bismuth dithiocarbamate (III) complex. The complex has the following structural formula as shown in the specification, wherein R is methyl, ethyl, benzyl, acetyl or 2-pyridyl. The N-substituted piperazine bismuth dithiocarbamate (III) complex has good tumor activity resistance, has significant tumor inhibiting activity on gastric cancer, lung cancer, liver cancer, colorectal cancer, cervical cancer, ovarian cancer, breast cancer, leukemia, colon cancer and the like, and has a wide application prospect when being developed into novel anti-tumor medicaments.

Description

technical field [0001] The invention relates to the technical field of antineoplastic drugs, in particular to N-substituted piperazine bismuth (III) complexes and their preparation methods and their application in the preparation of antineoplastic drugs. Background technique [0002] Malignant tumors (cancer) are a serious threat to human health and life. Every year, patients who die from cancer account for about a quarter of the total death toll, and the incidence rate is increasing year by year. Cancer prevention and treatment has become a major issue for medical and life science workers. one of the research topics. The incidence of cancer in my country is astonishing and has become the second most cancer-incidence country in the world. Statistical data (WHOGLOBOCAN2008) shows that all new cancer cases in China are 2.8 million, which is twice the number of new cancer cases in the United States (1.4 million in the United States); In the same year, the number of cancer death...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/21C07D213/75A61K31/495A61K31/496A61P35/00A61P35/02
CPCC07D213/74C07D295/21
Inventor 郭应臣张健卓立宏邱东方柳文敏郭婷
Owner NANYANG NORMAL UNIV