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A 1,2,3-triazole-substituted bisphenylpyrone compound and its preparation method and application

A kind of biphenylpyrone and compound technology, applied in the field of medicine, can solve the problems such as structure and activity that have not been reported and the like

Active Publication Date: 2018-05-15
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention uses bisphenylpyrone as the basic core and introduces different nitrogen heterocycles at the 3-position: 1-hydroxyl-3-(1H-1,2,3-triazol-4-yl)bis Phenylpyrone compounds have good antitumor activity, but their structure and activity have not been reported so far

Method used

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  • A 1,2,3-triazole-substituted bisphenylpyrone compound and its preparation method and application
  • A 1,2,3-triazole-substituted bisphenylpyrone compound and its preparation method and application
  • A 1,2,3-triazole-substituted bisphenylpyrone compound and its preparation method and application

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Embodiment 1

[0039] The synthesis of embodiment 1 compound of the present invention

[0040] The preparation reaction scheme of compound of the present invention is as follows:

[0041]

[0042] Scheme Reagents and conditions: (a)P 2 o 5 / CH 3 SO 3 H 85℃, 2.5h; (b) Propargylbronide, L 2 CO 3 , SMF, 4h; (c) Corresponding benzyl azide, DMSO, CuSO 4 .5H 2 O, rt, 16h.

[0043] The specific preparation method of the compound involved in the described reaction scheme route is as follows:

[0044] (1) Synthesis of 1,3-dihydroxybisphenylpyrone (4)

[0045] 2-Hydroxysalicylic acid (6.9g, 0.05mol) and phloroglucinol (6.3g, 0.05mol) were dissolved in Eaton's reagent, stirred and reacted at 85°C for 4 hours, the reaction was complete, cooled to room temperature, and an appropriate amount of ice water was added Excessive acid was quenched, stirred for 2 hours and left to stand, filtered, dissolved in ethyl acetate, washed with water until neutral, dehydrated with anhydrous sodium sulfate, ...

Embodiment 2

[0055] The pharmacological experiment of embodiment 2 compounds of the present invention

[0056] (1) Experimental materials

[0057] 1. Test sample

[0058] After the target compounds were dissolved in DMSO (Merck), PBS (-) was added to make a 1000 μg / ml solution or a homogeneous suspension, and then diluted with DMSO-containing PBS (-).

[0059] 2. Cell lines

[0060] A549 (human non-small cell lung cancer cells).

[0061] 3. Other materials and main instruments

[0062] Culture medium: RPMI1640 + 15% NBS + double antibody; MTT: [thiazolyl blue] was purchased from Sigma Company (St.Louis, MO, USA); other reagents were domestic analytical grade. Fully automatic microplate reader WellscanMK-2 (Labsystems company), CO 2 Constant temperature incubator (Japan Sanyo Company), imported 96-well culture plate, etc.

[0063] 4. Experimental method

[0064] MTT (tetrazolium salt) method: 96-well plate per hole concentration is 4 ~ 6 × 10 4 cells / ml cell suspension 100 μl, set a...

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Abstract

The invention relates to 1,2,3-triazole substituted diphenyl pyrone compounds, and the structural formula of the compounds is represented in the description; wherein the substituent R represents halogen, an alkyl group, or an electrophilic substituent, and the R can be positioned on the ortho-position, meta-position, or para-position of a phenyl ring. The invention also relates to preparation and antitumor applications of the 1,2,3-triazole substituted diphenyl pyrone compounds. The compounds have strong inhibiting activity on tumor cells, and can be used to treat tumors.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 1,2,3-triazole-substituted bisphenylpyrone compound and a preparation method and application thereof. Background technique [0002] Tumor is one of the diseases that seriously endanger human health. According to data from the Chinese Medical Association in 2007, malignant tumors have become the number one killer among various diseases that endanger the lives of Chinese residents. In China, 2 million people die of tumors every year. Chemotherapy is one of the three major methods of cancer treatment. After years of hard work, some cancers can now be cured by drug chemotherapy. The currently used anti-tumor drugs have serious side effects: (1) The selectivity to tumor cells is not strong, and while killing tumor cells, it also damages normal cell nucleus tissue; (2) Tumor cells develop drug resistance to anti-tumor drugs . This is an urgent problem to be solved in tumor drug th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A61P35/00
CPCC07D405/12
Inventor 俞世冲吴俊琪王静侯楠黄蕾柴晓云程浩王姝怡章越凡李铁军吴秋业
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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