Nuciferine derivative as well as preparation method and application thereof

A lotus leaf alkaloid derivative, the technology of lotus leaf alkaloid, which is applied in the field of medicine, can solve the problems of weak lipid-lowering activity and the like, and achieves the improvement of adsorption capacity, increased hypoglycemic and lipid-lowering activities, and good hypoglycemic and lipid-lowering activities. Effect

Pending Publication Date: 2022-05-20
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The lipid-lowering activity of existing nuciferine and its derivatives is no...

Method used

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  • Nuciferine derivative as well as preparation method and application thereof
  • Nuciferine derivative as well as preparation method and application thereof
  • Nuciferine derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0227] Example 1 Synthesis of 1-O-benzylnuciline

[0228] Accurately weigh 2.81g (10mmol) of 1-O-desmethylnuciferine, dissolve it in 50mL of dichloromethane solvent and place it in a 250mL three-necked flask filled with nitrogen, add 0.29g (about 12mmol) of sodium hydride, and mechanically Stir and mix for 2.0 hours, place in a cold trap, add 1.27g (about 10mmol) benzyl chloride dissolved in 30mL of dichloromethane, and control the temperature at -20~-10°C to react until 1-O-desmethyl nuciferine reacts Complete, add 60mL of deionized ice water after the reaction, separate the organic phase, use dichloromethane for the water phase 3 times (for example, 50mL×3), combine the organic phase, evaporate the organic phase to obtain 2.21g of light yellow powder product, TLC Tracking the reaction and the separation and purification process of the product, the melting point of the product is 103.5-105.2 ° C, after 1 H NMR, 13 C NMR and HR-MS analysis, determined to be 1-O-benzylnucif...

Embodiment 2

[0229] Example 2 Synthesis of 1-O-O-Fluorobenzyl Nuciferine

[0230] Accurately weigh 2.81g (10mmol) of 1-O-desmethylnuciferine, dissolve it in 30mL of DMF solvent and place it in a 250mL three-necked flask filled with nitrogen, add 0.56g (about 10mmol) of potassium hydroxide, and mechanically stir at room temperature Mix for 2.0 hours, add 2.89g (about 20mmol) o-fluorobenzyl chloride dissolved in 50mL DMF, react at 30-40°C until the reaction of 1-O-desmethylnuciferine is complete, and use 60mL deionized ice Wash 3-5 times with water, concentrate the organic phase to about 10 mL by rotary evaporation, separate and purify through a neutral alumina column (eluent v / v: dichloromethane / methanol=200 / 1-100 / 1), and collect product fractions , The solvent was distilled off under reduced pressure to obtain the product, TLC traced the separation and purification process of the reaction and the product, and obtained 2.44 g of a light green powdery product. The melting point of the pro...

Embodiment 3

[0231] Example 3 Synthesis of 1-O-m-fluorobenzylnuciferine

[0232] Accurately weigh 2.81g (10mmol) of 1-O-desmethylnuciferine, dissolve it in 30mL DMF solvent and place it in a 250mL three-necked flask filled with nitrogen, add 3.41g (about 40mmol) of piperidine, and mix mechanically at room temperature 2.0h, add 2.17g (about 15mmol) m-fluorobenzyl chloride dissolved in 50mL DMF, react at 90-100°C until the reaction of 1-O-desmethylnuciferine is complete, wash with 60mL deionized ice water after the reaction 3-5 times, the organic phase was concentrated by rotary evaporation to about 20mL, crystallized at room temperature for 4-6h, filtered with suction, and the solid was dried at 60°C for 4-6h to obtain the product. TLC traced the separation and purification process of the reaction and the product to obtain 2.03 g of light green powdery product, the melting point of the product is 102.7-104.5 ° C, after 1 H NMR, 13 According to C NMR and HR-MS analysis, it was determine...

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Abstract

The invention relates to the field of medicines, in particular to a nuciferine derivative and a preparation method and application thereof. The nuciferine derivative disclosed by the invention has a structure as shown in a formula (I), wherein R is substituted benzyl or substituted pyridyl; the substituted benzyl is substituted by one or more substituent groups selected from halogen, alkyl, alkoxy, halogenated alkyl, nitro and cyano; the substituted pyridyl is selected to be substituted by alkyl; the salt is formed by the compound with the structural formula and organic acid or inorganic acid. The compound can be used as an alpha-glycosidase inhibitor and/or a bile acid chelating agent due to the structural characteristics of alkaloid and aromatic hydrocarbon containing heteroatoms, has good hypoglycemic and lipid-lowering activity, and can be applied to treatment and improvement of hyperglycemia or hyperlipidemia and the like.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a nuciferine derivative and a preparation method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily regarded as an acknowledgment or any form of suggestion that the information has become the prior art known to those skilled in the art. [0003] Diabetes is a common chronic disease caused by endocrine and metabolic disorders, manifested as hyperglycemia, metabolic disorders of fat and protein, and accompanied by symptoms such as insufficient insulin secretion or insulin resistance. The clinical manifestations are: three more and one less (ie: polydipsia, polyphagia, polyuria, fatigue, weight loss). Prolonged illness can cause damage to the system, leading to chronic progressive diseases (complications) of kidney...

Claims

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Application Information

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IPC IPC(8): C07D221/18A61K31/473A61P3/06A61P3/10A23L33/10
CPCC07D221/18A61P3/06A61P3/10A23L33/10A23V2002/00A23V2200/328A23V2200/3262Y02P20/55
Inventor 刘玉法张玉凯孙彬陈冬梅彭立增
Owner SHANDONG NORMAL UNIV
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