L-phenylalanine modified maslinic acids as well as synthesis methods and application thereof

A synthesis method and technology of phenylalanine, applied in the field of maslinic acid derivatives, can solve the problems of undiscovered maslinic acid benzyl ester, etc., and achieve 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

However, no relevant reports on the activity of benzyl maslinate have been found so far
There are no relevant reports on the synthesis of maslinic acid derivatives modified by L-phenylalanine and their application in tumor therapy

Method used

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  • L-phenylalanine modified maslinic acids as well as synthesis methods and application thereof
  • L-phenylalanine modified maslinic acids as well as synthesis methods and application thereof
  • L-phenylalanine modified maslinic acids as well as synthesis methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of compound 1 and 2

[0036] Get benzyl maslinic acid (3.00g, 5.33mmol) and dissolve in CH 2 Cl 2 (50mL), sequentially added Boc-L-phenylalanine (3.50g, 13.33mmol), DCC (3.00g, 13.33mmol) and DMAP (0.16g, 1.33mmol), stirred at room temperature for 12h, the reaction solution was filtered and washed with CH 2 Cl 2 After washing, the filtrate was evaporated under reduced pressure to obtain a residue, and the residue was separated by silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =20:1 to 8:1), the combined fractions were detected by thin layer chromatography to obtain compound 1 (1.20g, 27.8%, white solid) and compound 2 (2.90g, 51.5%, white solid), respectively.

[0037] Compound 1

[0038]

[0039] Yield: 1.20g, 27.8%, white solid; R f =0.412 (Petroleum ether: EtOAc=5:1).m.p.96-98°C. 1 H NMR (400MHz, CDCl 3)6 (ppm): 0.58, 0.84, 0.90, 0.93, 0.96, 1.03, 1.11 (7s, each 3H, 7×CH 3 ), 1.41(s, 9H, 3×CH 3 Boc ), 0.71-2.05(m, 20H), 2.91...

Embodiment 2

[0042] Embodiment 2: the synthesis of compound 3

[0043]

[0044] 1 (0.50g, 0.62mmol) was dissolved in methanol (30mL), ammonium formate (0.39g, 6.20mmol) and 10% Pd / C (0.05g) were added successively, and reacted at 55°C for 1h. Cool to room temperature, filter, the filter cake is washed with methanol, and the filtrate is evaporated to remove the solvent to obtain a residue, which is obtained by H 2 O and CH 2 Cl 2 The mixed solvent (60mL, H 2 O and CH 2 Cl 2 The volume ratio is 1:1) Shake well to separate the liquid, and use CH for the water phase 2 Cl 2 (2 × 30mL) extraction; the combined organic phases were washed with water and saturated brine respectively, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated to obtain a residue; the residue was separated by silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =15:1 to3:1), to obtain compound 3 (0.40g, 89.5%, white solid).

[0045] Yield: 0.40g, 89.5%, white solid; R f =0.432(Petroleum eth...

Embodiment 3

[0046] Embodiment 3: the synthesis of compound 3

[0047] Repeat embodiment 2, difference is: replace methyl alcohol with THF, the mixed solvent that liquid separation is used changes into by H 2 The composition of O and EtOAc was 1:2; the reaction was carried out at 10°C, the reaction time was controlled at 10 h, and the rest remained unchanged. Finally a white solid (0.34 g, 75.8%) was obtained.

[0048] The obtained product was characterized by H NMR spectroscopy and identified as compound 3.

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Abstract

The invention discloses a series of L-phenylalanine modified maslinic acids as well as synthesis methods and application thereof. The L-phenylalanine modified maslinic acids are particularly 8 compounds. Benzyl maslinate and Boc (Butyloxycarbonyl)-L-phenylalanine firstly react in a first organic solvent in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine; reactants are subjected to silica gel column chromatography after the solvent is recovered, so as to obtain a compound 1 and a compound 2; and then, the compound 1 and the compound 2 which serve as raw materials react respectively to obtain the rest 6 compounds. 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 maslinic acid derivatives, in particular to L-phenylalanine modified maslinic acid and its synthesis method and application. Background technique [0002] Maslinic acid is a pentacyclic triterpene acid, which exists in many natural plants, especially hawthorn, red dates, loquat leaves and olives, and has high safety to human body. In recent years, it has been found that maslinic acid has various biological activities such as anti-cancer, anti-oxidation, anti-AIDS, anti-bacteria, and anti-diabetes. However, no relevant reports on the activity of benzyl maslinate have been found so far. [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 maintain the state of rapid cell proliferation, among which amino acids are essential nutrients. L-phenylalanine is an essential ami...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P35/00
CPCA61P35/00C07J63/008
Inventor 程克光孙立温小安刘春梅陈振锋
Owner GUANGXI NORMAL UNIV
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