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Tyrosol-biotin small molecular probe as well as preparation method and application thereof

A technology of small molecule probes and biotin, which is applied in the direction of drug combination, antidote, cardiovascular system diseases, etc., to achieve the effect of simple operation, mild reaction conditions and high selectivity

Active Publication Date: 2021-04-13
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a common labeling group, biotin has not been reported so far as the "biotin-tyrosol" small molecule probe formed by the connection of biotin-tyrosol to catch its target.

Method used

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  • Tyrosol-biotin small molecular probe as well as preparation method and application thereof
  • Tyrosol-biotin small molecular probe as well as preparation method and application thereof
  • Tyrosol-biotin small molecular probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of 2-nitrotyrosol (VII)

[0042]

[0043] In a 50 mL round bottom flask, add 934 mg of iodobenzene diacetoxy acetate, 1.3 g of zinc nitrate hexahydrate and 25 mL of acetonitrile, and add 2.0 g of 2-aminotyrosol (VI). The reaction solution was reacted at room temperature overnight, TLC detected that the raw materials were basically reacted completely, water was added, extracted with ethyl acetate, and the organic phase was concentrated to obtain 1.67 g of a tan solid with a yield of 63%.

Embodiment 2

[0044] Embodiment 2: the preparation of 2-nitrotyrosol (VII)

[0045] In a 50 mL round bottom flask, add 1.47 g of bis(tert-butylcarbonyloxy)iodobenzene, 1.3 g of zinc nitrate hexahydrate and 25 mL of acetonitrile, and add 2.0 g of tyrosol. The reaction solution was reacted at room temperature overnight, TLC detected that the raw materials were basically reacted completely, water was added, extracted with ethyl acetate, and the organic phase was concentrated to obtain 1.59 g of a brownish yellow solid with a yield of 60%.

Embodiment 3

[0046] Embodiment 3: the preparation of 2-nitrotyrosol (VII)

[0047] In a 50 mL round bottom flask, 1.25 g of [bis(trifluoroacetoxy)iodo]benzene, 1.3 g of zinc nitrate hexahydrate and 25 mL of acetonitrile were added, and 2.0 g of tyrosol was added. The reaction solution was reacted overnight at room temperature. TLC detected that the raw materials were basically reacted completely. Water was added, extracted with ethyl acetate, and the organic phase was concentrated to obtain 2.12 g of a brownish-yellow solid with a yield of 80%.

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Abstract

The invention discloses a tyrosol-biotin small molecular probe as well as a preparation method and application thereof. The structural formula of the tyrosol small molecular probe comprises tyrosol, biotin and a connecting chain. In-vitro activity tests show that the tyrosol small molecular probe designed by the invention has good activity in protection of hypoxia-reoxygenation induced primary myocardial cell damage, can be used as a small molecular probe for tyrosol action mechanism research, and 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 tyrosol-biotin small molecule probe and its preparation method and application. Background technique [0002] Tyrosol is the aglycone of salidroside, one of the main active ingredients in Rhodiola plants, and one of the main phenolic compounds in olive oil, which has strong antioxidant activity. Tyrosol has shown good pharmacological activities in the prevention and treatment of nervous system diseases, protection of the heart, liver and kidneys, inhibition of inflammation, inhibition of oxidative stress, antithrombotic, anti-atherogenic, anti-pathogenic microorganisms, anti-tumor, etc. . Oxidative stress is one of the important mechanisms of ischemia-reperfusion-induced myocardial injury. Ischemia-reperfusion injury leads to excessive accumulation of ROS and can trigger myocardial cell death, leading to heart failure. Studies have shown that tyrosol c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61P9/00A61P9/10A61P39/06
CPCA61P9/00A61P9/10A61P39/06C07D495/04
Inventor 王书芳王毅张兴贤
Owner ZHEJIANG UNIV
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