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A class of chromone compounds, their preparation method and their application in the preparation of anti-tumor and enzyme inhibitor drugs

A technology of anti-tumor drugs and compounds, applied in anti-tumor drugs, drug combinations, organic chemistry, etc., can solve the problems of less research and achieve good application prospects

Active Publication Date: 2016-01-20
SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sulfur-containing chromones are rare and less studied

Method used

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  • A class of chromone compounds, their preparation method and their application in the preparation of anti-tumor and enzyme inhibitor drugs
  • A class of chromone compounds, their preparation method and their application in the preparation of anti-tumor and enzyme inhibitor drugs
  • A class of chromone compounds, their preparation method and their application in the preparation of anti-tumor and enzyme inhibitor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: Preparation of sulfur-containing chromone compound oxalicumoneA and compound 1-3

[0050] Preparation method of PDB medium per liter: Mix 200 grams of potatoes, 20 grams of glucose, and 30 grams of sea salt, and dilute to 1L with water. PDB medium was filled into about 300 1000mL Erlenmeyer flasks, each bottle was about 300mL, sterilized by high-pressure steam at 121°C for 25 minutes, and set aside.

[0051] PDA medium configuration method per liter: Mix 200 grams of potatoes, 20 grams of glucose, 30 grams of sea salt, and 20 grams of agar, and dilute to 1L with water. Autoclave at 121°C for 25 minutes and set aside.

[0052] Use a bamboo stick to pick an appropriate amount of Penicillium oxalicum (Penicillium oxalicum) SCSGAF0023CCTCCNO: M2012507 and inoculate it on the PDA medium, and culture it at 28°C for 3 days to obtain a plate with cultured bacteria, and then use a bamboo stick to pick an appropriate amount of bacteria from the plate Inoculate int...

Embodiment 2

[0070] Embodiment 2: Preparation of sulfur-containing chromone compounds 4-8

[0071] Weigh 2.0 mgoxalicumone A and dissolve it in a 5 mL flask containing 0.5 mL of anhydrous pyridine, add 15 μl of 3,5-bis(trifluoromethyl)benzoyl chloride (BTBC), and then add a small amount of 4-dimethylaminopyridine (DMAP ) as a catalyst, reacted with shaking at 28°C for 10 hours, evaporated the solvent to dryness under reduced pressure, and prepared the crude product by HPLC semi-preparation (MeOH / H 2 O, v / v87.5:22.5, 3ml / min) after washing for 20min, then use MeOH / H 2 O (v / v100:0, 3ml / min) was eluted for 8 min, and the fraction was collected to obtain compound 7. In the same way, when a small amount of BTBC is added (7 μl), compound 6 can be reacted, using high performance liquid phase semi-preparation (MeOH / H 2 (0, v / v80:20, 3ml / min), the peak time of collecting is 17.5min sample obtains. Using the same method, the reaction reagent BTBC was replaced by 4-nitrobenzoyl chloride (NC) and b...

Embodiment 3

[0079] Embodiment 3: Preparation of sulfur-containing chromone compounds 9-10

[0080] Weigh 2.0 mg of compound 1 and dissolve it in 0.5 mL of anhydrous pyridine, add 10 μL of Mosher reagent (R)-2-methoxy-2-trifluoromethylphenylacetyl chloride and 1.0 mg DMAP (as a catalyst) to the solution, at room temperature Reacted for 9 hours. After the solvent was evaporated to dryness under reduced pressure, the crude product was prepared by HPLC semi-preparative (MeOH / H 2 (0, v / v80:20, 3ml / min), and the collected peak time was 18.5min to obtain compound 9.

[0081] The method for preparing compound 10 is similar to that of compound 9, except that the Mosher reagent is replaced by (S)-2-methoxy-2-trifluoromethylphenylacetyl chloride.

[0082] Compounds 9 and 10 are the Mosher esterification products of compound 1. According to the nuclear magnetic resonance data and comparison with the nuclear magnetic resonance data of compound 1, the structures of compounds 9 and 10 are determined a...

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Abstract

The invention discloses a chromones compound, a preparing method thereof and chromones compound application in preparing antineoplastic and enzyme inhibitor medicines. The sulfur-containing chromones compound shown in a formula (I) is strong in effect of inhibiting the growth of lung adenocarcinoma cells or histocyte lymphoma cells or leukemia cells or gastric carcinoma cells or acute lymphoblastic leukemia cells or acute myeloblastic leukemia cells or hepatoma carcinoma cells. The chromones compound inhibits JAK3, AuroraA and ABL. The chromones compound has good application prospects in preparing the antineoplastic and the enzyme inhibitor medicines.

Description

Technical field: [0001] The invention belongs to the field of biotechnology, and in particular relates to a class of sulfur-containing chromone compounds, a preparation method thereof, and an application in the preparation of antitumor and enzyme inhibitor drugs. Background technique: [0002] Fungi can produce a variety of metabolites with different physiological activities, such as anti-tumor, anti-bacterial, anti-fungal, anti-insect, enzyme inhibitors and other biological activities. Searching for active compounds from fungi has become a hotspot in the development of natural medicines. As a class of compounds ubiquitous in nature, chromones not only have a variety of structural forms, but also have a variety of biological activities, which have attracted widespread attention from chemists. Sulfur-containing chromones are rare and less studied. Invention content: [0003] The first object of the present invention is to provide a class of sulfur-containing chromone comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61K31/381A61P35/00A61P35/02
CPCC07D495/04C12P17/18
Inventor 漆淑华鲍洁
Owner SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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