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Furoic acid beta-caryophyllene-5-ester compound as well as preparation method and application of furoic acid beta-caryophyllene-5-ester compound

A technology of ester compounds and furan formic acid, applied in organic chemistry, drug combination, antitumor drugs, etc., can solve the problem that β-caryophyllene derivatives do not have much breakthrough progress, and the biological activity research of β-caryophyllene derivatives There are no outstanding reports and other problems, and the effects of good inhibitory activity, simple reaction steps and good application prospects are achieved.

Active Publication Date: 2020-02-18
NANJING FORESTRY UNIV
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  • Description
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  • Application Information

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Problems solved by technology

[0004] However, the current research on β-caryophyllene derivatives still has not made much breakthrough progress, which has led to no outstanding reports on the biological activities of β-caryophyllene derivatives.

Method used

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  • Furoic acid beta-caryophyllene-5-ester compound as well as preparation method and application of furoic acid beta-caryophyllene-5-ester compound
  • Furoic acid beta-caryophyllene-5-ester compound as well as preparation method and application of furoic acid beta-caryophyllene-5-ester compound
  • Furoic acid beta-caryophyllene-5-ester compound as well as preparation method and application of furoic acid beta-caryophyllene-5-ester compound

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 React for 30 minutes, wash with saturated NaCl for 3 times, dry, and remove the solvent to obtain a dark yellow oily liquid, which is eluted with a 100-200 mesh silica gel column, mobile phase petroleum ether: ethyl acetate = 1: 7, and a light yellow oily liquid C1 is obtained . 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...

Embodiment 2

[0041] Synthetic method of furan-3-carboxylic acid β-caryophyllene-5-ester C3 (6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-ylfuran-3-carboxylate):

[0042] Dissolve furan-3-carboxylic acid 0.9 mmol and DCC 0.9 mmol in 5 mL of CH 2 Cl 2 , react at 0°C for 30min; add C10.9mmol prepared in Example 1 and dissolve in 1mL CH 2 Cl 2 DMAP 0.05mmol, reacted at room temperature for 5h, washed, dried, and solvent removed; eluted through a silica gel column to obtain 145mg of yellow oily liquid C3. The reaction equation is as follows:

[0043]

[0044] C3 1 HNMR (600M, CDCl 3 )δ: 8.00 (d, 1H, -CH, J = 6Hz), 7.41 (d, 1H, -CH, J = 1.2Hz), 6.75-6.73 (m, 1H, -CH), 4.97-4.90 (m, 2H, =CH2), 2.52-2.42(m, 1H, CH), 2.33-2.30(m, 1H, CH), 2.13-2.10(m, 1H, CH), 2.03-1.98(m, 1H, CH), 1.86-1.83(m, 1H, CH), 1.79-1.76(m, 2H, CH2), 1.66-1.63(m, 2H, CH2), 1.621.60(m, 2H, CH2), 1.42(s, 1H, CH), 1.26(d, 1H, CH, J=18Hz), 1.02(s, 3H, CH3), 0.99(s, 3H, CH3), 0.96(d, 1H, CH, J=12Hz), 0.90-0.8...

Embodiment 3

[0046] 1. NO inhibition rate experiment of compounds C2 and C3:

[0047] (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;

[0048] (2) Set the control group, LPS+dexamethasone (DIM) positive drug group and compound C2, C3 sample groups; the experimental groups are as follows:

[0049] 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;

[0050] 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;

[0051] Compound C2 sample group: add 50 μL of 2 μg / mL LPS and 50 μL of C2 at concentrat...

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Abstract

The invention discloses a furancarboxylic 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-caryophyllenol ester. The preparation method of the furoic acid beta-caryophyllene-5-ester compound comprises the following steps: reacting furoic acid with DCC, adding beta-caryophyllenol and DMAP, and reacting to obtain the compound after the reaction is finished. NO inhibition rate experiments, cytotoxicity experiments and anti-cancer activity experiments prove that the compoundshave a certain inhibition effect on inflammation, have good anti-cancer activity on cervical cancer, liver cancer, breast cancer or lung cancer, and can be applied to preparation of anti-inflammatoryand anti-cancer drugs.

Description

technical field [0001] The invention belongs to the technical field of preparation of β-caryophyllene carboxylic acid esters, and in particular relates to β-caryophyllene-5-furanoic acid ester compounds and their preparation methods and applications. Background technique [0002] Cancer is a major disease facing mankind today. The current treatment methods are mostly surgery, radiation therapy and chemotherapy. However, the side effects of chemical drug therapy have always troubled people, and it is urgently needed to develop anticancer drugs with high efficiency and low toxicity. The development of anticancer drugs from natural products has attracted much attention, among which many terpenoids such as paclitaxel (Shu, X., et al. Colloids and Surfaces B: Biointerfaces, 2019.182: p.110356.doi.org / 10.1016 / j.colsurfb.2019.110356), Ganoderma acid (Zhang, W., et al.,. Artif Cells Nanomed Biotechnol, 2019.47(1): p.406-419.doi.org / 10.1080 / 21691401.2018.1559177), Ginkgo lactone ...

Claims

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Application Information

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IPC IPC(8): C07D307/68A61P29/00A61P35/00
CPCC07D307/68A61P29/00A61P35/00
Inventor 徐莉史久洲卢雯
Owner NANJING FORESTRY UNIV
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