Glucoside containing azobenzene group, and preparation method and application thereof

A technology of azophenyl and nitrogen phenyl, which is applied in the field of catalytic reaction engineering and can solve problems such as difficult to meet

Active Publication Date: 2014-09-24
完美(广东)日用品有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, in the azobenzene photosensitive liposomes that have been developed and applied, although their photoresponsiveness is satisfied, the stability of the liposome structure, especially the biological targeting and biocompatibility in vivo And in vivo degradability, there are still big deficiencies, it is difficult to meet the growing demand

Method used

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  • Glucoside containing azobenzene group, and preparation method and application thereof
  • Glucoside containing azobenzene group, and preparation method and application thereof
  • Glucoside containing azobenzene group, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Example 1 Synthesis of intermediate 4'-n-butyl-1-azobenzene-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

[0100] Specifically include the following steps:

[0101] (1) Coupling reaction of aromatic diazonium salt: Synthesis of compound 4-n-butyl-4'-hydroxyazobenzene (1)

[0102]

[0103] Mix 4-n-butylaniline (0.27mL) with water and concentrated hydrochloric acid and stir evenly for 1h, cool to 0-5°C, add NaNO 2 (116mg) aqueous solution stirring reaction 30min, keep temperature constant, add phenol (158mg) and Na 2 CO 3 (530mg) in aqueous solution, stirring the reaction until the reaction is complete. After the reaction, the pH of the reaction solution was adjusted to ≈3 with concentrated hydrochloric acid. Add 20ml of dichloromethane (CH 2 Cl2 ). use CH 2 Cl 2 Extraction (4×15 mL), combined organic layers, washed with water, washed with saturated NaCl, dried over anhydrous magnesium sulfate. After being dried well, it was filtered, and the filtrate was dist...

Embodiment 2

[0112] Example 2 Synthesis of 4'-n-butyl-1-azobenzene-α-D-galactopyranoside (4)

[0113]

[0114] The orange crystalline product (3) (120mg) obtained in Example 1 was dissolved in anhydrous methanol (2.4mL), triethylamine (0.3mL) and water (0.3mL) were added, and the volume of triethylamine, water and methanol was The ratio was 1:1:8, and the reaction was stirred at room temperature for 24h. After the completion of the reaction as detected by TLC, the solvent was evaporated from the reaction solution under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane / methanol) to obtain compound (4) as a pale yellow solid. The yield of compound (4) prepared from compound (2) was 85.8%, and the total yield of compound (4) prepared by the four-step reaction was 58.7%.

[0115] The compound obtained above is characterized by chemical structure, and its data are as follows:

[0116] 1 HNMR (400MHz, DMSO-d 6 )δ7.86(d, J=8.9Hz, 2H), 7.77(...

Embodiment 3

[0119] Example 3 Synthesis of intermediate 4'-n-heptyl-1-azobenzene-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

[0120] Specifically include the following steps:

[0121] (1) Coupling reaction of aromatic diazonium salt: Synthesis of compound 4-n-heptyl-4'-hydroxyazobenzene (5)

[0122]

[0123] Concentrated hydrochloric acid (0.9 mL, 10.8 mmol, 5.4 eq) was added to a mixture of 4-n-heptylaniline (2 mmol, 1 eq) and water (3 mL), and stirred at room temperature for 1 h. The reaction solution was cooled to 0-5°C in an ice-water bath, and the NaNO 2 A solution of (137.99mg, 2mmol, 1eq) in water (2mL) was slowly added dropwise (about 20s / drop) into the reaction flask, and stirred for 30min. Keep 0~5℃, add phenol (188.22mg, 2mmol, 1eq) to the reaction solution, slowly add Na 2 CO 3 (635.94mg, 6mmol, 3eq) in water (7mL) solution, the pH of the reaction solution was measured by pH test paper = 8-10, and the reaction solution was stirred at 0-5°C for 3h. TLC was used to chec...

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Abstract

The invention belongs to the field of catalytic reaction engineering, and particularly relates to synthetic glucoside containing an azobenzene group, and application of the glucoside serving as an ultraviolet controlled-release material. The glucoside containing an azobenzene group has a structure as shown in Formula (I). The glucoside containing an azobenzene group can be used for preparation of ultraviolet sensitive liposome, and has favorable structural stability, biological targeting property, biocompatibility and in-vivo degradability.

Description

technical field [0001] The invention belongs to the field of catalytic reaction engineering, and in particular relates to a synthesized azophenyl-containing glycoside and its use as an ultraviolet light-controlled release material. Background technique [0002] Liposome, also known as liposome, is a new type of pharmaceutical preparation with targeted drug delivery function. Liposome is a preparation formed by encapsulating drug molecules in vesicles formed by phospholipid bimolecular membranes. Since the basic structure of the biological plasma membrane is also a phospholipid bimolecular membrane, liposomes have a structure similar to that of biological cells, so they have good biocompatibility. Liposomes have certain targeting, lymphatic orientation and good sustained-release effect, and are often used as drug carriers. [0003] At present, people have been working on how to improve the structural stability of their vesicles in the research on the application of liposome...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00A61K9/127A61K47/26
Inventor 胡瑞连李子安段朝辉徐首红陈汝婷刘洪来
Owner 完美(广东)日用品有限公司
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