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Chlorogenic acid analogue as well as preparation method and application thereof

A technology of analogs and chlorogenic acid, which is applied in the field of chlorogenic acid analogs and its preparation, can solve problems such as easy hydrolysis and instability of chlorogenic acid, achieve strong antioxidant activity, and have a simple preparation method, which is conducive to popularization and use Effect

Active Publication Date: 2022-07-22
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention intends to provide a chlorogenic acid analog and its preparation method and application to solve the problem of chlorogenic acid instability and easy hydrolysis

Method used

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  • Chlorogenic acid analogue as well as preparation method and application thereof
  • Chlorogenic acid analogue as well as preparation method and application thereof
  • Chlorogenic acid analogue as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] The present embodiment provides a chlorogenic acid analog, which is the following compound:

[0072]

[0073] The synthetic route of compound 8 is as follows:

[0074]

[0075] The preparation method of compound 8 includes:

[0076] a) Synthesis of compound 2:

[0077]

[0078] DMAP (0.338 g, 2.77 mmol) was weighed and dissolved in acetic anhydride (26 mL, 277 mmol), so that DMAP and acetic anhydride were fully reacted; then, compound 1 (quinic acid, 5 g, 27.7 mmol) was added, and the reaction system was added DIPEA (48 mL, 277 mmol). TCL monitoring: (DCM:methanol=10:1); After the reaction is over, NaHCO 3 The pH of the aqueous solution was adjusted to alkaline, and EA was used to extract impurities (discarded); 2mol / L HCl was adjusted to pH=2, EA was extracted, and anhydrous Na 2 SO 4 After drying, suction filtration, and spin drying, compound 2 was obtained with a yield of 100%, which was directly used in the next reaction without purification.

[0079] b...

Embodiment 2

[0099] This embodiment provides another chlorogenic acid analog, and the chlorogenic acid analog is the following compound:

[0100]

[0101] The synthetic route of compound 9 is as follows:

[0102]

[0103] Steps a) to e) in the preparation method of compound 9 are the same as steps a) to e) in the preparation method of compound 8, and the only difference is:

[0104] Step f) in the preparation method of compound 9 is as follows:

[0105] f) Synthesis of compound 9:

[0106]

[0107] Compound 7 (2.4 g, 3.5 mmol) was weighed and dissolved in 10 mL of methanol; triethylamine (10 mL, 2 mmol) was weighed and added to the reaction solution. TLC monitoring (DCM:MeOH=10:1), after the completion of the reaction, the crude product of compound 9 was obtained by removing the organic solvent. The crude product was purified by column chromatography (DCM:MeOH=40:1) to obtain pure compound 9 with a yield of 78%.

[0108] Hydrogen NMR spectrum of compound 9: 1 H NMR (400MHz, c...

Embodiment 3

[0110] This embodiment provides another chlorogenic acid analog, and the chlorogenic acid analog is the following compound:

[0111]

[0112] The synthetic route of compound 10 is as follows:

[0113]

[0114] Steps a) to f) in the preparation method of compound 10 are the same as steps a) to f) in the preparation method of compound 9, and the only difference is:

[0115] The preparation method of compound 10 also includes step g) as follows:

[0116] g) Synthesis of compound 10:

[0117]

[0118] Compound 9 (100 mg, 0.165 mmol) was weighed and dissolved in 10 mL of DMF; potassium carbonate (91.2 mg, 0.66 mmol) was weighed and added to the reaction solution, followed by methyl iodide (234 mg, 1.65 mmol), and the reaction was stirred at 80°C. TLC monitoring (DCM:MeOH=30:1), after the completion of the reaction, the reaction solution was diluted with water, extracted with EA 3 times, washed with saturated brine twice, the organic phases were combined and dried over an...

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Abstract

The invention belongs to the technical field of synthesis of chlorogenic acid analogues, and particularly relates to a chlorogenic acid analogue and a preparation method and application thereof.The chlorogenic acid analogue has high antioxidant activity and can be applied to preparation of antioxidant pharmaceutical preparations, and in the preparation method of the chlorogenic acid analogue, the antioxidant activity of the chlorogenic acid analogue is greatly improved. Two pharmacophores of caffeic acid and quinic acid are connected through a six-membered ring for the first time, and the chlorogenic acid analogue contains stable amido bonds, so that the defect that chlorogenic acid is easy to hydrolyze and loses activity is effectively overcome. In addition, the preparation method of the chlorogenic acid analogue is simple and is beneficial to popularization and application.

Description

technical field [0001] The invention belongs to the technical field of chlorogenic acid analog synthesis, in particular to a chlorogenic acid analog and a preparation method and application thereof. Background technique [0002] Chlorogenic acid (CGA) is a plant secondary metabolite and belongs to polyphenolic compounds. Studies have shown that CGA has various biological activities, such as antioxidant, anti-diabetic, anti-obesity, anti-inflammatory, anti-hypertensive, antibacterial, antiviral, antitumor, neuroprotective, etc. [0003] Studies have found that the antioxidant properties of CGA are related to the five active hydroxyl groups in the structure, which are beneficial to scavenge excess hydroxyl radicals and superoxide anions in the body, thereby exerting a strong antioxidant effect. However, due to the presence of chemically unstable ester bonds in the CGA molecule, only a small amount of chlorogenic acid is completely absorbed after oral administration. Therefor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58A61K31/4468A61P39/06
CPCC07D211/58A61P39/06C07B2200/07Y02P20/55
Inventor 黄强朱蕾王书奇罗会川
Owner ZUNYI MEDICAL UNIVERSITY
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