Beta-caryophyllene derivative as well as preparation method and application thereof

A kind of technology of caryophyllene and derivative, applied in β-caryophyllene derivative and field of preparation and application thereof

Active Publication Date: 2018-03-02
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In these studies, the role of trans-cyclononene is often overlooked

Method used

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  • Beta-caryophyllene derivative as well as preparation method and application thereof
  • Beta-caryophyllene derivative as well as preparation method and application thereof
  • Beta-caryophyllene derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] For the reaction flow chart, see figure 2 .

[0067] intermediate

[0068] (6aR,8aS)-1-methoxy-4a,7,7-trimethyl-9-methylene-1,4-di(pyridin-2-yl)-2,4a,5,6,6a,7,8,8a ,9,10,11,11a-dodecahydro-1H-cyclobuta[5,6]cyclonona[1,2-d]pyridazine(5) Synthesis

[0069] For the reaction flow chart, see figure 2 .

[0070]

[0071] Compound 1β-caryophyllene (33.7mg, 0.165mmol) was dissolved in dry methanol solution (3ml), and tetrazine compound 2 (35.3mg, 0.150mmol) was added thereto at room temperature. Stirred at room temperature for four hours, the yellow color faded, indicating The tetrazine raw material is consumed. The solvent was suspended under reduced pressure, and the residue was separated by column chromatography (dichloromethane:methanol=20:1, v / v) to obtain 53.2 mg of a light yellow oily liquid.

[0072] Structural Confirmation Data: 1 H NMR (400MHz, MeOD) δ8.61 (dd, J = 4.9, 0.9Hz, 1H), 8.55 (d, J = 4.5Hz, 1H), 7.90–7.85 (m, 2H), 7.73 (d, J = 8.0Hz,1H),7.46–7....

Embodiment 2

[0079] The synthesis of embodiment 2 compound 12

[0080]

[0081] Compound (4R,6R)-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.0 4,6 Synthesis of ]dodecane(7)

[0082] Its reaction flow chart sees image 3

[0083]

[0084] Compound 1β-caryophyllene (5.5ml, 5g, 24.45mol) was dissolved in dry dichloromethane solution (35ml), and 15% NaHCO was added at room temperature 3 (68ml), after stirring evenly, slowly add mCPBA (7.4g, 36.675mmol), after stirring for two hours, quench the reaction with 15% NaOH solution (100ml), the organic phase was washed with saturated brine (100ml×3), the obtained organic The phase was dried over anhydrous sodium sulfate and recrystallized to obtain 3.48 g of white solid (compound 7), with a yield of 66%.

[0085] Structural Confirmation Data: 1 H NMR (400MHz, CDCl 3 )δ4.97(s,1H),4.86(s,1H),2.88(dd,J=10.6,4.2Hz,1H),2.62(dd,J=18.8,9.5Hz,1H),2.34(ddd,J =12.6,8.1,4.4Hz,1H),2.25(ddd,J=16.7,8.1,4.3Hz,1H),2.15–2.05(m,2H),1.76(t,J=9.9Hz,1H),...

Embodiment 3

[0103] Example 3, Cytotoxicity Test of β-Caryophyllene and Its Derivatives (Compound 11)

[0104] Hela cells were incubated with different concentrations of β-caryophyllene and compound 11 (5 μM, 10 μM, 25 μM, 50 μM, 100 μM, 250 μM, 500 μM) in methanol solution, and after 24 hours, the cell survival was measured by the MTT method. The experimental results are as follows Figure 4 As shown, this experiment was repeated three times.

[0105] Depend on Figure 4 It can be seen that at the highest concentration of 500 μM, there is still no obvious adverse effect on the growth of cells. This experiment proves that β-caryophyllene and its derivatives are slightly toxic as reactants.

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PUM

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Abstract

The invention discloses a beta-caryophyllene derivative as well as a preparation method and application thereof. The structural general formula of the beta-caryophyllene derivative provided by the invention is shown by a formula I, wherein R is selected from any one of the following groups: a hydroxy group, an amino group, an ester group and an amide group. The inventor of the invention has verified through experiments that a reaction factor has good reactivity, stability, easily available raw materials and a certain reaction rate at the same time. The application of this reaction factor is proved in corresponding protein labeling and cell labeling experiments, which provides a new idea for the development of related biorthogonal reaction factors.

Description

technical field [0001] The invention relates to a β-caryophyllene derivative, a preparation method and application thereof. Background technique [0002] In recent years, bioorthogonal reactions have made great progress in the study of the structure, function and interaction of biomacromolecules (including proteins, nucleic acids, sugars, etc.), especially in the real-time tracking of these biomacromolecules in living cells. Development [J.A.Prescher and C.R.Bertozzi, Nature chemical biology 2005, 1, 13-21.]. A bioorthogonal reaction refers to a chemical reaction that can occur under physiological conditions in an organism without interfering with other biochemical reactions occurring simultaneously in the body, and without causing damage to the organism and target biomolecules [E.M. Sletten and C.R. Bertozzi, Angewandte Chemie International Edition 2009, 48, 6974-6998.]. The main factors for evaluating bioorthogonal reactions are the activity and stability of the reactant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/00C07C31/137C07D237/26C07D207/46
CPCC07C29/00C07C31/137C07D207/46C07D237/26C07D301/00C07D301/14C07D303/04C07D303/12C07D303/14C07F7/1804C07F7/1892Y02P20/55
Inventor 唐叶峰曹玉吴云飞
Owner TSINGHUA UNIV
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