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A class of phenylboronic acid organogel compounds

An organic gel and compound technology, applied in the field of chemistry, can solve the problems of increased insulin blood sugar concentration, long response time of glucose molecule stimulation, and inability to synchronize

Inactive Publication Date: 2015-12-02
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the high molecular weight of the polymer gel material, the response time to the stimulation of glucose molecules is relatively long, resulting in the out-of-synchronization between the release of insulin and the increase in blood sugar concentration, which directly affects the therapeutic effect.
Therefore, the glucose-sensitive and fast-response insulin controlled-release carrier material that can realize the synchronous controlled release of insulin with the increase of blood glucose concentration has not been well developed.

Method used

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  • A class of phenylboronic acid organogel compounds
  • A class of phenylboronic acid organogel compounds
  • A class of phenylboronic acid organogel compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] (1) Add 3-aminophenylboronic acid (1.37g, 10mmol), neopentyl glycol (1.25g, 12mmol) and 30mL chloroform into a 100mL round bottom flask, and stir for 3h at room temperature. The reaction solution was washed twice with 200 mL of water, the organic phase was separated, dried with anhydrous sodium sulfate and filtered, and the filtrate was rotary evaporated to remove the solvent to obtain compound (3) 3-aminophenylboronic acid neopentyl glycol ester (C 11 h 16 BNO 2 , R=CH 3 ), the yield was 96%.

[0046] Make a few more pots according to the above method for subsequent reactions.

[0047] (2) Add 30mL of methanol to a 100mL round bottom flask, cool to 0°C, add 4mL of thionyl chloride, transfer to room temperature and stir for 30min, add phenylalanine (3.96g, 24mmol), and reflux at 70°C for 6h , after distilling off the solvent, compound (4), phenylalanine methyl ester hydrochloride (C 10 h 14 ClNO 2 ), the yield was 95%.

[0048] Make a few more pots according to ...

Embodiment 2

[0058] (1) Add 3-aminophenylboronic acid (1.37g, 10mmol), neopentyl glycol (1.56g, 15mmol) and 40mL chloroform into a 100mL round bottom flask, and stir at room temperature for 6h. The reaction solution was washed twice with 200 mL of water, the organic phase was separated, dried with anhydrous sodium sulfate and filtered, and the filtrate was rotary evaporated to remove the solvent to obtain compound (3) 3-aminophenylboronic acid neopentyl glycol ester (C 11 h 16 BNO 2 , R=CH 3 ), the yield is 95%.

[0059] Make a few more pots according to the above method for subsequent reactions.

[0060] (2) Add 39mL of methanol to a 100mL round bottom flask, cool to 0°C, add 5.2mL of thionyl chloride, transfer to room temperature and stir for 30min, add phenylalanine (3.96g, 24mmol), and reflux at 70°C for 12h Finally, after distilling off the solvent, compound (4), phenylalanine methyl ester hydrochloride (C 10 h 14 ClNO 2 ), the yield was 97%.

[0061] Make a few more pots acco...

Embodiment 3

[0070] (1) Add 3-aminophenylboronic acid (1.37g, 10mmol), neopentyl glycol (1.06g, 10mmol) and 12mL chloroform into a 100mL round bottom flask, and stir at room temperature for 1h. The reaction solution was washed twice with 70 mL of water, the organic phase was separated, dried with anhydrous sodium sulfate and filtered, and the filtrate was rotary evaporated to remove the solvent to obtain compound (3) 3-aminophenylboronic acid neopentyl glycol ester (C 11 h 16 BNO 2 , R=CH 3 ), the yield is 95%.

[0071] Make a few more pots according to the above method for subsequent reactions.

[0072] (2) Add 15mL of methanol to a 100ml round bottom flask, cool to 0°C, add 2.1mL of thionyl chloride, transfer to room temperature and stir for 30min, then add phenylalanine (3.96g, 24mmol), and reflux at 70°C for 5h Finally, after distilling off the solvent, compound (4), phenylalanine methyl ester hydrochloride (C 10 h 14 ClNO 2 ), the yield was 92%.

[0073] Make a few more pots a...

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Abstract

The invention discloses a phenylboronic acid organogel compound with a formula (I) as shown in the specification, a preparation method of the compound, and an application of the compound as a gelata to preparation of glucose sensitive organogels, and n in the formula (I) is the integer selected from 1-16.

Description

(1) Technical field [0001] The invention relates to the synthesis of a class of phenylboronic acid organic gel compounds and the preparation of the gel, which belongs to the technical field of chemistry. (2) Background technology [0002] Insulin self-regulated controlled release system is of great significance to the treatment of insulin-dependent diabetes (ZhaoY.N., TrewynB.G., SlowingI.I., LinV.S.Y.J.Am.Chem.Soc., 2009, 131, 8398-8400. ), by feeding back the glucose concentration signal in the body and automatically and continuously controlling the release of insulin, so that diabetic patients can get rid of the pain caused by long-term insulin injection (SiegelR.A., GuY.D., LeiM., BaldiA., NuxollE.E. , Ziaie B. J. Control. Release, 2010, 141, 303-313; Ravaine V., Ancla C., Catargi B. J. Control. Release, 2008, 132, 2-11.). At present, research on glucose-sensitive gels is mainly focused on polymer gel materials containing phenylboronic acid groups, such as phenylboronic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/04A61K47/24A61K9/06A61K38/28A61P3/10
Inventor 高文霞徐龙吴华悦陈久喜刘妙昌黄小波蒋俊
Owner WENZHOU UNIV