3-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthetic method and application thereof

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

Inactive Publication Date: 2019-03-22
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 3-(L-phenylalanine)

Method used

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  • 3-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthetic method and application thereof
  • 3-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthetic method and application thereof
  • 3-(L-phenylalanine)-pentacyclic triterpene derivatives as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of compound 1

[0026]

[0027] Get oleanolic acid (2.00g, 4.38mmol) and Boc-L-phenylalanine (1.74g, 6.57mmol) and dissolve in CH 2 Cl 2 (50mL), DCC (1.80g, 8.77mmol) and DMAP (0.10g, 0.87mmol) were added successively, stirred and reacted for 24h at room temperature, the obtained reaction material was filtered, the filter cake was washed with dichloromethane (20mL), and the filtrate was collected , spin-dried under reduced pressure, the obtained residue was dispersed in EtOAc (200 mL), washed with water and saturated brine successively, 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 =8:1-5:1), to obtain compound 1 (1.98g, 64.0%, white solid).

[0028] Yield: 1.98g, 64.0%, white solid; R f =0.72(Petroleum ether:EtOAc=2:1).m.p.116-118℃. 1 H NMR (500MHz, CDCl 3 ):δ0.73(s,3H,CH 3 ),0.79(s...

Embodiment 2

[0029] Embodiment 2: the synthesis of compound 1

[0030] Take oleanolic acid (2.00g, 4.38mmol) and Boc-L-phenylalanine (1.74g, 6.57mmol) and dissolve in MeOH (50mL), add DCC (1.80g, 8.77mmol), DMAP (0.10 g, 0.87mmol), stirring and reacting at room temperature for 10h, the resulting reaction material was filtered, the filter cake was washed with MeOH (20mL), the filtrate was collected, spin-dried under reduced pressure, and the resulting residue was separated by silica gel column chromatography (eluent: V 石油醚 :V 乙酸乙酯 =8:1-5:1), a white solid (1.21 g, 40.0%) was obtained.

[0031] The obtained product was characterized by H NMR spectrum and identified as compound 1.

Embodiment 3

[0032] Embodiment 3: the synthesis of compound 2

[0033]

[0034] Take compound 1 (0.20g, 0.28mmol) and dissolve in CH2 Cl 2 (15mL), add TFA (0.6mL, 0.2mL / 1h), stir the reaction at room temperature for 3h, add saturated aqueous sodium bicarbonate solution dropwise to the material obtained in the reaction until no bubbles are generated, and use CH 2 Cl 2 (3×50 mL), combined the organic layers, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried to obtain the crude product. The crude product was separated by silica gel column chromatography (eluent: V 石油醚 :V 乙酸乙酯 =3:1-1:1), to obtain compound 2 (0.11 g, 64.0%, white solid).

[0035] Yield: 0.11g, 64.0%, white solid; R f =0.31(Petroleum ether:EtOAc=1:1).m.p.144-146℃. 1 H NMR (400MHz, CDCl 3 ):δ0.74,0.80,0.82,0.89,0.921,0.926,1.12(7s,each 3H,7×CH 3 ),0.84-2.00(m,22H),2.79-2.86(m,2H,H-18,phCH),3.14(dd,J=5.4,13.6Hz,1H,phCH),3.74-3.77(m,1H, NCHCOO), 4.50-4.54(m, 1H,...

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Abstract

The invention discloses a series of 3-(L-phenylalanine)-pentacyclic triterpene derivatives as well as a synthetic method and an application thereof. The pentacyclic triterpene derivatives comprise two3-(L-phenylalanine)-oleanolic acid derivatives and two 3-(L-phenylalanine)-glycyrrhetinic acid derivatives, specially, one 3-(L-phenylalanine)-oleanolic acid derivative or one 3-(L-phenylalanine)-glycyrrhetinic acid derivative is obtained from oleanolic acid/glycyrrhetinic acid, Boc-L-phenylalanine, dicyclohexylcarbodiimide and 4-dimethylaminopyridine by a reaction and subjected to a reaction with trifluoroacetic acid, and the other two derivatives are obtained. In-vitro test results prove that the 3-(L-phenylalanine)-pentacyclic triterpene derivatives have good proliferation inhibition activity on certain tumor cell lines, have better potential medicinal values and are expected to be applied to preparation of various antitumor drugs.

Description

technical field [0001] The invention relates to pentacyclic triterpene derivatives, in particular to 3-(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 m...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P35/00A61K31/56
CPCA61P35/00C07J63/008
Inventor 程克光刘春梅温小安张琚政陈振锋
Owner GUANGXI NORMAL UNIV
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