Optical pure 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol and applications thereof

A kind of technology of oxazepine and tetrahydrobenzene, applied in the application field of phospholipase C

Active Publication Date: 2016-02-03
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some studies have reported compounds containing benzo[b][1,4]oxazepine structural units, there are few reports about optically pure (R-type and S-type) 7-amino-2,3,4,5-tetrahydro Benzo[b][1,4]oxazepine-3-ol and its application in inhibiting the activity of bacterial PC-PLC have not been reported at home and abroad at present

Method used

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  • Optical pure 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol and applications thereof
  • Optical pure 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol and applications thereof
  • Optical pure 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Preparation of (R)-7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol

[0040] At reflux temperature, the EtOH / H 2 Iron powder (1.008 g, 18 mmol) was added to O (ethanol / water) (v / v=1:1, 300 mL) solution. The reaction mixture was continued to reflux for 1 hour. Cool to room temperature to saturate Na 2 CO 3 The solution was adjusted to pH=8, filtered with celite, concentrated to remove ethanol in the filtrate, and extracted with ethyl acetate (15 mL×3). Wash the organic phase with water, anhydrous MgSO 4 Dry, conventionally filter and concentrate to obtain crude product of (R)-7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol.

[0041] The above crude product was separated by silica gel column chromatography (petroleum ether / ethyl acetate=1:3) to obtain pure (R)-7-amino-2,3,4,5-tetrahydrobenzo[b][1, 4] Oxazepine-3-ol (60% yield).

[0042] The structural formula of (R)-7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-3-alcohol is as follows:

[00...

Embodiment 2

[0056] Example 2: Preparation of (S)-7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol

[0057] Replace (R)-2,4-dinitrophenoxymethyl oxirane with (S)-2,4-dinitrophenoxymethyl oxirane, through similar to that described in Example 1 During the preparation process, (S)-7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol was obtained (55% yield).

[0058] The structural formula of (S)-7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-3-alcohol is as follows:

[0059]

[0060] Molecular formula: C 9 h 12 N 2 o 2

[0061] Molecular weight: 180.2

[0062] Appearance: white solid

[0063] Melting point: 187-189°C

[0064] Specific rotation

[0065] The infrared spectrum data are as follows:

[0066] IR(ν max cm -1 ):3397,2920,1612,1515,1217,1106;

[0067] The NMR data are as follows:

[0068] 1 HNMR(d 6 -DMSO,400MHz):δ(ppm)2.89(dd,1H,J 1 =11.2,J 2 =7.9,CH),3.20(dd,1H,J 1 =11.2,J 2 =4.5,CH),3.59(dd,1H,J 1 =11.8,J 2 =5.6, CH), 3.78 (m, 1H, CH), 4.02 (dd, 1H...

Embodiment 3

[0071] The influence of embodiment 3R type and S type 7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol on the activity of bacterial PC-PLC

[0072] Experimental group: The concentration of PC-PLC purified from Bacillus cereus was 0.15 U / mL, and D609, R type and S type 7-amino-2,3,4,5-tetrahydro Benzo[b][1,4]oxazepine-3-ol was mixed with 0.015U (0.15U / mL) Bacillus cereus PC-PLC and diluted to 100uL, and incubated at 37°C for 3h. Control group: 0.02% DMSO (v / v) was used instead of 0.015 U (0.15 U / mL) PC-PLC of Bacillus cereus, and then the PC-PLC activity was detected with AmplexRed PC-PLC-specific assay kit (Molecular Probes Inc., A12218).

[0073] The results showed that compared with the experimental group D609, 5μM R-type and S-type 7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-3- Alcohol treatment group just can obviously inhibit the activity of Bacillus cereus PC-PLC, and D609 has no effect under the same concentration (see attached figure 1 ), it can be seen that...

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Abstract

The invention discloses an optical pure 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol, wherein the structural formula of an R-type 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol compound is as shown in a formula (I), and the structural formula of an S-type 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol compound is as shown in a formula (II). The invention also discloses application of the compounds in inhibiting the activity of phosphatidylcholine-specific phospholipase C (PC-PLC). According to the optical pure 7-amino-2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine-3-ol provided by the invention, a situation that the R-type / S-type 7-amino-2,3,4,5- tetrahydrobenzo[b] [1,4]oxazepine-3-ol compound as an effective tool lays a foundation for the research on the activity inhibition of bacterial PC-PLC and the research, preparation and development of relevant human disease treatment drugs caused by PC-PLC is found.

Description

technical field [0001] The present invention relates to 7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-3-alcohol and its application, especially to optically pure (R-type and S- Type) 7-amino-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-3-ol and its activity in inhibiting bacterial phosphatidylcholine-specific phospholipase C ( PC-PLC) applications. Background technique [0002] PC-PLC, phosphatidylcholine-specific phospholipase C, is one of the important members of the phospholipase family, which can specifically hydrolyze the third phosphate bond of glycerophospholipid molecules to release phosphorylcholine and diacylglycerol. PC-PLC is an important enzyme ubiquitously present in various cells, and its basic biochemical characteristics, functions and subcellular distribution are cell-specific. It regulates the apoptosis of various cells, the proliferation, metastasis and differentiation of tumor cells by participating in cell signal transduction; in addition, PC-PLC is not...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D267/14A61P31/04
CPCC07D267/14
Inventor 苗俊英赵宝祥张尚立苏乐赵静路玮赵璇
Owner SHANDONG UNIV
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