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Quinic acid derivative and preparation method and application thereof

A technology of derivatives and quinic acid, applied in the preparation of sulfonamides, carboxylic acid amides, organic compounds, etc., can solve problems such as easy hydrolysis, short half-life, and unstable structure of dicaffeoyl compounds

Active Publication Date: 2019-09-10
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Studies have shown that these dicaffeoyl compounds are unstable in structure, easily hydrolyzed in blood, and have a short half-life, which directly affects the clinical application of these natural products

Method used

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  • Quinic acid derivative and preparation method and application thereof
  • Quinic acid derivative and preparation method and application thereof
  • Quinic acid derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Example 1 Preparation of N-methyl-N', N'-dicaffeoyl-3,4-diamino-1,5-dihydroxycyclohexane-1-carboxamide (CL-01~CL-04) and separation and purification

[0139] (1) Preparation of (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylic acid

[0140] (1a) Preparation of benzo[d][1,3]dioxolene (pipercycline)

[0141] Weigh catechol (110.1 mg, 1.0 mmol) into a 50 mL round bottom flask, add 15 mL of N,N-dimethylformamide, stir to dissolve the catechol, then add diiodomethane (321.4 mg, 1.2mmol) and sodium bicarbonate (210.0mg, 2.5mmol), heated at 80°C for 12h. After the reaction was completed, the product was slowly poured into ice water while stirring, extracted 3 times with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, ethyl acetate was removed by rotary evaporation under reduced pressure, and silica gel column chromatography (Beijing Shinwell Glass Instrument Co., Ltd. Co., Ltd.) separation and purification (petroleum ether: ethyl acetate = 10:1, V:V) to obta...

Embodiment 2

[0171]Example 2 Preparation of N-methyl-N', N'-dicaffeoyl-3,5-diamino-1,4-dihydroxycyclohexane-1-carboxamide (CL-05~CL-08) and separation and purification

[0172] (1) The preparation of (E)-3-(benzo[d][1,3]dioxopenten-5-yl)acrylic acid was carried out according to the step (1) in Example 1.

[0173] (2) Preparation of N-methyl-3,5-diamino-1,4-dibenzyloxycyclohexane-1-carboxamide

[0174] (2a) The preparation of methyl quinic acid was carried out according to (2a) in the step (2) of Example 1.

[0175] (2b) The preparation of N-methylquinic amide was carried out according to (2b) in step (2) of Example 1.

[0176] Preparation of (2c')N-methyl-3,5-bis(tert-butyldimethylsilyloxy)quininamide

[0177] Weigh the N-methylquinine amide (1.74g, 8.5mmol) that step (2b) obtains in the dry 100mL round-bottomed flask, dissolve with an appropriate amount of dry THF, then add imidazole (3.50mg, 51.0 mmol), and finally a solution of tert-butyldimethylsilyl chloride (TBSCl) (2.33 g, 20.5 ...

Embodiment 3

[0196] Example 3 N-methyl-N', N'-dicaffeyl-3,4-diamino-1,5-dihydroxycyclohexane-1-carboxamide (CL-09~CL-12) Preparation and separation and purification

[0197] (1a-b) The preparation of (E)-2-(benzo[d][1,3]dioxopenten-5-yl)ethylene-1-sulfonic acid according to the procedure in Example 1 step (1) (1a) and (1b) yield piperonal.

[0198] Preparation of (1c')(E)-2-(benzo[d][1,3]dioxol-5-yl)ethylene-1-sulfonic acid

[0199] In a 250 mL round bottom flask, piperonal (12 g, 79.9 mmol) and methanesulfonic anhydride (20.9 g, 120 mmol) obtained in step (1a-b) were dissolved in 150 mL of dry THF, and NaH (2.9 g, 120 mmol) was added in portions , and then the reaction solution was moved to an oil bath at 115° C. and heated to reflux for about 2 hours. The reaction process was monitored by TLC until the complete disappearance of piperonal, indicating that the reaction was complete. After the reaction solution was cooled to room temperature, the reaction solution was slowly poured into...

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Abstract

The invention discloses a quinic acid derivative and a preparation method and application thereof. The quinic acid derivative has a structure represented by a formula I, wherein R1, R2 and R3 are OH or AcNH; R1 = OH, R2 = R3 = AcNH, or R2 = OH, R1 = R3 = AcNH, or R3 = OH, R1 = R2 = AcNH; * represents an R configuration or an S configuration; and Ac represents caffeoyl CAc or a derivative caffesulfonyl SAc, and coffee(mono-methyl ester)phosphonyl PAc. The quinic acid derivative has the advantages of mild preparation conditions, simple and safe operation, high product purity and relatively hightotal yield, and the obtained quinic acid derivative can be used for preparing medicaments for treating viral infections, especially for preparing medicaments for treating influenza virus, parainfluenza virus and respiratory syncytial virus infections.

Description

technical field [0001] The invention belongs to the field of antiviral infection drugs, in particular to a quinic acid derivative and its preparation method and application. Background technique [0002] As we all know, respiratory virus infection is one of the infectious diseases that seriously endanger human health, among which influenza virus, parainfluenza virus and respiratory syncytial virus (RSV) are the main pathogens of respiratory virus infection. RSV is the second most common respiratory tract infection virus after influenza A virus. The susceptible population is mainly infants and young children, which can cause severe lower respiratory tract infections such as acute bronchitis, bronchitis, and pneumonia in infants and young children. According to statistics, about 95% of children were infected with RSV before the age of 2, and 100% of children were infected with RSV before adulthood (Piedimonte, G., et al. Pediatrics in Review 2014,35:519-530). Worldwide, RSV i...

Claims

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Application Information

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IPC IPC(8): C07C237/24C07C231/12C07C311/27C07C303/40C07F9/44A61P31/16A61P31/14A61K31/664A61K31/18A61K31/165
CPCC07C237/24C07C311/27C07F9/4473A61P31/16A61P31/14C07C2601/14
Inventor 陈河如李药兰李满妹吴东辉唐维饶舒文何业谱
Owner JINAN UNIVERSITY
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