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Substituted thiazolidinedicarbamate bismuth complexes and uses thereof

A technology of thiazolidine ammonia and complexes, which is applied in the field of anticancer drug research, can solve the problems of few antitumor cell strains, low compound stability, and low clinical application value, and achieve good uptake rate, strong anticancer activity, and good Effect of antitumor activity

Active Publication Date: 2016-04-06
HENAN QUANYU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] R and R in the structural formula 1 The same or different, each is alkyl or alkyl substituted, aryl or aryl substituted, X is halide or pseudohalide, n is 2 or 3, as an antitumor agent, although this compound can reduce to a certain extent The survival coefficient of tumor cells, but the compound has the following disadvantages: ①Although it is mentioned in the article that "the compound can act on animal or human tumors, tumors include but are not limited to breast cancer, ovarian cancer, melanoma, kidney cancer and non-small cell lung cancer", but there are few anti-tumor cell strains for a specific compound; ②The stability of the compound is small, and R and R 1 It is substituted by alkyl or aryl, so that its molecular extension is longer and its molecular structure is larger, which inhibits the activity of the molecule to a certain extent, which is not conducive to the anticancer activity in the clinical application process, and its clinical application value is low

Method used

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  • Substituted thiazolidinedicarbamate bismuth complexes and uses thereof
  • Substituted thiazolidinedicarbamate bismuth complexes and uses thereof
  • Substituted thiazolidinedicarbamate bismuth complexes and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of bismuth thiazolidinedicarbamate (A)

[0041] Add 0.445g (5mmol) tetrahydrothiazole, 0.25g (6mmol) sodium hydroxide, and 15mL anhydrous methanol to a 50mL round bottom flask, stir and dissolve in a cold water bath at 0~5°C, then add 0.76g (10mmol) dropwise CS 2 , Low temperature magnetic stirring reaction for 2h, magnetic stirring reaction at room temperature for 4h.

[0042] 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 with dichloromethane and ethanol to obtain 0.94g of yellow powder solid, yield 80.3%, melting point: 137~138°C (carbonized to black).

[0043] Structural Characterization: Proton Magnetic Resonance (NMR) 1 HNMR), record the relevant signals of atoms under resonance as follows:

[0044] 1 HNMR (CDCl 3 ,400MHz),δ:3.184-3.215(6H,t,S-CH 2 ,J=6.4Hz),

...

Embodiment 2

[0048] Preparation of 2-methylthiazolidinedicarbamate bismuth (B)

[0049] Add 0.516g (5mmol) 2-methylthiazolidine, 0.25g (6mmol) sodium hydroxide, and 15mL anhydrous methanol to a 50mL round bottom flask, stir and dissolve in a cold water bath at 0~5°C, then add 0.76g dropwise (10mmol) CS 2 , Low temperature magnetic stirring reaction for 2h, magnetic stirring reaction at room temperature for 4h.

[0050] 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 92.7% and a melting point of 139-140°C (carbonized to black).

[0051] Structural Characterization: Proton Magnetic Resonance (NMR) 1 HNMR), record the relevant signals of atoms under resonance as follows:

[0052] 1 HNMR (CDCl 3 ,400MH...

Embodiment 3

[0056] Preparation of 2-carboxythiazolidinedicarbamate (C)

[0057] Add 0.666g (5mmol) 2-thiazolidine formic acid, 0.40g (10mmol) sodium hydroxide, and 15mL anhydrous methanol into a 50mL round bottom flask, stir and dissolve in a cold water bath at 0~5°C, then add dropwise 0.76g ( 10 mmol) CS 2 , Low temperature magnetic stirring reaction for 2h, magnetic stirring reaction at room temperature for 4h.

[0058] 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. Use 1:1 hydrochloric acid solution to adjust the pH value to 5-6, filter with suction, wash with deionized water, and dry in vacuum. 1.09 g of yellow solid was obtained, the yield was 78.4%, and the melting point was 136-138°C (carbonization decomposition).

[0059] Structural Characterization: Proton Magnetic Resonance (NMR) 1 HNMR), record the relevant signals of atoms under resonance as follows:

[0060] 1 HNMR (DMOS-d 6 ,4...

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Abstract

The invention discloses a substituted bismuth thiazolylalkyldithiocarbamate complex and application thereof. Six structural names of the complex are respectively bismuth thiazolylalkyldithiocarbamate, bismuth 2-methylthiazolylalkyldithiocarbamate, bismuth 2-carboxylthiazolylalkyldithiocarbamate, bismuth 2-ethoxycarbonylthiazolylalkyldithiocarbamate, bismuth S-4-carboxylthiazolylalkyldithiocarbamate and bismuth 4-ethoxycarbonylthiazolylalkyldithiocarbamate. The complex can be used for treating in-vivo diseases or symptoms of individuals, wherein the diseases or symptoms can be cancers, including human colon cancer, human mammary cancer, human myeloma, human liver cancer, human lung cancer, human leukaemia and the like. The complex has the advantages of high purity, favorable antitumor effect and broad acting strain spectrum, increases the varieties of the antineoplastic drugs, and has broad market prospects.

Description

technical field [0001] The invention belongs to the field of anticancer drug research, and in particular relates to a bismuth substituted thiazolidinylcarbamate complex and its application. Background technique [0002] Malignant tumors (cancer) are a serious threat to human health. The number of patients who die from cancer accounts for about a quarter of the total number of deaths each year, and the incidence rate is gradually increasing. The prevention and treatment of cancer has become the main research topic of medical and life science workers. one of the subjects. 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 deaths in China was 1.96 million, while that in the Un...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/04C07D277/06A61K31/555A61P35/00A61P35/02A61P35/04
CPCC07D277/04C07D277/06
Inventor 郭应臣李健孙汝中王峰
Owner HENAN QUANYU PHARMA CO LTD
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