Synthesis method of nuciferine or derivative thereof, nuciferine derivative and application of nuciferine derivative

A technology of a lotus alkaloid derivative and a synthesis method, which is applied in the directions of drug combination, organic chemistry, metabolic diseases, etc., can solve the problems such as no effective chemical synthesis method of lotus alkaloid or its derivatives, and achieves simple, efficient and easy synthesis steps. Obtain, respond efficiently

Pending Publication Date: 2022-07-15
HUAQIAO UNIVERSITY +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is currently no effective chemical synthesis method for nuciferine or its derivatives in the art

Method used

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  • Synthesis method of nuciferine or derivative thereof, nuciferine derivative and application of nuciferine derivative
  • Synthesis method of nuciferine or derivative thereof, nuciferine derivative and application of nuciferine derivative
  • Synthesis method of nuciferine or derivative thereof, nuciferine derivative and application of nuciferine derivative

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preparation example Construction

[0061] The invention provides a kind of synthetic method of lotus leaf base or its derivative, comprising the following steps:

[0062] (1) the compound with the structure shown in formula IV, R-X and the basic catalyst are mixed to carry out the Schotten-Baumann reaction to obtain the compound with the structure shown in formula V; in the R-X, R is an aliphatic hydrocarbon group, an aromatic hydrocarbon group or a Acyl, X is halogen;

[0063]

[0064] (2) mixing the compound with the structure shown in formula V, the phosphine ligand compound, the basic reagent and the catalyst to carry out a carbon-hydrogen bond activation reaction to obtain lotus leaf base or its derivative;

[0065] Said lotus leaf base or its derivative has the structure shown in formula VI:

[0066]

[0067] When R is a methyl group, the compound of the structure shown in formula VI is salicylic acid, and when R is another group, the compound of the structure shown in formula VI is a salicylic aci...

Embodiment 1

[0122] Network Pharmacology and Molecular Docking Technology

[0123] 1. Materials and methods

[0124] Screening of drug components and targets: TCMSP (Traditional Chinese Medicine System Pharmacology Database and Analysis Platform) software systematically analyzes pharmacokinetics, pharmacodynamics, omics, etc. Provides a platform for pharmacology and validation studies. At the same time, it also provides new research methods for target discovery and new drug development. The invention retrieves the chemical constituents of lotus leaves according to the inclusion of the TCMSP database, a unique system pharmacology platform of traditional Chinese medicine. Taking the two conditions of oral bioavailability (OB) ≥ 30% and drug-likeness (DL) ≥ 0.18 as the thresholds, the corresponding compounds and corresponding targets were screened out. The main steps are as follows:

[0125] Target acquisition of disease-related effects: The following databases were searched and screened ...

Embodiment 2

[0152] Preparation of benzoyl salicylate (referred to as compound 6a)

[0153] The synthetic route of described benzoyl lotus leaf base is as shown in formula 1:

[0154]

[0155] At 0 °C, oxalyl chloride (30 mmol, 2.54 mL) was added to 2-bromophenylacetic acid (30 mmol, 6.45 g) dissolved in DCM (30 mL), then 0.6 g of DMF was added, and the reaction was performed at 30 °C for 2 h. After completion, rotary evaporation was carried out at 35°C to obtain compound 1 (10.3 g, 92%).

[0156] 3,4-Dimethoxyphenethylamine (30 mmol, 5.06 mL) and triethylamine (33 mmol, 4.58 mL) were dissolved in DCM (40 mL), then compound 1 (20 mmol, 10 g) was added at 0°C, The reaction was carried out at 35°C for 12h. After the reaction was completed, the reaction was quenched with 40 mL of brine, and then extracted with 100 mL of DCM. After drying with 10 g of anhydrous sodium sulfate, the anhydrous sodium sulfate was removed by filtration, and then rotary-evaporated at 35 °C to obtain compound 2 ...

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Abstract

The invention relates to the technical field of medicine synthesis, and provides a synthetic method of nuciferine or a derivative thereof, the nuciferine derivative and application of the nuciferine derivative. The preparation method comprises the following steps: carrying out Schotan-Baumann reaction on a compound with a structure as shown in a formula IV and R-X, and then activating through a carbon-hydrogen bond to obtain nuciferine or a derivative thereof. Furthermore, the compound with the structure shown in the formula IV is obtained by taking 2-bromophenylacetic acid as an initiator and carrying out acylating chlorination reaction, nucleophilic substitution reaction, Bischler-Napieralski reaction and reduction reaction. The synthesis method provided by the invention has the advantages of simple steps and easily available raw materials, and the carbon-hydrogen bond activation method is efficient, direct and flexible, and is very suitable for synthesis of nuciferine molecules. The nuciferine can be synthesized, and the nuciferine can be flexibly subjected to structural modification, so that a series of nuciferine derivatives are obtained, and a solid foundation is provided for developing nuciferine drugs for treating obesity and hyperlipidemia.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a method for synthesizing lotus alkaloid or a derivative thereof, and a lilac alkaloid derivative and application thereof. Background technique [0002] Obesity is a metabolic syndrome caused by the accumulation of fat and the destruction of the balance of energy metabolism due to excessive intake of energy by the body. Characterized by multiple deposits. The pathogenic factors of obesity are complex, including behavioral, environmental, physiological, genetic, social and economic factors. In recent years, the incidence of obesity has been increasing year by year worldwide, and it has become a worldwide health problem. [0003] Lotus leaf is the leaf of the Nymphaeaceae (Nymphaeaceae) plant of the genus Nelumbo. There are two kinds of plants in this genus, one is the American yellow lotus (Nelumbo pentapetala Fernald.), which is distributed in North America centered on t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C07D217/18A61P3/06A61P3/04
CPCC07D221/18C07D217/18A61P3/06A61P3/04
Inventor 汤须崇赵应伟李萱曹丽平
Owner HUAQIAO UNIVERSITY
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