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Nuciferine derivative and application of nuciferine derivative in preparation of uric acid reducing medicine

A technology of nuciferine and medicine, applied in the field of nuciferine derivatives and its application in the preparation of uric acid-lowering drugs, can solve problems such as mental confusion, hearing loss, coma, etc., and achieve excellent activity, high uric acid activity, The effect of strong uric acid activity

Pending Publication Date: 2022-05-31
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Common central nervous symptoms include drowsiness, trance, and depression. It has been reported that ibuprofen can cause aseptic meningitis and indomethacin can cause headache. Mental confusion occurs, overdose of aspirin can cause coma, aspirin can also cause tinnitus, hearing loss and other side effects
[0008] The lotus leaf is rich in sources and can be used for both medicine and food. Its main component is alkaloids. The extract of the lotus leaf has certain anti-inflammatory and uric acid-lowering activities, but it is inconvenient to use the lotus leaf directly, and the existing lotus leaf Alkaline activity is too low to be used directly, therefore, how to make better use of Nuciferine alkaloids, or to study new Nuciferine derivatives for anti-inflammation and lowering uric acid is very meaningful

Method used

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  • Nuciferine derivative and application of nuciferine derivative in preparation of uric acid reducing medicine
  • Nuciferine derivative and application of nuciferine derivative in preparation of uric acid reducing medicine
  • Nuciferine derivative and application of nuciferine derivative in preparation of uric acid reducing medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0327] Example 1 Synthesis of 1-Ethyl sulfone

[0328]Accurately weigh 2.81 g (10 mmol) of 1-O-desmethyl lotus leaf base, dissolve it in 50 mL of chloroform, place it in a nitrogen-filled three-necked flask, add it and dissolve it in 120 mL of piperidine under magnetic stirring, and control the temperature to 0-5 ℃ mixed for 1.0h, added 2.58g (about 12mmol) of ethylsulfonyl chloride dissolved in 100mL of chloroform, washed with 100mL of deionized water for 3-5 times after the reaction, and concentrated the organic phase to about 10mL by rotary evaporation. Alumina column separation and purification (eluent v / v: chloroform / methanol=150 / 1-100 / 1), collecting product fractions, steaming the solvent under reduced pressure to obtain the product, TLC tracking the reaction and the separation and purification process of the product, 2.26g of light green powder product was obtained, the melting point of the product was 87.0-88.7°C, 1 H NMR, 13 By C NMR and HR-MS analysis, it was det...

Embodiment 2

[0329] Example 2 Synthesis of 1-n-propanesulfonate-based susceptin

[0330] Accurately weigh 2.81 g (10 mmol) of 1-O-desmethyl succinate, dissolve it in 100 mL of dichloromethane and place it in a nitrogen-filled three-necked flask, add 5.06 g of triethylamine dissolved in 50 mL of dichloromethane under magnetic stirring (about 50 mmol), control the temperature to 0-5 °C and mix for 2.0 h, add 1.71 g (about 12 mmol) of n-propylsulfonyl chloride dissolved in 100 mL of dichloromethane, and wash with 100 mL of deionized water for 3-5 times after the reaction. The organic phase was concentrated to about 10 mL by rotary evaporation, separated and purified by a neutral alumina column (eluent v / v: dichloromethane / methanol=150 / 1-100 / 1), the product fractions were collected, and the solvent was evaporated under reduced pressure to obtain product, TLC followed the reaction and the separation and purification process of the product to obtain 2.89g of light yellow oily product. 1 H NM...

Embodiment 3

[0331] Example 3 Synthesis of 1-n-butanesulfonate susceptin

[0332] Accurately weigh 2.81 g (10 mmol) of 1-O-desmethyl succinate, dissolve it in 120 mL of tetrahydrofuran and place it in a nitrogen-filled three-necked flask, add γ-Al under mechanical stirring 2 O 3 -Na 5.60g, after mixing for 1.0h, add 3.13g (about 20mmol) of 1-n-butylsulfonyl chloride dissolved in 100mL of tetrahydrofuran, control the temperature to -20~-5℃ and react for about 10h, then add 3g of activated carbon after the reaction Mixed for 2 h, filtered, the filter cake was washed 2-3 times with 100 mL of tetrahydrofuran, the filtrate was collected, concentrated and evaporated to about 20 mL, crystallized at room temperature overnight, TLC followed the separation and purification process of the reaction and the product, filtered, and the solid was dried at 60 ° C for 4 h, 1.86g of pale green powder was obtained, the melting point of the product was 90.2-91.7°C, 1 H NMR, 13 By C NMR and HR-MS analysis...

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Abstract

The invention provides a nuciferine derivative and application of the nuciferine derivative in preparation of uric acid lowering drugs. The nuciferine derivative has a structure as shown in a formula I, has activity of inhibiting URAT1 expression, and can be used as a URAT1 inhibitor for reducing uric acid. Wherein R is selected from alkyl, cycloalkyl, aryl and heterocyclic radical; the alkyl group, the aryl group and the heterocyclic group are unsubstituted or substituted by one or more substituent groups selected from alkyl, alkoxy, halogen, cyano and nitryl; wherein the aryl is selected from phenyl, benzyl, naphthyl and biphenyl; the heterocyclic group is selected from thienyl, pyridyl, quinolyl, isoquinolyl and isoxazole; the alkyl is C1-C8 alkyl, and the naphthenic base is C3-C6 naphthenic base; the pharmaceutically acceptable salt is inorganic acid salt or organic acid salt of a compound shown as a formula I; wherein R is not bromomethyl, isopropyl, n-hexyl or n-octyl.

Description

technical field [0001] The application relates to the field of medicine, in particular to lotus leaf alkaloid derivatives and their application in the preparation of uric acid-lowering drugs. Background technique [0002] The information disclosed in this Background of the Invention is intended to enhance understanding of the general background of the invention and should not necessarily be taken as an acknowledgement or any form of suggestion that this information is already known as the prior art to a person of ordinary skill in the art. [0003] Inflammation is characterized by an influx of white blood cells, redness, warmth, swelling, pain, and dysfunction of the organs involved. Inflammation is generally divided into acute inflammation and chronic inflammation according to whether it is long-term or short-term in the human body. Acute inflammation is the rapid response of the human body to the invasion of harmful stimuli, which is achieved by the continuous flow of pla...

Claims

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Application Information

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IPC IPC(8): A61K31/473A61P3/06A61P3/10A61P19/06A23L33/105C07D221/18C07D401/12C07D409/12
CPCA61K31/473A61P3/06A61P3/10A61P19/06A23L33/105C07D221/18C07D401/12C07D409/12A23V2002/00A23V2200/30A23V2200/3262A23V2200/328A23V2250/21Y02P20/55
Inventor 刘玉法张玉凯刘超彭立增解慧敏
Owner SHANDONG NORMAL UNIV
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