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3-hydroxyl cholest-6-keto aromatic aldehyde azine steroidal compound, synthetic method of steroidal compound and application of steroidal compound in preparation of anti-tumour drug

A kind of aromatic aldehyde azine steroid and aromatic aldehyde azine technology, which is applied to 3-hydroxycholest-6-one aromatic aldehyde azine steroid compound and its synthesis and application field in the preparation of antitumor drugs, which can solve the problem of The application has not seen reports and other issues

Inactive Publication Date: 2013-09-04
GUANGXI TEACHERS EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no report about the 3β-hydroxycholest-6-one aromatic aldehyde azine steroid compound, its synthesis method, and its application in the preparation of antitumor drugs

Method used

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  • 3-hydroxyl cholest-6-keto aromatic aldehyde azine steroidal compound, synthetic method of steroidal compound and application of steroidal compound in preparation of anti-tumour drug
  • 3-hydroxyl cholest-6-keto aromatic aldehyde azine steroidal compound, synthetic method of steroidal compound and application of steroidal compound in preparation of anti-tumour drug
  • 3-hydroxyl cholest-6-keto aromatic aldehyde azine steroidal compound, synthetic method of steroidal compound and application of steroidal compound in preparation of anti-tumour drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Preparation of 3-hydroxycholesteryl-6-ketoneacetone azine (1)

[0024] Step 1: Preparation of cholest-4-ene-3,6-dione

[0025] Weigh 4g of cholesterol and place it in a 250mL reaction flask, add 100mL of dichloromethane to dissolve the cholesterol completely, then add 10g of PCC, the solution turns black rapidly. Stir the reaction at 35°C for 48h, and stop the reaction after tracking the reaction to the point of no raw material by TLC. The reactant was poured into a short column of silica gel, rinsed with ethyl acetate, the collected solution was evaporated under reduced pressure to remove the solvent, and separated by column chromatography to obtain 3.2 g of a light yellow solid product with a yield of 77%; m.p.131-132°C. The structure of the product was confirmed by IR, NMR and MS analysis.

[0026] Step 2: Preparation of 3β-hydroxycholestan-6-one

[0027] Weigh 200 mg of cholest-4-ene-3,6-dione and 120 mg of nickel chloride hexahydrate, put them in a 100...

Embodiment 2

[0032] Example 2 Preparation of 3-hydroxycholest-6-ketone benzaldehyde azine (2)

[0033] Weigh 60mg of 3-hydroxy-cholester-6-one hydrazone and place it in a 100mL round bottom flask, add 15mL of absolute ethanol to dissolve it completely, add 16mg of benzaldehyde, heat up to 60°C and stir for 3 hours, TLC tracking, raw material point The reaction was terminated after the disappearance, and 55 mg of light yellow crystals were obtained by plate chromatography after vacuum distillation. Yield: 75%, m.p.65-67°C. The structure of the product was confirmed by IR, NMR and MS analysis.

Embodiment 3

[0034] Example 3 Preparation of 3-hydroxycholest-6-one-3-pyridinecarbaldehyde azine (3)

[0035] Weigh 60mg of 3-hydroxy-cholester-6-one hydrazone and place it in a 100mL round bottom flask, add 15mL of absolute ethanol to dissolve it completely, add 17mg of 3-pyridinecarbaldehyde, heat up to 60C° and stir for 3 hours, TLC tracking, raw materials The reaction was terminated after the dots basically disappeared, and 51 mg of brown-red crystals were obtained by plate chromatography after vacuum distillation, yield: 71%, m.p.110-112°C. The structure of the product was confirmed by IR, NMR and MS analysis.

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Abstract

The invention relates to a 3-hydroxyl cholest-6-keto aromatic aldehyde azine steroidal compound with an azine structure. The structural formula of the steroidal compound is described in the specification. 3-hydroxyl cholest-6-keto acetone acetone azine (1), 3-hydroxyl cholest-6-keto benzaldehyde azine (2), 3-hydroxyl cholest-6-keto-3-pyridine methanol azine (3), 3-hydroxyl cholest-6-keto-3-thiophene methanol azine (4), 3-hydroxyl cholest-6-keto-3-hydroxy benzaldehyde azine (5), 3-hydroxyl cholest-6-keto-2-naphthaldehyde azine (6), 3-hydroxyl cholest-6-keto-4-quinolinecarboxaldehyde azine (7), and 3-hydroxyl cholest-6-keto-6-methoxy naphthaldehyde azine (8) are shown in the specification. Experiments prove that the 3-hydroxyl cholest-6-keto aromatic aldehyde azine steroidal compound has an obvious inhibiting effect on multiple tumour cell strains and can be applied to preparation of a drug used for treating cancer.

Description

1. Technical field [0001] The invention relates to a class of 3-hydroxycholest-6-one aromatic aldehyde azine steroid compound, its synthesis method, and its application in the preparation of antitumor drugs. 2. Background technology [0002] Azine and its derivatives are an important class of compounds. It has been reported in the literature that azine compounds are widely used in the fields of biomedicine and pesticides, and they have extensive research value in the development of antibacterial, insecticidal and antitumor drugs. In the research on the synthesis of azine compounds, Chinese patent CN200580028484.X once reported a class of azine-carboxamide compounds used as anticancer drugs. Meanwhile, in the synthesis of steroidal azine compounds, a class of 6-carbonylcholestane thiazolidinone azine compounds (Salman Ahmad Khan, Abdullah M. Asiria, Mohammed Yusuf. Synthesis and biological evaluation of some thiazolidinone derivatives has been reported) of steroid as antiba...

Claims

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Application Information

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IPC IPC(8): C07J41/00C07J43/00A61K31/575A61K31/58A61P35/00
Inventor 崔建国刘亮黄燕敏甘春芳黄珊林启福
Owner GUANGXI TEACHERS EDUCATION UNIV
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