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Glycosyl beta-elemene derivatives, preparation method and application thereof

A technology for elemene and derivatives, applied in the field of medicine, can solve the problems of inability to monitor treatment in real time, difficulty in β-elemene, and limited clinical application, and achieve long excitation wavelength, high quantum yield, and good water solubility. Effect

Active Publication Date: 2017-03-22
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the shortcomings of β-elemene, such as poor solubility in water, low bioavailability, and inability to monitor and treat tumors in real time, it shows a strong dependence on concentration and time, which seriously limits its clinical application.

Method used

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  • Glycosyl beta-elemene derivatives, preparation method and application thereof
  • Glycosyl beta-elemene derivatives, preparation method and application thereof
  • Glycosyl beta-elemene derivatives, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Dissolve rhodamine B (10g) in methanol (20mL) and add ethanolamine (25mL), protect with Ar, reflux in an oil bath at 75°C until the red color disappears, cool to room temperature, add 100mL deionized water, CH 2 Cl 2 Extraction, washed with saturated brine, anhydrous Na 2 SO 4 It was dried, filtered, concentrated, and purified by silica gel column (PE / EA=4:1) to obtain off-white solid 1 (3.84 g, 35%). 1 H NMR (600MHz, CDCl 3 )δ7.92(dd, J=5.6, 3.0Hz, 1H), 7.46(dd, J=5.6, 3.1Hz, 2H), 7.09(dd, J=5.2, 3.2Hz, 1H), 6.51(d, J =8.9Hz, 2H), 6.40(d, J=2.4Hz, 2H), 6.31(dd, J=8.9, 2.4Hz, 2H), 3.51-3.47(m, 2H), 3.36(q, J=7.0Hz , 8H), 3.32-3.29(m, 2H), 1.19(t, J=7.1Hz, 12H). 13 C NMR (151MHz, CDCl 3 )δ 170.10, 153.92, 153.28, 148.90, 132.69, 130.45, 128.51, 128.14, 123.81, 122.90, 108.24, 104.80, 97.80, 65.87, 62.68, 62.66, 44.65, 44.37, 12.

[0036]

[0037] Dissolve serinol (5 g) in 150 mL of absolute ethanol, add 100 mL of BOC anhydride (12 g) in absolute eth...

Embodiment 2

[0056]

[0057] Compound 12 was obtained by a synthetic method similar to compound 6. 1H NMR (600MHz, CDCl 3 )δ7.92-7.89 (m, 1H), 7.87 (s, 1H), 7.48-7.43 (m, 2H), 7.16-7.08 (m, 2H), 6.45 (ddd, J=8.6, 5.9, 2.6Hz, 2H), 6.39(t, J=2.6Hz, 2H), 6.29(ddd, J=8.2, 5.5, 2.6Hz, 2H), 5.86(dd, J=9.3, 2.7Hz, 1H), 5.49(q, J =9.4Hz, 1H), 5.44-5.40(m, 1H), 5.38(d, J=2.8Hz, 1H), 5.15(dd, J=10.4, 7.9Hz, 1H), 4.99(dd, J=10.4, 3.5Hz, 1H), 4.65(d, J=2.9Hz, 2H), 4.55(dd, J=7.9, 2.1Hz, 1H), 4.49(d, J=12.2Hz, 1H), 4.32-4.27(m, 1H), 4.18-4.12(m, 3H), 4.06-4.03(m, 2H), 4.03-3.98(m, 1H), 3.93(dt, J=10.5, 6.1Hz, 2H), 3.69(dd, J= 14.8, 3.5Hz, 1H), 3.65-3.61(m, 3H), 3.61-3.57(m, 2H), 3.48(dd, J=14.0, 6.9Hz, 1H), 3.39-3.32(m, 10H), 3.11 (dt, J=9.4, 6.0Hz, 1H), 3.03-2.98(m, 1H), 2.41(dd, J=2.3, 1.7Hz, 1H), 2.18(s, 3H), 2.11(s, 3H), 2.09(d, J=0.6Hz, 3H), 2.08(s, 3H), 2.07(s, 3H), 1.99(s, 3H), 1.87(d, J=4.5Hz, 3H), 1.18(td, J =7.0, 1.3Hz, 12H).

[0058]

[0059] Compound 13 was obtained by a synthe...

Embodiment 3

[0063]

[0064] Dissolve 5g of trishydroxymethylaminomethane in a mixed solution composed of 30mL of methanol and 30mL of tert-butanol, add BOC anhydride (11.75g) tert-butanol (50mL) solution under stirring, react overnight at room temperature, spin off the solvent, add ethyl acetate The ester was refrigerated overnight and filtered to give 15 (8.5 g, 93%) as a white solid. 1 H NMR (600MHz, DMSO-d6) δ4.49(s, 3H), 3.52(s, 6H), 1.37(s, 9H).

[0065]

[0066] A suspension of powdered KOH (2.3 g) and dry DMF (10 mL) was cooled to 0° C. under Ar protection. After compound 15 (1.5g) was dissolved in anhydrous THF (10mL), it was added dropwise to the reaction solution. After the addition was completed, it was reacted at 0°C for 10min, and 3.3mL of propyne bromide was added dropwise, and the temperature was raised to 35°C after 5min at 0°C. ℃ react overnight, add deionized water (100mL), CH 2 Cl 2 Extraction, washed with saturated brine, anhydrous Na 2 SO 4 It was dried, fi...

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Abstract

The invention discloses glycosyl beta-elemene derivatives having general formulae I, II and III. Researches indicate that the glycosyl beta-elemene derivatives have good biological water solubility and good anti-cancer activities, can be applied to malignant tumor treatment as an anti-cancer medicine for realizing real-time tumor monitoring and treatment, and have important scientific meaning to researches and application of beta-elemene in the field of medicine. Furthermore, the invention provides a method for preparing the corresponding compounds. The method applies a click chemical reaction technology, and is simple and scientific in synthesis.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a glycosyl β-elemene derivative and a preparation method and application thereof. Background technique [0002] β-elemene is a national second-class anticancer drug extracted from the rhizome of turmeric, a plant of Zingiberaceae, for the first time by Chinese researchers. It inhibits cancer cell proliferation, induces cancer cell apoptosis, inhibits cancer cell angiogenesis, and curbs cancer cell metastasis. , affecting telomerase activity and reversing the drug resistance of cancer cells to exert anti-tumor effects. Malignant tumors also have good curative effect, broad-spectrum anti-cancer activity and good anti-tumor application prospects. However, due to the shortcomings of β-elemene, such as poor solubility in water, low bioavailability, and inability to monitor and treat tumors in real time, it has a strong concentration and time dependence, which severely limits its cli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/02C07H1/00A61K31/7056C09K11/06A61P35/00A61K49/00
CPCA61K49/0041C07H1/00C07H17/02C09K11/06C09K2211/1029C09K2211/1059C09K2211/1088
Inventor 王坚毅王勉陈政君
Owner GUANGXI UNIV
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