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Compound with chemical kinetics effect and preparation method of nano vesicle

A chemical kinetics and compound technology, applied in the field of tumor treatment, to achieve good therapeutic effect and reduce acidity

Inactive Publication Date: 2021-09-21
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, most of the reported CDT or GOx combined CDT systems are constructed of iron or other transition metal-based inorganic or metal-organic framework nanomaterials, while other kinds of nanoparticles, such as liposome nanoparticles, polymer nanoparticles and supramolecular nanoparticles are difficult to use in CDT

Method used

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  • Compound with chemical kinetics effect and preparation method of nano vesicle
  • Compound with chemical kinetics effect and preparation method of nano vesicle
  • Compound with chemical kinetics effect and preparation method of nano vesicle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Intermediate 4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1Hpyrano[3',4':6,7]indolo[1- 2,b] Synthesis of quinolin-4-yl (2-((2-(prop-2-yn-1 oxy)ethyl)disulfanyl)ethyl)carbonate.

[0027] Under nitrogen, triphosgene (237 mg, 0.8 mmol) and DMAP (1.075 g, 8.0 mmol) were added to 100 mL of anhydrous chloroform, and the mixture was stirred at room temperature for 0.5 h. Then camptothecin (696 mg, 2.0 mmol) was continuously added to the reaction mixture in three batches within 2 hours at room temperature, and finally 2-((2-(2--2-propan-2-propoxy) Ethyl)disulfanyl)ethan-1-ol (0.5 g, 2.6 mmol) in anhydrous chloroform. The resulting mixture was stirred at room temperature for an additional 12 hours. After removing the solvent under reduced pressure, the crude product was purified by column chromatography using dichloromethane / methanol (v / v, 100:1) as eluent to afford intermediate 4-ethyl-3 as a pale yellow solid, 14-dioxo-3,4,12,14-tetrahydro-1H pyrano[3',4':6,7]indolo[1-2,b]qu...

Embodiment 2

[0031] (1) Synthesis of intermediate: with embodiment 1.

[0032] (2) Synthesis of camptothecin prodrugs with chemokinetic effects: using a mixture of dichloromethane / MeOH (1:2, v / v, 30mL) as the reaction medium, TBTA and Cu(CNCH 3 )4PF 6 As a catalyst, 4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1Hpyrano[3',4':6,7]indolo[1-2, b] quinoline-4-yl (2-(carbonic acid (2-(prop-2-yn-1oxy)ethyl)disulfanyl)ethyl)carbonate and (2-(6-azido Hexyloxy)oxy)methyl]cyclopent-2,4-dien-1-yl)(cyclopent-2,4-dien-1-yl)iron in a molar ratio of 1:3 at room temperature for 12 Hour. After removing the solvent under reduced pressure, the crude product was purified by column chromatography (dichloromethane / methanol 100 / 1) to obtain a light yellow solid, which was the target product cyclopenta-2,4-dien-1-yl (2- (6-(4-(2-(2-(4-Ethyl-3,14-dioxo3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7 ]indolo[1,2-b]quinolin-4yl)oxy)carbonyl)oxy)ethyl)disulfanyl)ethoxy)methyl)-1H-1,23-triazole 1 -yl)hexyloxy)methyl)cyclopen...

Embodiment 3

[0035] (1) Synthesis of intermediate: with embodiment 1.

[0036] (2) Synthesis of camptothecin prodrugs with chemokinetic effects: using a mixture of dichloromethane / MeOH (1:2, v / v, 30mL) as the reaction medium, TBTA and Cu(CNCH 3 )4PF 6 As a catalyst, 4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1Hpyrano[3',4':6,7]indolo[1-2, b] quinoline-4-yl (2-(carbonic acid (2-(prop-2-yn-1oxy)ethyl)disulfanyl)ethyl)carbonate and (2-(6-azido Hexyloxy)oxy)methyl]cyclopent-2,4-dien-1 base)(cyclopent-2,4-dien-1-yl)iron in a molar ratio of 1:5 at room temperature for 12 Hour. After removing the solvent under reduced pressure, the crude product was purified by column chromatography (dichloromethane / methanol 100 / 1) to obtain a light yellow solid, which was the target product cyclopenta-2,4-dien-1-yl (2- (6-(4-(2-(2-(4-Ethyl-3,14-dioxo3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7 ]indolo[1,2-b]quinolin-4yl)oxy)carbonyl)oxy)ethyl)disulfanyl)ethoxy)methyl)-1H-1,23-triazole 1 -yl)hexyloxy)methyl)cyclop...

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Abstract

The invention discloses a preparation method of a compound with chemical kinetics effect and a nano vesicle. The synthesis method of the compound is as follows: a mixture of dichloromethane / MeOH (1: 2, v / v, 30mL) is taken as a reaction medium, TBTA and Cu(CNCH3)4PF6 are taken as catalysts, 4-ethyl-3, 14-dioxo-3, 4, 12, 14-tetrahydro-1H-pyrano[3', 4': 6, 7]indolo[1-2, b]quinoline-4-yl (2-(carbonic acid(2-(propyl-2-alkyn-1-oxyl) ethyl) dithioalkyl)ethyl)carbonate and (2-(6-azidohexyloxy) oxyl) methyl)cyclopent-2,4-dien-1-yl)(cyclopent-2,4-dien-1-yl) iron are stirred for 12 hours at the room temperature according to the molar ratio of 1: 1. And after removing the solvent under reduced pressure, the crude product is purified through column chromatography (dichloromethane / methanol = 100 / 1) to obtain a light yellow solid, namely the target product. The compound camptothecin prodrug provided by the invention can reduce the acidity in tumors and increase the content of H2O2.

Description

technical field [0001] The invention relates to the technical field of tumor treatment, in particular to a compound with chemical kinetic effect and a preparation method of nanovesicles. Background technique [0002] Clinically, chemotherapy, photodynamic therapy, radiotherapy and surgery have been used as the main methods to inhibit tumor proliferation. However, these approaches have only achieved limited therapeutic efficacy due to the inherent therapeutic resistance, heterogeneity, and metastatic nature of these tumors. In recent years, chemodynamic therapy (CDT) has received a lot of attention, which utilizes iron-mediated Fenton or Fenton-like reactions to drive intratumoral or intracellular H 2 o 2 It is transformed into hydroxyl radicals (OH) to increase the level of oxidative stress in cells, thereby producing a killing effect on tumors. And due to the short half-life and high oxidative capacity, the generated OH only effectively damages the generation site, there...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02A61K9/127A61K38/44A61P35/00
CPCC07F17/02A61K9/127A61K38/443A61P35/00C12Y101/03004A61K2300/00
Inventor 刘昕刘季孟迟钱建强凌诗佳凌勇
Owner NANTONG UNIVERSITY
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