β-Caryophyllene-5-ester compound of furocarboxylate and its preparation method and application
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.
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Embodiment 1
[0031] Synthesis of β-Caryophyllene C1 (6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-ol):
[0032] To 6.6 mL of a 1M solution of naphthol borane in tetrahydrofuran, 4.4 mmol of β-caryophyllene was added, and the reaction was refluxed at 80 °C for 18 h, with 40 mL of CH 2 Cl 2 Dilute and cool, add 20 mL of 3M KOH and 20 mL of 30% H in turn 2 O 2 The reaction was carried out for 30 min, washed 3 times with saturated NaCl, dried, and the solvent was removed to obtain a dark yellow oily liquid, which was eluted with a 100-200 mesh silica gel column, and the mobile phase was petroleum ether:ethyl acetate=1:7 to obtain a light yellow oily liquid 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...
Embodiment 2
[0040] The synthesis method of furan-3-carboxylate β-caryophyllene-5-ester C3(6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undecan-5-ylfuran-3-carboxylate):
[0041] Dissolve furan-3-carboxylic acid 0.9 mmol and DCC 0.9 mmol in 5 mL of CH 2 Cl 2 0.9 mmol of C1 prepared in Example 1 was added and dissolved in 1 mL of CH 2 Cl 2 0.05 mmol of DMAP, reacted at room temperature for 5 h, washed, dried, and solvent removed; eluted with silica gel column to obtain 145 mg of yellow oily liquid C3. The reaction equation is as follows:
[0042]
[0043] 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),0.90-0.88 (m, 3H, CH3); 13 CNMR (CDCl 3 ,150MHz...
Embodiment 3
[0045] 1. The NO inhibition rate experiment of compounds C2 and C3:
[0046] (1) Take RAW264.7 mouse macrophages with a logarithmic growth cycle and inoculate 30,000 to 40,000 per well in a 96-well plate, at 37°C, 5% CO 2 Incubate in the incubator for 24 hours; take out the culture plate, remove the medium, and wash with PBS for 3 to 4 times;
[0047] (2) Set up the control group, LPS+dexamethasone (DIM) positive drug group and compound C2, C3 sample groups; the experimental groups are as follows:
[0048] Control group: 1. Add 50 μL of 2 μg / mL LPS and 50 μL of caryophyllene C0 with 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 concentration to each well. β-Caryophyllene C1 at 40, 20, 10, 5, and 2.5 μM, respectively;
[0049] LPS+DIM positive drug group: 50μL of 2μg / mL LPS and 50μL of DIM with concentrations of 40, 20, 10, 5, and 2.5μM were added to each well;
[0050] Compound C2 sample group: 50 μL of 2 μg / mL LPS and 50...
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