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Rakicidin derivatives, and preparation method and application thereof in preparation of anticancer drugs

A technology for derivatives and cancer, which is applied in the field of Rakicidin derivatives, preparation of Rakicidin derivatives, and preparation of drugs for treating cancer. It can solve the problems of low total yield, poor stability, and long total synthesis route, etc.

Active Publication Date: 2019-07-02
新沂尚德药缘药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the total synthetic route of such compounds is long, the total yield is low and the stability is relatively poor

Method used

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  • Rakicidin derivatives, and preparation method and application thereof in preparation of anticancer drugs
  • Rakicidin derivatives, and preparation method and application thereof in preparation of anticancer drugs
  • Rakicidin derivatives, and preparation method and application thereof in preparation of anticancer drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: Synthesis of Rakicidin derivatives and salts thereof

[0016] Please refer to the appendix of the manual for the specific synthetic route figure 2 with instructions attached image 3 ,Specific steps are as follows:

[0017] Under argon protection, tetrahydrofuran (350mL) solution of compound 8 (35.7g, 70.0mmol) was added successively with tetrakistriphenylphosphopalladium (16.19g, 14mmol) and N-methylaniline (15g, 140mmol), at room temperature The reaction was stirred for 1.5 h, and the reaction solution was diluted with ethyl acetate (500 mL). The organic phase was washed twice with 1% HCl (120 mL). The obtained organic phase was dried with anhydrous sodium sulfate, filtered and concentrated, and the obtained crude product was purified by silica gel column to obtain colorless oily compound 2 (30.25g, 92%)

[0018] In a 250mL round bottom flask, compound 2 (19.2g, 40.88mmol), allyl sarcosinate (7.92g, 61.32mmol) and 160mL of dichloromethane obtained i...

Embodiment 2

[0042] Example 2: Normoxic and Hypoxic Biological Activities of Rakicidin Derivatives on Human Pancreatic Cancer Cell Lines Panc-1, ASPC-1 and PATU8988

[0043] Make 2×10 cells to be tested 5 / mL cell suspension, add to 96-well plate round-bottom cell culture plate, add the compound to be tested respectively, 3 wells for each test concentration, place at 37°C, 5% CO 2 After culturing for 72 hours under saturated humidity conditions, the absorbance (A) value was measured at a wavelength of 570 nm in an enzyme-linked detector by the MTT method, and the inhibitory effect of the compound of the present invention on test cancer cells was calculated.

[0044] Table 1.Inhibitory activity of Rakicidin derivatives on various pancreatic cancer cells (IC 50 , μM)

[0045]

[0046] As shown in Table 1, the tested compounds showed strong anticancer activity against the tested cancer cell lines.

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Abstract

The invention provides Rakicidin derivatives represented by the formula (I), and a preparation method and an application thereof in preparation of anticancer drugs.

Description

technical field [0001] The invention provides a Rakicidin derivative, and relates to a preparation method of the Rakicidin derivative and its use in preparing medicines for treating cancer. The invention belongs to the technical field of medicines. Background technique [0002] Rakicidin is produced by Micromonas NO.R385-2a (Monas genus), and it is a general term for a series of compounds with anticancer activity. Rakicidin series compounds are cyclic lipopeptide compounds containing 15-membered rings. [0003] According to the difference of the R group, the compound is named as six natural products of Rakicidin A, Rakicidin B, Rakicidin C, Rakicidin D, Rakicidin E and Rakicidin F, and their structures are shown in the appendix of the description figure 1 . It is reported that the BE-43547 series of compounds are effective against K562, K562 / G + 、Ba / F3cells expressing BCR-ABLT 315I and PANC-1 and other cancer cells have inhibitory activity. In 2016, Poulsen et al. explo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/027A61K38/06A61K45/06A61P35/00
CPCC07K5/0205A61K38/06A61K45/06A61K38/00A61K2300/00
Inventor 陈悦张泉丁亚辉陈健王蒙蒙李洪波
Owner 新沂尚德药缘药业有限公司
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