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Preparation method of 6-oxo-7-oxa-b-homo-cholesta-3-thionylhydrazone compound and its application in antitumor drugs

A technology of -b-homo- and thionylhydrazone, applied in antineoplastic drugs, steroids, drug combinations, etc.

Inactive Publication Date: 2011-12-21
GUANGXI TEACHERS EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there are few reports on the inhibitory effect of these compounds on mammalian cells

Method used

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  • Preparation method of 6-oxo-7-oxa-b-homo-cholesta-3-thionylhydrazone compound and its application in antitumor drugs
  • Preparation method of 6-oxo-7-oxa-b-homo-cholesta-3-thionylhydrazone compound and its application in antitumor drugs
  • Preparation method of 6-oxo-7-oxa-b-homo-cholesta-3-thionylhydrazone compound and its application in antitumor drugs

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Experimental program
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Embodiment 1

[0016] Preparation of 6-oxo-7-oxa-B-Homo-cholesta-3-thionylhydrazone (6)

[0017] Step 1: Preparation of intermediate product (2)

[0018] Add 2.000g (4.09mmol) of cholesterol to the 100mL reaction bottle, and use 80mL CH 2 Cl 2 After dissolving, 5.550 g of pyridinium chlorochromate (PCC) was added at one time, the solution turned black rapidly, and the reaction was carried out with stirring at room temperature. TLC monitoring (ethyl acetate:petroleum ether=1:4), there was no raw material point after 28 hours of reaction, and the reaction was stopped. The reactant was poured into a short column of silica gel, eluted with ethyl acetate, the solvent was distilled off under reduced pressure, and the crude product was separated by 200-300 mesh silica gel column chromatography (eluent: ethyl acetate:petroleum ether=1:6), 1.839 g of yellowish solid 2 was obtained with a yield of 89%. The structure of the product was confirmed by IR, NMR and MS analysis.

[0019] Step 2: Prepara...

Embodiment 2

[0028] This example uses the 6-oxo-7-oxa-B-Homo-cholesta-3--thionylhydrazone compound of the present invention to test the activity of inhibiting tumor cell growth and proliferation on certain tumor cells Test Results.

[0029] Select 6-oxo-7-oxa-B-Homo-cholesta-3--thionylhydrazone compound test of the present invention to human liver cancer cell line (7404), cervical cancer cell line (HeLa), gastric cancer Cytotoxicity of cell line (7901), gastric cancer cell line (MGC-803), lung cancer cell line (SPC-A), and liver cancer cell line (HEPG-2). In vitro cytotoxicity assays were performed using the MTT method. Add different concentrations of 6-oxo-7-oxa-B-Homo-cholesta-3-thionylhydrazone compound to the logarithmic growth phase cells cultured in the 96-well plate, and carry out 3 parallel experiments simultaneously, compared with the control group. After cultivating for 72 hours, add MTT, measure its absorbance, and calculate the concentration of the compound when inhibiting t...

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Abstract

A 6-oxo-7-oxa-B-Homo-cholesta-3-thionylhydrazone compound has the following chemical structural formula: the 6-oxo-7-oxa-B-Homo- Cholesta-3-thionylhydrazone compound is formed from cholesterol through the chemical method of PCC oxidation, NaBH4 reduction, Bayer-Villiger oxidation, Corrin oxidation and addition. Experiments have proved that the 6-oxo-7-oxa-B-Homo-cholesta-3-thionylhydrazone compound of the present invention has obvious inhibitory effect on various tumor cell lines, and can be used as in the application.

Description

1. Technical field [0001] The invention relates to a preparation method of 6-oxo-7-oxa-B-Homo-cholesta-3-thionylhydrazone compound and its application in the preparation of antitumor drugs. 2. Background technology [0002] Cancer is a malignant tumor and one of the most harmful diseases to human health and quality of life. Finding anti-tumor drugs with high efficiency, high selectivity and less side effects is the main direction of drug research and development. [0003] B-ring steroid compounds such as brassinosteroids have the physiological functions of auxin and cytokinin, and also have other unique physiological functions. They can show strong physiological activities at extremely low concentrations. The low level is unmatched by other types of plant hormones. But so far, there are few reports on the inhibitory effect of these compounds on mammalian cells. Jana (M Jana, S Jana, K et al.J.Phytochemistry, 2008, 69: 418-426.) studied the anticancer effect of natural b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61K31/585A61P35/00
Inventor 崔建国甘春芳黄燕敏
Owner GUANGXI TEACHERS EDUCATION UNIV
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