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Synthesis method of beta-cyclodextrin derivative

A synthesis method and β-cyclodextrin technology are applied in the directions of drug combinations, pharmaceutical formulations, and non-active ingredients medical preparations, etc., which can solve the problems of complex synthesis methods and low product recovery rate, and achieve improved targeting ability, production and production efficiency. high rate effect

Inactive Publication Date: 2018-04-03
FOSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthetic method is complicated and the product recovery rate is low

Method used

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  • Synthesis method of beta-cyclodextrin derivative
  • Synthesis method of beta-cyclodextrin derivative
  • Synthesis method of beta-cyclodextrin derivative

Examples

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Comparison scheme
Effect test

Embodiment 1

[0029] A method for synthesizing beta cyclodextrin derivatives, comprising the following steps:

[0030] 1) In DMF, in Et 3 In the presence of N, CuI and ascorbic acid, 6A,6D-dideoxydiazidocyclodextrin (1) was combined with 1-O-(2-propargyl)-β under nitrogen protection at a temperature of 25°C. -D-lactoside undergoes a linking reaction for 15h to obtain a mixed mixture 2 containing two isomers 2-1 and 2-2; wherein 6A, 6D-dideoxydiazide cyclodextrin, 1-O-( 2-Propargyl)-β-D-lactoside, Et 3 The mass ratio of N, CuI and ascorbic acid is 1:1:0.08:0.08:0.08; the yield of mixture 2 is 78%;

[0031] 2) In DMF, under nitrogen protection, at a temperature of 25°C, at Et 3 In the presence of N, CuI and ascorbic acid, mixture 2 was reacted with 1-O-2-propargyl-β-D-galactoside for 10 h to obtain mixed β containing two isomers 3-1 and 3-2 Cyclodextrin derivative 3, wherein mixture 2, 1-O-2-propargyl-β-D-galactoside, Et 3 The mass ratio of N, CuI and ascorbic acid was 1:1.5:0.08:0.08:0....

Embodiment 2

[0037] A method for synthesizing beta cyclodextrin derivatives, comprising the following steps:

[0038] 1) In DMF, in Et 3 In the presence of N, CuI and ascorbic acid, 6A,6D-dideoxydiazidocyclodextrin (1) was combined with 1-O-(2-propargyl)-β under nitrogen protection at a temperature of 26°C. -D-lactoside undergoes a chain reaction for 12h to obtain a mixed mixture 2 containing two isomers 2-1 and 2-2; wherein 6A, 6D-dideoxydiazide cyclodextrin, 1-O-( 2-Propargyl)-β-D-lactoside, Et3 The mass ratio of N, CuI and ascorbic acid is 1:1:0.1:0.08:0.12; the yield of mixture 2 is 80%;

[0039] 2) In DMF, under nitrogen protection, at a temperature of 28°C, at Et 3 In the presence of N, CuI and ascorbic acid, mixture 2 was reacted with 1-O-2-propargyl-β-D-galactoside for 12 h to obtain a mixed β containing two isomers 3-1 and 3-2 Cyclodextrin derivative 3, wherein mixture 2, 1-O-2-propargyl-β-D-galactoside, Et 3 The mass ratio of N, CuI and ascorbic acid was 1:1.5:0.1:0.08:0.1. ...

Embodiment 3

[0045] A method for synthesizing beta cyclodextrin derivatives, comprising the following steps:

[0046] 1) In DMF, in Et 3 In the presence of N, CuI and ascorbic acid, 6A,6D-dideoxydiazidocyclodextrin (1) was combined with 1-O-(2-propargyl)-β under nitrogen protection at a temperature of 30 °C -D-lactoside undergoes a chain reaction for 12h to obtain a mixed mixture 2 containing two isomers 2-1 and 2-2; wherein 6A, 6D-dideoxydiazide cyclodextrin, 1-O-( 2-Propargyl)-β-D-lactoside, Et 3 The mass ratio of N, CuI and ascorbic acid is 1:1.2:0.1:0.1:0.1; the yield of mixture 2 is 85%;

[0047] 2) In DMF, under nitrogen protection, at a temperature of 30°C, at Et 3 In the presence of N, CuI and ascorbic acid, mixture 2 was reacted with 1-O-2-propargyl-β-D-galactoside for 12 h to obtain a mixed β containing two isomers 3-1 and 3-2 Cyclodextrin derivative 3, wherein mixture 2, 1-O-2-propargyl-β-D-galactoside, Et 3 The mass ratio of N, CuI and ascorbic acid was 1:2:0.12:0.1:0.1. ...

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Abstract

The invention discloses a synthesis method of a beta-cyclodextrin derivative. The synthesis method comprises the following steps: in DMF, in the presence of Et3N, CuI and ascorbic acid, carrying a linkage reaction among 6A,6D-dideoxydiazidocyclodextrin and 1-O-(2-propargyl)-beta-D-lactoside, then carrying out a reaction with 1-O-2-propargyl-beta-D-galactoside to obtain a mixed galactosyl and lactosyl modified beta-cyclodextrin derivative. The synthesis method is simple and easy to operate; by the synthesis method, the yield is high; when the beta-cyclodextrin derivative is used as a medicine carrier, the targeting ability, the solubility and the stability of a liver cancer medicine can be improved. The invention further provides a synthesis method of the 6A,6D-dideoxydiazidocyclodextrin, by which the defects that in the prior art, the synthesis method of the 6A,6D-dideoxydiazidocyclodextrin is complex, the yield is low and spectral characterization is not satisfactory are overcome.

Description

technical field [0001] The present invention relates to a method for synthesizing carbohydrate-conjugated 6A, 6D-difunctionalized beta-cyclodextrin derivatives, in particular to a method for synthesizing beta-cyclodextrin modified by galactosyl and lactosyl groups. Background technique [0002] Currently, during chemotherapy, there is a problem of non-specific tumor targeting in tumor therapy, which is caused by poor patient response to chemotherapy regimens and severe systemic toxicity. The main reasons for this result are due to the low therapeutic index of these drugs and also due to the low bioavailability of the drugs within tumor cells. Therefore, there is a need to find the ability to increase tumor targeting of anticancer drugs, improve absorption, transport, and in vivo stability, while increasing their effectiveness while reducing systemic adverse effects. Usually these goals are achieved by physically or chemically conjugating the drug to the carrier. [0003] T...

Claims

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Application Information

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IPC IPC(8): C08B37/16A61K47/69A61K47/54A61P35/00
CPCC08B37/0012
Inventor 丁毅力李紫元王丙云
Owner FOSHAN UNIVERSITY
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