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A kind of fluorinated camptothecin drug derivative and its preparation and application

A technology for fluorinated camptothecin and its derivatives, which is applied in the field of fluorinated camptothecin drug derivatives and their preparation and application, and can solve the problem of reducing the progress of research on the modification of phenolic compounds, many method steps, and low reaction yields, etc. problems, to achieve the effect of mild reaction conditions, simple operation process and high reaction efficiency

Active Publication Date: 2021-05-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conditions of this kind of method are relatively harsh, and there are many steps in the method, and the reaction yield is low. These problems have greatly reduced the progress of the research on the modification of phenolic compounds.

Method used

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  • A kind of fluorinated camptothecin drug derivative and its preparation and application
  • A kind of fluorinated camptothecin drug derivative and its preparation and application
  • A kind of fluorinated camptothecin drug derivative and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of compound (I)

[0031]

[0032] Add 1 mmol of camptothecin derivative SN-38 to 4 ml of 10% (w / w) acetic acid aqueous solution, add 1.5 mmol of Selectfluor, 0.05 mmol of Eosin Y, and react under 12W blue light irradiation at room temperature for 6 hours. After the reaction, the reaction liquid Saturated NaCl aqueous solution was added to the solution, extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain the crude compound. The crude compound was subjected to silica gel column chromatography, using a solution of ethyl acetate and petroleum ether with a volume ratio of 1:9 as the mobile phase, and the eluent with an Rf value of 0.3 to 0.5 was tracked and collected by TLC, and the collected eluent was passed through The solvent was removed under reduced pressure and dried to obtain 252 mg (yield 70%) of the pure compound shown in form...

Embodiment 2

[0034] Embodiment 2: Antitumor activity detection of compound (I)

[0035] The tumor cell Hela (cervical cancer cell) was selected, and the anti-proliferation activity of the tumor cell was detected by the MTT method. Cells were seeded at a concentration of 4000-5000 cells / well into a 96-well plate containing 10% fetal bovine serum in 1640 culture medium, and a note was added on the plate cover, and the cells were stored in 5% CO 2 , Cultivate at 37 DEG C for 12 hours, treat that the cells adhere to the wall on the 96-well plate, add the drug to be tested (compound (I) prepared in Example 1) with a pipette gun in the aseptic operating table, so that the drug concentration in each well is 0.01 μM, 0.1μM, 1μM, 10μM, 100μM five concentration gradients, each concentration set up five parallel groups, with anti-tumor drug SN-38 as a control), and put the 96-well plate in 5% CO 2 , and cultured at 37°C for 24 hours. Take out the 96-well plate, add 10 μL of MTT kit reagents (purcha...

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Abstract

The invention relates to a fluorinated camptothecin drug derivative and its preparation and application. The compound of the present invention is prepared by direct fluorination of phenol with organic photocatalysis. The operation process is simple, the reaction conditions are mild, the site selectivity is high, and the reaction is efficient. It can be prepared in one step. The compound has good antitumor activity and is Antineoplastic drugs provide a new solution.

Description

[0001] (1) Technical field [0002] The invention relates to a fluorinated camptothecin-containing drug-like derivative, a preparation method thereof, and an application thereof in the preparation of antitumor drugs. [0003] (2) Background technology [0004] Phenol is an important basic organic raw material, and many of its downstream products are involved in many fields, mainly used in the manufacture of phenolic resin, bisphenol A and caprolactam. Phenol derivatives such as halogenated phenols, nitrophenols, and alkylphenols can be used in the production of medicines, pesticides, paints, dyes, explosives, and spices. Phenolic compounds widely exist in nature, and spices and many natural products contain phenolic structures. The traditional method for modifying phenolic compounds is: first protect the hydroxyl group, then modify other positions of the hydroxyl group, and finally deprotect to realize the modification. The conditions of this type of method are relatively har...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/22A61P35/00
CPCA61P35/00C07D491/22
Inventor 朱勍刘江窦言东
Owner ZHEJIANG UNIV OF TECH
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