Pyrazinecarboxylic acid beta-caryophyllene-5-ester compound as well as preparation method and application thereof

An ester compound, pyrazinecarboxylic acid technology, applied in the directions of organic chemistry, drug combination, antipyretics, etc., can solve the problems such as no reports, and achieve the effects of good inhibitory activity, simple reaction steps, and good application prospects.

Pending Publication Date: 2020-02-28
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the research on natural molecules has attracted much attention, but the introduct

Method used

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  • Pyrazinecarboxylic acid beta-caryophyllene-5-ester compound as well as preparation method and application thereof
  • Pyrazinecarboxylic acid beta-caryophyllene-5-ester compound as well as preparation method and application thereof
  • Pyrazinecarboxylic acid beta-caryophyllene-5-ester compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis method of β-caryophyllene alcohol C1 (6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-ol):

[0032] Add 4.4mmol of β-caryophyllene to 6.6mL of 1M solution of catecholborane in tetrahydrofuran, reflux at 80°C for 18h, and use 40mL of CH 2 Cl 2 Dilute and cool, add 20mL 3M KOH and 20mL 30% H 2 o 2 , reacted for 30 min, washed 3 times with saturated NaCl, dried, and desolventized to obtain a dark yellow oily liquid, which was eluted with a 100-200 mesh silica gel column, mobile phase petroleum ether: ethyl acetate=1: 7, and a light yellow oily liquid was obtained C1. The reaction process is as follows:

[0033]

[0034] C1 1 HNMR (600M, DMSO-d 6 ) δ: 4.83 (d, 2H, =CH 2 , J=6Hz), 4.22(d, 1H, -OH, J=6Hz), 3.32(s, 1H, -CH), 2.46-2.42(m, 1H, -CH), 2.22-2.12(m, 2H, -CH 2 ), 1.92-1.86 (m, 1H, -CH), 1.74-1.71 (m, 2H, -CH 2 ), 1.70 (t, 1H, -CH, J=6Hz), 1.58-1.53 ​​(m, 1H, -CH), 1.51-1.48 (m, 2H, -CH 2 ), 1.44-1.39 (m, 2H, -CH 2 ), 0.38(s, 3H, -CH ...

Embodiment 2

[0041] 1. NO inhibition rate experiment of compound C2:

[0042] (1) Take the mouse macrophage RAW264.7 with a logarithmic growth cycle, seed it in a 96-well plate at 30,000 to 40,000 per well, at 37°C, 5% CO 2 Incubate in an incubator for 24 hours; take out the culture plate, remove the medium, and wash with PBS for 3 to 4 times;

[0043] (2) Set up the control group, LPS+dexamethasone (DIM) positive drug group and compound C2 sample group; the experimental groups are as follows:

[0044] Control group: 1. Add 50 μL of 2 μg / mL LPS and 50 μL of caryophyllene CO at concentrations of 40, 20, 10, 5, and 2.5 μM to each well; 2. Add 50 μL of 2 μg / mL LPS and 50 μL of LPS to each well β-caryophyllenol C1 at 40, 20, 10, 5, 2.5 μM, respectively;

[0045] LPS+DIM positive drug group: Add 50 μL of 2 μg / mL LPS and 50 μL of DIM with concentrations of 40, 20, 10, 5 and 2.5 μM to each well;

[0046] Compound C2 sample group: add 50 μL of 2 μg / mL LPS and 50 μL of C2 at concentrations of 40...

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Abstract

The invention discloses a pyrazinecarboxylic acid beta-caryophyllene-5-ester compound as well as a preparation method and application thereof, and belongs to the technical field of preparation of carboxylic acid beta-caryophyllene-5-ester. The preparation method of pyrazinecarboxylic acid beta-caryophyllene-5-ester compound comprises the steps: pyrazinecarboxylic acid firstly is reacted with DCC,then beta-caryophyllenol and DMAP are added for reaction, and the pyrazinecarboxylic acid beta-caryophyllene-5-ester compound is obtained after the reaction is finished. It is proved by NO inhibitionratio experiments, cytotoxicity experiments and anticancer activity experiments that the pyrazinecarboxylic acid beta-caryophyllene-5-ester compound has good activity on inflammatory RAW264.7 cell strains and cervical cancer, liver cancer, breast cancer or lung cancer, and can be applied to preparation of anti-inflammatory and anti-cancer drugs.

Description

technical field [0001] The invention belongs to the technical field of β-caryophyllene-5-carboxylates, in particular to pyrazinecarboxylic acid β-caryophyllene-5-ester compounds and their preparation methods and applications. Background technique [0002] In the process of medical research and development, heterocyclic compounds have been widely concerned by researchers because of their good biological activity. From recent literature reports, it is not difficult to find that the introduction of heterocyclic compounds into the parent structure is beneficial to improve the biological activity of the parent compound (Zhao, F., et al., MedChemComm, 2018.9(12): p.2091-2099 ; Katariya, K.D., t al., Bioorganic Chemistry, 2019: p.103406.). Among them, nitrogen-containing heterocyclic compounds are particularly prominent, because nitrogen-containing heterocyclic compounds are structurally similar to alkaloids in organisms, which enable them to have high specificity for targets and ...

Claims

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Application Information

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IPC IPC(8): C07D241/24A61P29/00A61P35/00
CPCC07D241/24A61P29/00A61P35/00
Inventor 徐莉史久洲卢雯
Owner NANJING FORESTRY UNIV
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