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A kind of salidroside-biotin small molecule probe and its preparation method and application

A small-molecule probe, salidroside technology, applied in the field of salidroside-biotin small-molecule probe and its preparation, achieves the effects of mild reaction conditions, short route, good water solubility and

Active Publication Date: 2022-02-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the above-mentioned prior art, the present invention provides a salidroside-biotin small molecule probe and its preparation method and application, so as to overcome the deficiencies in the existing research on the target of salidroside and the mechanism of cardiomyocyte damage protection

Method used

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  • A kind of salidroside-biotin small molecule probe and its preparation method and application
  • A kind of salidroside-biotin small molecule probe and its preparation method and application
  • A kind of salidroside-biotin small molecule probe and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of salidroside nitrate (VII)

[0040]

[0041] In a 25 mL round bottom flask, 97 mg of iodobenzene diacetoxyacetate, 142 mg of ferric nitrate nonahydrate and acetonitrile (8 mL) were added, and 300 mg of salidroside (VI) was added. The reaction solution was stirred and reacted at 65°C for 6 hours. The reaction solution was filtered with suction to remove insoluble matter, and then concentrated. The concentrate was subjected to silica gel column chromatography. The eluent used in the chromatography was a mixture of dichloromethane and methanol at a volume ratio of 10:1. The eluate was evaporated to remove the solvent to obtain 245 mg of yellow solid with a yield of 71%.

[0042] The spectral data analysis of compound VII is as follows:

[0043] 1 H NMR (CD 3 OD,500MHz)δ2.83(t,J=6.75Hz,2H),3.06-3.09(m,1H),3.10-3.11(m,2H),3.20-3.21(m,1H),3.22-3.27(m ,1H),3.54-3.55(m,1H),3.65-3.69(m,1H),3.75-3.78(m,1H),3.91-4.03(m,1H),4.19(d,J=7.8Hz,1H ...

Embodiment 2

[0046] Embodiment 2: the preparation of salidroside nitrate (VII)

[0047]In a 25 mL round bottom flask, 118 mg of bis(tert-butylcarbonyloxy)iodobenzene, 131 mg of ferric nitrate nonahydrate and acetonitrile (8 mL) were added, and 290 mg of salidroside were added. The reaction solution was stirred and reacted at 55°C for 10 h, the reaction solution was filtered with suction to remove insoluble matter, and then concentrated, and the concentrate was subjected to silica gel column chromatography. The eluent used in the chromatography was a mixture of dichloromethane and methanol at a volume ratio of 10:1. The eluate was evaporated to remove the solvent to obtain 219 mg of a yellow solid with a yield of 66%.

Embodiment 3

[0048] Embodiment 3: the preparation of salidroside nitrate (VII)

[0049] In a 25 mL round bottom flask, 134 mg of [bis(trifluoroacetoxy)iodo]benzene, 148 mg of ferric nitrate nonahydrate and acetonitrile (8 mL) were added, and 310 mg of salidroside were added. The reaction solution was stirred and reacted at 50°C for 6 hours. The reaction solution was filtered to remove insoluble matter, and then concentrated. The concentrate was subjected to silica gel column chromatography. The eluent used in the chromatography was a mixture of dichloromethane and methanol at a volume ratio of 10:1. The eluate was evaporated to remove the solvent to obtain 306 mg of a yellow solid with a yield of 86%.

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Abstract

The invention discloses a salidroside-biotin small molecule probe, a preparation method and application thereof, and belongs to the field of medicinal chemistry. The structural formula of the small molecule probe in the present invention includes three parts: salidroside, biotin and connecting chain. The salidroside small-molecule probe designed by the present invention has been tested for in vitro activity, and the results show that it has good activity in protecting the primary cardiomyocyte injury induced by hypoxia-reoxygenation, and can be used as a small-molecule probe for rhodoside The research on the mechanism of action of Tianglycoside has a good application prospect in the medical field.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a salidroside-biotin small molecule probe and a preparation method and application thereof. Background technique [0002] Rhodiola L. is a perennial herb or subshrub of Crassulaceae. It is a traditional Chinese medicine in my country. There are records. Rhodiola plants have the effects of benefiting the lungs and spleen, promoting blood circulation and removing blood stasis. Modern research has found that Rhodiola plants have various pharmacological effects such as anti-hypoxia, fatigue, tumors, radiation, and aging. Salidroside is one of the main active compounds of Rhodiola, and its aglycone is p-hydroxyphenylethyl alcohol, namely tyrosol. Pharmacological studies have shown that salidroside can protect cardiomyocytes, improve vascular function, resist atherosclerosis, protect nerve cells, etc., and can be used to prevent and treat cardiovascular and cer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18C07H1/00A61K31/7056A61P9/00
CPCC07H15/18C07H1/00A61P9/00
Inventor 王书芳王毅张兴贤
Owner ZHEJIANG UNIV
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