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Morusin skeleton splicing convolutamydine A skeleton compound and its preparation method and application

A technology of compounds and skeletons, applied in the field of chemistry, to achieve the effects of easy-to-obtain raw material synthesis, cheap raw material synthesis, and good air stability

Active Publication Date: 2019-05-10
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In nature, flavonoids and oxindole alkaloids belong to two extremely abundant natural product libraries, but in nature and synthetic compounds, there is no case containing the flavonoid skeleton and oxindole alkaloid skeleton of these two natural products Splicing product

Method used

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  • Morusin skeleton splicing convolutamydine A skeleton compound and its preparation method and application
  • Morusin skeleton splicing convolutamydine A skeleton compound and its preparation method and application
  • Morusin skeleton splicing convolutamydine A skeleton compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0020] The preparation method of compound 3b-3w is the same as that of compound 3a, and the feeding ratio is the same as that of compound 3a. Compound 3b-3w can be obtained. The reaction yield is shown in Table 1 and Table 2, but it should be emphasized that the compound of the present invention is not limited to Table 1 and Table 2 2 represents the content.

[0021] Table 1 is the chemical structure of a Morusin skeleton splicing convolutamydine A skeleton compound

[0022]

[0023] Table 2 is the chemical structure of a Morusin skeleton splicing convolutamydine A skeleton compound

[0024]

[0025] Compound 3b prepared in this example: yellow solid, melting point: 75.6-76.2 o C, productive rate 62%; Results such as NMR and high-resolution mass spectrometry test are as follows: 1 H NMR (CDCl 3 , 400 MHz) δ : 1.46 (s, 6H), 2.26 (s,3H), 2.62-2.66 (m, 2H), 2.76-2.79 (m, 2H), 2.93 (d, J = 12.1 Hz, 1H), 3.15(d, J = 12.5 Hz, 1H), 4.80-4.90 (m, 2H), 5.62 (d, J = 7.8...

Embodiment 1

[0048] Pharmacological Example 1: Cytotoxicity of Compounds 3b-3w (excluding 3l) to K562 Cells

[0049] K562 (human chronic myeloid leukemia cells) were cultured in 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.

[0050] Cell viability was determined by the modified MTT method. After the cells were incubated for 24 hours, the newly prepared dimethyl sulfoxide solution of compounds 3b-3w (excluding 3l) was added to each well in a concentration gradient, so that the final concentrations of the compounds in the wells were 3 μmol / L , 6 μmol / L, 13 μmol / L, 25 μmol / L and 50 μmol / L. After 48 hours, 10 μL of MTT (5 mg / mL) in phosphate buffer was added to each well, and then continued at 37 o C After 4 hours of incubation, centrifuge for 5 minutes to remove unconverted MTT, and add 150 μL dimethyl ...

Embodiment 2

[0052] Pharmacological Example 2: Cytotoxicity of Compounds 3b, 3d, 3e, 3j, 3r and 3v on PC-3 cells

[0053] PC-3 (human prostate cancer) cells were cultured in RPMI-1640 medium containing 10% fetal bovine serum, 100U / mL penicillin and 100U / mL streptomycin. Cells were added to 96 wells at a concentration of 5000 cells per well, at 37 o C with 5% CO 2 Incubate for 24 hours in a humidified incubator.

[0054] Cell viability was determined by the modified MTT method. After the cells were incubated for 24 hours, newly prepared dimethyl sulfoxide solutions of compounds 3b, 3d, 3e, 3j, 3r and 3v were added to each well in a concentration gradient, so that the final concentrations of the compounds in the wells were 3 μmol / L, 6 μmol / L, 13 μmol / L, 25 μmol / L and 50 μmol / L. After 48 hours, 10 μL of MTT (5 mg / mL) in phosphate buffer was added to each well, and then continued at 37 o C After 4 hours of incubation, centrifuge for 5 minutes to remove unconverted MTT, and add 150 μL dime...

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Abstract

The invention discloses a Morusin skeleton spliced convolutamydine A skeleton compound. Various substituted butanone containing Morusin skeletons and various substituted isatin react for 15 h at the reaction temperature of 40 DEG C in ethyl alcohol according to the molar ratio of 3:4, Aldol addition reaction is conducted, and the Morusin skeleton spliced convolutamydine A skeleton compound is obtained. Skeletons of such kind contain multi-bioactivity Morusin skeletons and convolutamydine A skeletons, compound sources can be provided for bioactivity, and the skeletons have important application value in the screening and pharmaceutical industry of multi-target-spot multipurpose medicine. Operation is easy to implement, raw materials are low in synthesis cost and easy to obtain, synthesis can be conducted in various polar organic solvents, air stability is good, the application range is wide, the compound has good compatibility with various substituted groups, and the compound has the potential to be developed into anti-tumor medicine.

Description

technical field [0001] The invention relates to the field of chemical technology, in particular to a Morusin skeleton spliced ​​convolutamydine A skeleton compound, 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) The flavonoid skeleton compound Morusignin L and Morusin II (Morusignin L I and Morusin II) are two active ingredients separated from the traditional Chinese medicine Morusin alba, which occupy an important position in the field of flavonoids, that is, they have significant biological activity (anti-inflammatory, diuretic, expectorant, and anti-hepatitis B activity). (2) Alkaloids containing the skeleton of Convolutamydine A also exist in some biologically active compounds or natural products, representative examples of selectivity include: Convolutamydine A III...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04A61P35/00
CPCC07D493/04
Inventor 刘雄利周英陆毅黄俊飞俸婷婷林冰田民义彭礼军余章彪
Owner GUIZHOU UNIV
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