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28-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthesis methods and application thereof

A synthesis method and technology of phenylalanine are applied in the directions of drug combinations, medical preparations containing active ingredients, pharmaceutical formulas, etc. to achieve the effects of good proliferation inhibitory activity and good medicinal value.

Inactive Publication Date: 2019-03-26
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no relevant report on the use of 28-(L-phenylalanine)-pentacyclic triterpene derivatives in the treatment of tumors

Method used

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  • 28-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthesis methods and application thereof
  • 28-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthesis methods and application thereof
  • 28-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthesis methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of compound 1

[0033]

[0034] 3-Propionyloxy-oleanolic acid (0.50 g, 1.0 mmol) was dissolved in CH 2 Cl 2 (10mL), add dropwise SOCl 2 (0.45mL), reflux at 72°C for 2h, the reaction solution was concentrated under reduced pressure, and washed with CH 2 Cl 2 (2×20mL) spin off SOCl 2 ; The resulting residue was dissolved in CH 2 Cl 2(20mL), add L-phenylalanine methyl ester (0.26g, 1.5mmol) and saturated aqueous sodium bicarbonate solution (1.25mL) successively under ice-bath conditions, stir and react at room temperature for 12h; the obtained reaction material is dispersed in 1mol / L HCl (100mL), CH 2 Cl 2 (3×30 mL), combined the organic layers, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried to obtain a crude product. The crude product was separated by silica gel column chromatography (eluent: V 石油醚 :V 乙酸乙酯 =30:1to5:1), to obtain compound 1 (0.48g, 73.0%, white ...

Embodiment 2

[0036] Embodiment 2: the synthesis of compound 1

[0037] Dissolve 3-propionyloxy-oleanolic acid (0.50 g, 1.0 mmol) in a mixed solvent composed of MeOH and THF (5 mL each of MeOH and THF), add dropwise oxalyl chloride (0.45 mL), and reflux at 60 ° C for 1 h , the reaction solution was concentrated under reduced pressure, and MeOH (2×20mL) was used to spin off oxalyl chloride; the obtained residue was dissolved in MeOH (20mL), and L-phenylalanine methyl ester (0.26g, 1.5mmol), Saturated potassium carbonate aqueous solution (1.25mL), stirred and reacted at 50°C for 8h; the obtained reaction material was dispersed in 2mol / L HCl (100mL), extracted with EtOAc (3×30mL), combined organic layers, and washed with water and saturated saline respectively Washed, dried over anhydrous magnesium sulfate, filtered, and the filtrate was spin-dried to obtain a crude product. The crude product was separated by silica gel column chromatography (eluent: V 石油醚 :V 乙酸乙酯 =30:1 to 5:1), a white sol...

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 2

[0040]

[0041] Compound 1 (0.45 g, 0.66 mmol) was dissolved in MeOH, THF and H 2 Mixed solvent composed of O (9mL, MeOH, THF and H 2 The volume ratio of O is 1:1:1), add 2mol / L sodium hydroxide solution (0.5mL / 30min, 1.5mL, 3.0mmol) under ice-bath conditions, stir and react at room temperature for 12h; Adjust the pH to 2 with HCl, spin off MeOH and THF under reduced pressure; the resulting residue was dispersed in EtOAc (100 mL), washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried to obtain a crude product. The crude product was separated by silica gel column chromatography (eluent: V 石油醚 :V 乙酸乙酯 =3:1to 1:1), compound 2 (0.41 g, 94%, white solid) was obtained.

[0042] Yield: 0.41g, 94%, white solid; R f =0.29(Petroleum ether:EtOAc=1:1).m.p.108-110℃. 1 H NMR (500MHz, CDCl 3 ):δ0.62,0.76(2s,each 3H,2×CH 3 ),0.84(s,6H,2×CH 3 ),0.87,0.88,1.10(3s,each 3...

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PUM

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Abstract

The invention discloses a series of 28-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthesis methods and application thereof. The pentacyclic triterpene derivatives particularly comprises two 28-(L-phenylalanine)-oleanolic acid derivatives, two 28-(L-phenylalanine)-ursolic acid derivatives and two 28-(L-phenylalanine)-glycyrrhetinic acid derivatives. Shown by results of in vitro tests by the applicant, the derivatives have favorable proliferation inhibition activity to certain tumor cell strains, have better potential medicinal value, and are expected to be used for preparing various anti-tumor drugs.

Description

technical field [0001] The invention relates to pentacyclic triterpene derivatives, in particular to 28-(L-phenylalanine)-pentacyclic triterpene derivatives and a synthesis method and application thereof. Background technique [0002] Pentacyclic triterpenoids are widely distributed in nature and are the active ingredients of many commonly used Chinese herbal medicines. According to their alkane structure, they are mainly divided into: oleanane type, arbutane type, and lupine type, etc. Pentacyclic triterpenoids generally have a wide range of biological activities, such as lowering blood sugar and blood lipids, anti-inflammation, anti-tumor, anti-HIV, and anti-virus. Oleanolic acid has been on the market in China for nearly 40 years as a liver protection tablet. [0003] Amino acids, as the basic unit of biological functional macromolecular proteins, play an important role in the process of life. Tumor cells have a strong metabolism and need a large amount of nutrients to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P35/00
CPCA61P35/00C07J63/008
Inventor 程克光张琚政温小安刘春梅陈振锋
Owner GUANGXI NORMAL UNIV
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