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Quercetin derivatives and their preparation methods and applications

A derivative, quercetin technology, applied in the field of compound preparation and application, can solve problems such as unseen systematic research, achieve obvious pathological hyperplasia, pathological hyperplasia inhibition, and excellent inhibition of NRK-49F proliferation activity

Active Publication Date: 2017-12-19
南京盈博医药生物技术创新研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Quercetin directly participates in the reaction to obtain mixed products with multiple substitutions coexisting, so the selective protection of quercetin is an important step in the structural modification of quercetin, but there is no systematic study

Method used

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  • Quercetin derivatives and their preparation methods and applications
  • Quercetin derivatives and their preparation methods and applications
  • Quercetin derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 5

[0023] The synthesis of embodiment 1 five substituted quercetins and four substituted quercetins

[0024] Compound 2a: Dissolve quercetin 1 (500mg, 1.65mmol) in 15mL DMF, add acetic anhydride (1.25mL, 13.24mmol), triethylamine (2.76mL, 20mmol), stir the reaction system at room temperature for 3h, and detect the raw materials by TLC The reaction disappeared completely. The reaction solution was poured into ice water, a white solid was precipitated, the suspension was filtered to obtain a crude product, and the crude product was recrystallized with methanol to obtain a white compound 2a with a yield of 83%. Product characterization: 1 HNMR (300MHz, CDCl 3 ) δppm7.75–7.66 (m, 2H), 7.39–7.31 (m, 2H), 6.88 (d, J=1.9Hz, 1H), 2.43 (s, 3H), 2.34 (s, 6H), 2.34 (s , 6H). MS-ESI (m / z): [M+H] + : 513.10.

[0025] Compound 2b: Dissolve quercetin 1 (300mg, 1.00mmol) in 10mL DMF, add acetic anhydride (0.37mL, 4.00mmol), triethylamine (0.83mL, 6.00mmol), react the reaction system at roo...

Embodiment 2

[0031] The synthesis of embodiment 2 selective protection quercetin compounds

[0032] Compound 5: Quercetin 1 (302mg, 1.00mmol) was dissolved in 20mL of diphenyl ether, dichlorodiphenylmethane (300μL, 1.50mmol) was added, the reaction system was stirred at 175°C for 0.5h, and the raw materials basically disappeared as detected by TLC . After the reaction solution was cooled to room temperature, 50 mL of petroleum ether was added and a dark red solid was precipitated. The crude product was obtained by filtration. The crude product was subjected to column chromatography (PE:EtOAc=4:1) to obtain compound 5 with a yield of 86%. Product characterization: 1 HNMR (300MHz, DMSO-d 6 ) δppm 12.38 (s, 1H), 10.84 (s, 1H), 9.66 (s, 1H), 7.86–7.77 (m, 2H), 7.61–7.50 (m, 4H), 7.49–7.39 (m, 6H) , 7.20 (d, J=8.3Hz, 1H), 6.47 (d, J=2.0Hz, 1H), 6.19 (d, J=2.0Hz, 1H).

[0033] Compound 6: Compound 5 (932 mg, 2.00 mmol) was dissolved in 30 mL of acetone, and K 2 CO 3 (1.38g, 10.00mmol), BnB...

Embodiment 3

[0039] Synthesis of compound in the derivatization reaction of embodiment 3 intermediate 5

[0040] Compound 12a: Compound 5 (600 mg, 1.29 mmol) was dissolved in 20 mL of acetone, and K 2 CO 3 (1.4g, 10mmol), Me 2 SO 4 (0.61mL, 6.44mmol), the reaction system was stirred and reacted at 60°C for 3h, and TLC detected that the starting material disappeared completely. The reaction solution was filtered to remove inorganic salts, and the filtrate was spin-dried to obtain a crude product, which was subjected to column chromatography (PE:EtOAc=1:2) to obtain compound 12a with a yield of 75%. Product characterization: 1 HNMR (300MHz, CDCl 3 ) δppm7.72-7.66 (m, 2H), 7.64–7.56 (m, 4H), 7.44–7.36 (m, 6H), 6.99 (d, J=8.3Hz, 1H), 6.47 (d, J=2.2Hz , 1H), 6.33 (d, J=2.2Hz, 1H), 3.95 (s, 3H), 3.88 (s, 3H), 3.88 (s, 3H).

[0041] Compound 12b: Compound 5 (200 mg, 0.43 mmol) was dissolved in 15 mL of acetone, and K 2 CO 3 (326mg, 2.36mmol), diethyl sulfate (186μL, 2.14mmol), and the re...

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Abstract

The invention discloses a derivative of quercetin and its preparation method and application. In the preparation method, dichlorodiphenylmethane is used to protect the quercetin o-diphenol hydroxyl group, and combined with a benzyl protecting group to obtain selective protection. The quercetin derivatives are separately reacted with dimethyl sulfate, diethyl sulfate, allyl bromide, p-toluenesulfonyl chloride and acetic anhydride to generate corresponding quercetin derivatives. The prepared derivative compounds all showed better inhibitory activity of NRK-49F proliferation than quercetin. Among them, quercetin derivatives 20a‑1, 14a‑2 and 23d‑1, which were substituted by methyl group and p-toluenesulfonyl group, exhibited better inhibitory activity on NRK‑49F proliferation, and the inhibition rates reached 86.33%, 78.04%, 75.91%. It can be seen that the currently obtained quercetin-derived products have a significant inhibitory effect on the proliferation of renal fibroblast NRK-49F.

Description

technical field [0001] The invention relates to the technical field of compound preparation and application, in particular to a quercetin derivative and its preparation method and application. Background technique [0002] Quercetin is a polyphenolic hydroxyflavonol compound with the following chemical structure: [0003] [0004] Its characteristic structure is that besides the basic structure of chromone, it contains five phenolic hydroxyl groups. Quercetin has a wide range of pharmacological effects and biological activities, and has mild performance, low toxicity and side effects, and has very high medicinal value. Quercetin is a strong natural antioxidant, which can expand coronary blood vessels, lower blood pressure, protect myocardial ischemia, and resist platelet aggregation. It is also an active compound for anticancer, antibacterial, antiallergic, antiviral, and analgesic. Nevertheless, quercetin's relatively weak pharmacological activity and low bioavailabili...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04C07D311/30A61K31/36A61K31/352A61P1/16A61P13/12A61P11/00
CPCY02P20/55
Inventor 李建新
Owner 南京盈博医药生物技术创新研究院有限公司
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