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Chiral bisferrocene acylthiourea compound as well as synthesis method and application of compound

A technology of bisferrocenylthiourea and ferrocenylthiourea, applied in the preparation of anticancer drugs, in the field of chiral bisferrocenylthiourea compounds, can solve the problem of bis(acylthiourea) The problem of fewer compounds, etc., achieves the effect of simple synthesis method and easy separation and purification

Inactive Publication Date: 2013-03-13
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, people have tried to synthesize monoacylthiourea compounds with various structures, but there are still few reports on bis(acylthiourea) compounds, and there are few reports on the synthesis of chiral acylthiourea compounds.

Method used

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  • Chiral bisferrocene acylthiourea compound as well as synthesis method and application of compound
  • Chiral bisferrocene acylthiourea compound as well as synthesis method and application of compound
  • Chiral bisferrocene acylthiourea compound as well as synthesis method and application of compound

Examples

Experimental program
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Embodiment 1

[0020] Example 1 Preparation of chiral bisferrocenylthiourea compound of the present invention

[0021] (1) In a three-neck round bottom flask equipped with a condenser and a stirrer, add 4.08g (17.7mmol) of ferrocenecarboxylic acid and 70ml of anhydrous benzene and stir to obtain a yellow suspension. Add 2.83g (1.8 ml, 20.6 mmol) phosphorus trichloride, and then the reaction mixture was stirred under heating in a water bath at 55-60°C. The ferrocenecarboxylic acid was gradually dissolved, and the solution turned from yellow to dark red, and the reaction lasted for 3 hours. After cooling, the reaction mixture was poured into a distillation flask, the solvent was removed under reduced pressure, and the residue was extracted with 60ml of petroleum ether after cooling. The solvent was removed from the extract under reduced pressure, and cooled to obtain 4.13 g of ferrocenecarbonyl chloride.

[0022] (2) Dissolve 4.13g (16.6mmol) of ferrocenecarbonyl chloride in 30ml of anhydrou...

Embodiment 2

[0028] Example 2 Anticancer activity experiment of chiral bisferrocenylthiourea compound of the present invention

[0029] 1) Cell model: liver cancer cell (HepG2) was used as the model.

[0030] 2) Detection method: MTT colorimetric method to detect anticancer activity test:

[0031] Taking liver cancer cells (HepG2) as a model, the effect of the chiral bisferrocenylthiourea compound (Q=H in the general structural formula) of the present invention on its biological activity was studied. Take the HepG2 cell suspension (7.5×10 3 cells / mL) were inoculated in 96-well cell culture plate, 200 μL per well, placed at 37C, 5% CO 2 Incubate in the incubator for 16 hours. After the cells are completely adhered to the wall, add different concentrations of ligands (1.0 μM and 0.1 mM) and incubate for 24, 48 and 72 hours. Use untreated blank cells as the control, and set 6 wells for each group of experiments. Repeat hole. After the reaction, add 20 μL MTT (5 mg / mL) to each well, contin...

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Abstract

The invention provides an acylthiourea compound and particularly relates to a chiral bisferrocene acylthiourea compound (1R, 2R)-1,2-bis(ferrocene acylthiourea) cyclohexane as well as a synthesis method and an application of the compound. According to the invention, ferrocenecarboxylic acid is adopted as a raw material, then active groups of ferrocenyl and acylthiourea are gathered through three steps of reaction, and then the chiral target is synthesized. The synthesis method disclosed by the invention is simple and convenient; the product is easy to separate and purify, and the yield can reach 60-70%; and the synthesis method is suitable for industrial popularization and application. The compound has potential application values in the aspect of construction of medicines and bioactive compounds and can be applied to preparation of anti-cancer medicaments.

Description

technical field [0001] The present invention relates to acylthiourea compounds, specifically a chiral bisferrocenylthiourea compound, i.e. (1R,2R)-1,2-bis(ferrocenylthioureido)cyclohexane and its Synthetic method, and the application of the compound in the preparation of anticancer drugs. Background technique [0002] In the 1960s, Schroepl first synthesized the first aroylthiourea and found that such compounds had good insecticidal activity (E.Schroepl, et al., Pharmazie, 23, 1968, 484), and then people successively synthesized A large number of aroylthiourea compounds have been found to have a wide range of biological activities through biological activity tests, and can be used as insecticides, herbicides, fungicides, anti-viruses, plant growth regulators, anti-tumors, local anesthetics and analgesics. Active ingredients have always been one of the research hotspots in the fields of drug creation and chemical development. The Chinese invention patent with the authorizat...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61P35/00
Inventor 段新娥李英奇童红波刘滇生
Owner SHANXI UNIV
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