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Lupeol pyridine quaternary ammonium salt derivative, preparation method and application thereof

A technology of pyridine and quaternary ammonium salts of soy alcohol is applied in the field of lupin alcohol pyridine quaternary ammonium salt derivatives and their preparation, which can solve the problems of limited anti-tumor research, unsatisfactory dissolution effect, easy precipitation of drug crystals, and the like, and achieves significant inhibition of effect, obvious anti-cancer effect, significant R&D potential effect

Active Publication Date: 2020-09-08
广州市番禺区中心医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, lupeol is insoluble in water, although it can be miscible with ether, benzene, petroleum ether and hot ethanol, but the solubility is not good
In research experiments, warm absolute ethanol and dimethyl sulfoxide (DMSO) are often used as a solvent mixed in a ratio of 1:1, but the dissolution effect is still not ideal, and drug crystals are easily precipitated, which limits its anti-tumor effect. research, hindering its development to clinical use

Method used

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  • Lupeol pyridine quaternary ammonium salt derivative, preparation method and application thereof
  • Lupeol pyridine quaternary ammonium salt derivative, preparation method and application thereof
  • Lupeol pyridine quaternary ammonium salt derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Preparation of compound A (lupeyl alcohol pyridinium quaternary ammonium salt derivative):

[0040]

[0041] Compound 1 (1.28g, 3.0mmol) was dissolved in 30mL of dichloromethane (DCM), compound 2 (0.53g, 3.3mmol) was added, and reacted at room temperature for 2h. TLC monitored that compound 1 was completely reacted. Add 30 mL of dichloromethane to dilute the reaction solution, wash twice with saturated brine, 30 mL each time, dry the organic phase with anhydrous sodium sulfate, filter, and concentrate the filtrate to dryness to obtain 1.42 g of crude compound 3, which was not further processed. purified and used directly in the next step.

[0042] The crude compound 3 was dissolved in 30 mL of dichloromethane, compound 4 (0.39 g, 3.6 mmol) was added thereto, and the reaction was stirred at 40 degrees for 17 h. After the reaction was completed, cool to room temperature, add 30 mL of dichloromethane to dilute the reaction solution, wash twice with satura...

Embodiment 2

[0046] Example 2 Compound A of the present invention inhibits human tumor cell proliferation test

[0047] 1. Drug dissolution: lupeol was dissolved in warm absolute ethanol and DMSO at a ratio of 1:1 to prepare a total solution of 7811.57 μM; compound A of the present invention was dissolved in DMSO to prepare a total solution of 14228.6 μM. Dilute with complete medium to the corresponding working concentration for experiments.

[0048] 2. Cell culture: 16 kinds of tumor cell lines used in the experiment (bladder cancer 5637 cells, kidney cancer 786-O cells, neuroblastoma SK-N-SH cells, liver cancer Huh7 cells, nasopharyngeal carcinoma Cne2 cells, prostate cancer PC3 cells , colon cancer Colo205 cells, colon cancer DLD-1 cells, colon cancer HCT-116 cells, colon cancer HT-29 cells, colon cancer Lovo cells, colon cancer RKO cells, colon cancer SW480 cells, colon cancer SW620 cells, colon cancer Caco2 cells, colon cancer THC-8307 cells; 16 kinds of cell lines are conventional c...

Embodiment 3

[0057] Example 3 The toxicity test of compound A of the present invention to normal human epithelial cells

[0058] 1. Drug dissolution: the compound A of the present invention was dissolved in DMSO, prepared into a total solution of 14228.6 μM, and diluted with complete medium to the corresponding working concentration for experiments.

[0059] 2. Cell culture: human prostate epithelial RWPE-1 cells, liver HL-7702 cells, colonic epithelial HCoEpiC cells, nasopharyngeal epithelial NP69 cells, breast epithelial MCF-10A cells and alveolar epithelial HPAEpiC cells and other 6 strains of normal epithelial cells (all were Conventional commercially available cell lines) were placed in the corresponding medium containing 10% fetal bovine serum (FBS) or without FBS, and kept at 37°C, saturated humidity, and a volume fraction of 5% CO 2 Cultured in an incubator, the corresponding media for various cells are shown in Table 3.

[0060] Table 3 The culture medium of each normal cell

[...

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Abstract

The invention discloses a lupeol pyridine quaternary ammonium salt derivative, a preparation method and application thereof, belongs to the field of drug synthesis, and provides a lupeol pyridine quaternary ammonium salt derivative and application in treatment and / or prevention of cancer, wherein the molecular formula of the lupeol pyridine quaternary ammonium salt derivative is C38H59IN2O2, and the molecular weight of the lupeol pyridine quaternary ammonium salt derivative is 702.1. According to the invention, a water-soluble lupeol pyridine quaternary ammonium salt derivative is synthesizedby using lupeol as an initial raw material, and pharmacological experiments prove that the derivative has a remarkable inhibition effect on various tumor cell strains, has an obvious anti-cancer effect compared with lupeol, has a low toxic effect on normal cell strains, is good in hydrophilicity, is easily dissolved in solvents such as water, ethanol, DMSO and the like, and has solubility superiorto that of lupeol, so that the derivative has great research and development potential; and the lupeol pyridine quaternary ammonium salt derivative is expected to be developed into an anti-tumor drugand has certain medical value and market prospect.

Description

technical field [0001] The invention belongs to the field of drug synthesis and relates to a lupeyl alcohol pyridinium quaternary ammonium salt derivative and a preparation method and application thereof. Background technique [0002] Cancer, that is, malignant tumor, is a major disease that endangers human health and is caused by multiple gene mutations, multiple factors, and multi-stage development. According to the latest data, there were 18,078,957 new cancer cases and 9,555,027 cancer deaths worldwide in 2018. Therefore, actively carry out various work on the prevention and treatment of cancer, how to effectively treat cancer has become a top priority. The treatment methods for malignant tumors mainly include surgery, radiotherapy, chemotherapy, and biological therapy. Chemotherapy is still one of the main means of treating tumors at present and for a long time in the future. Quality of Life. In the face of today's many tumor diseases, the existing anti-tumor drugs a...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/58A61P35/00
CPCA61P35/00C07J63/008
Inventor 韩泽平何金花黎毓光
Owner 广州市番禺区中心医院
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