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A kind of tanshinone skeleton splicing bisindole or bispyrrole compound and its preparation method and application

A technology of tanshinone and bisindole, applied in the field of tanshinone skeleton splicing bisindole or bispyrrole compounds and its preparation, to achieve the effect of cheap raw material synthesis, good air stability and good compatibility

Active Publication Date: 2019-08-09
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In nature, indole or pyrrole alkaloids belong to an extremely abundant library of natural products, but in nature and synthetic compounds, there is no case of splicing products of bis-indole or bis-pyrrole alkaloids with tanshinone skeletons

Method used

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  • A kind of tanshinone skeleton splicing bisindole or bispyrrole compound and its preparation method and application
  • A kind of tanshinone skeleton splicing bisindole or bispyrrole compound and its preparation method and application
  • A kind of tanshinone skeleton splicing bisindole or bispyrrole compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0025] The preparation method of compound 3b-3r is the same as that of compound 3a, and the feeding ratio is the same as that of compound 3a. Compound 3b-3r can be obtained. The reaction yield is shown in Table 1 and Table 2, but it should be emphasized that the compounds of the present invention are not limited to Table 1 and Table 2. 2 represents the content.

[0026] Table 1 is the chemical structure of a kind of tanshinone skeleton splicing bisindole or bispyrrole compound

[0027]

[0028] Table 2 is the chemical structure of a kind of tanshinone skeleton splicing bisindole or bispyrrole compound

[0029]

[0030] Compound 3b prepared in this example: yellow solid, melting point: 222.9-223.4°C, yield 69%; NMR and high-resolution mass spectrometry results are as follows: 1 H NMR (DMSO-d 6 ,400MHz)δ:1.17(s,3H),2.52(s,3H),3.61(s,6H),6.78(s,2H),6.87-6.91(m,2H),7.06-7.10(m,2H) ,7.15-7.28(m,5H),7.35(d,J=8.4Hz,2H),7.81(d,J=8.8Hz 1H),8.23(d,J=8.8Hz,1H),8.37(d,J =8.4Hz,1...

Embodiment 1

[0048] Pharmacological Example 1: Cytotoxicity of compounds 3a, 3b, 3d, 3e, 3f, 3g, 3i, 3j, 3k, 3l, 3m, 3n, 3p and 3r on PC-3 cells

[0049] PC-3 (human prostate cancer) cells were cultured with RPMI-1640 medium containing 10% fetal bovine serum, 100 U / mL penicillin and 100 U / mL streptomycin. Cells were added to 96 wells at a concentration of 5000 cells per well at 37°C with 5% CO 2 Incubate for 24 hours in a humidified incubator.

[0050] Cell viability was determined by the modified MTT method. After the cells were incubated for 24 hours, the newly prepared compounds 3a, 3b, 3d, 3e, 3f, 3g, 3i, 3j, 3k, 3l, 3m, 3n, 3p and 3r were added to the dimethyl sulfoxide solution at a concentration of Gradients were added to each well so that the final concentrations of the compounds in the wells were 5 μmol / L, 10 μmol / L, 20 μmol / L, 40 μmol / L and 80 μmol / L, respectively. After 48 hours, add 10 μL of MTT (5 mg / mL) in phosphate buffered saline to each well, continue to incubate at 37°...

Embodiment 2

[0052] Pharmacological Example 2: Cytotoxicity of compounds 3a, 3b, 3d, 3e, 3f, 3g, 3i, 3k, 3l, 3m, 3n and 3r on A549 cells

[0053] A549 (human non-small cell lung cancer) was cultured with DMEM medium containing 10% fetal bovine serum, 100 U / mL penicillin and 100 U / mL streptomycin. Cells were added to 96 wells at a concentration of 4000 cells per well at 37°C with 5% CO 2 Incubate for 24 hours in a humidified incubator.

[0054] Cell viability was determined by the modified MTT method. The specific method is as in Pharmacological Example 1. IC of compound 3a on A549 tumor cells 50 It was 23.7μmol / L; the IC of compound 3b on A549 tumor cells 50 It was 77.6μmol / L; the IC of compound 3d on A549 tumor cells 50 It was 69.9μmol / L; the IC of compound 3e on A549 tumor cells 50 It was 45.6μmol / L; the IC of compound 3f on A549 tumor cells 50 It was 39.1 μmol / L; the IC of compound 3g on A549 tumor cells 50 It was 43.6μmol / L; the IC of compound 3i on A549 tumor cells 50 It was ...

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Abstract

The invention discloses a tanshinone framework spliced bisindole or bispyrrole compound. The tanshinone framework spliced bisindole or bispyrrole compound is prepared by adding substituted indole or substituted pyrrole and tanshinone, according to the mol ratio of 3 to 1, into a polar solvent acetonitrile, and carrying out addition reaction for 72h under the condition of heating at 50 DEG C. A framework contains a multi-bioactivity tanshinone framework and a bisindole or bispyrrole alkane framework, and can provide a compound source for bioactivity screening; the tanshinone framework spliced bisindole or bispyrrole compound has important application value in screening of multi-target multipurpose drugs and a pharmaceutical industry. The tanshinone framework spliced bisindole or bispyrrole compound has the advantages that the operation is simple and feasible; the synthesis of raw materials is cheap and easy to realize, and can be carried out in various polar organic solvents; the tanshinone framework spliced bisindole or bispyrrole compound also has relatively good air stability and wide applicability, and has good compatibility on various substituent groups; the compound has a potential of being developed into an anti-tumor drug.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a bisindole or bispyrrole compound spliced ​​with a tanshinone skeleton and a preparation method and application thereof. Background technique [0002] The splicing of bioactive natural product scaffolds into other bioactive natural product scaffolds is an extremely important research area in organic and medicinal chemistry. (1) Bisindole or bispyrrolidine compounds widely exist in multiple drug active molecules, and have biological activities such as anti-inflammatory, anti-tumor, and anti-oxidation. (2) Tanshinone is derived from the root of the traditional Chinese medicine Salvia miltiorrhiza, and has multiple drug activities. The main representative active ingredients include: Tanshinone I, TanshinoneIIA, Dihydrotanshinone, Dihydrotanshinone I and Cryptotanshinone. In view of the fact that tanshinone skeleton compounds and bisindole or bispyrrole compounds have m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J73/00A61P35/00A61P35/02
CPCC07J73/003
Inventor 刘雄利陈智勇余章彪周玥俸婷婷周英彭礼军田民义张敏
Owner GUIZHOU UNIV
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