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Quercetin derivative and preparation method and application thereof

A derivative, quercetin technology, applied in the field of medicine, can solve problems such as poor fat solubility, low drug efficacy, and limited application

Active Publication Date: 2017-05-17
西安天一生物技术股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Quercetin has multiple biological activities such as dilating coronary vessels, lowering blood lipids, anti-platelet aggregation, anti-inflammation, anti-allergic, anti-diabetic complications, etc., but its poor fat solubility, short half-life and low efficacy limit its application

Method used

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  • Quercetin derivative and preparation method and application thereof
  • Quercetin derivative and preparation method and application thereof
  • Quercetin derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of Quercetin Derivatives (1) and (5)

[0021] Add 122 mg (1.5 mmol) of formaldehyde solution, 175 mg (1.5 mmol) of concentrated ammonia water, 302 mg (1 mmol) of quercetin and 5 mL of ethanol into a closed pressure-resistant reactor, add 3 drops of hydrochloric acid, and heat to 75- React at 80°C for 3 hours, cool naturally, precipitate a solid, filter with suction, and separate the crude product by chromatography (V (n-butanol): V (water): V (HOAc) = 4:1:1, eluted with methanol to obtain intermediate Body (a) 105 mg light yellow solid, yield 31.7%. m.p.>300℃; 1 H NMR (400 MHz, DMSO-d 6 )δ: 7.74 (d,1H), 7.60 (d, 1H), 6.92 (d, 1H), 6.19 (s, 1H), 3.86 (s, 2H).

[0022] N 2 Under protection, 331 mg (1.0 mmol) of intermediate (a) and 130.5 mg (1.5 mmol) of 2-oxazolidinone were mixed, heated to 120°C for 2 hours, cooled to 0°C, and 141.6 mg (1.2 mmol) of SOCl was added 2 , heated to 100°C for 2 hours, cooled, added 15 mL of water, precipitated solid, filtered...

Embodiment 2

[0027] Preparation of Quercetin Derivatives (2) and (6)

[0028] 154.5 mg (1.5 mmol) 2-oxazolethione was used to replace 130.5 mg (1.5 mmol) 2-oxazolidinone in Example 1, and other operations were the same as in Example 1 to obtain 190.7 mg of compound (2) yellow solid, Compound (6) was obtained as a yellow solid 197.9 mg, m.p. were >300°C; compound (2) 1 H NMR (400 MHz, DMSO-d 6 )δ: 7.73 (d, 1H), 7.59 (d,1H), 6.89 (d, 1H), 6.79 (s, 1H), 6.18 (s, 1H), 4.24-4.10 (t, 2H), 3.88 (s ,2H), 3.87-3.80 (m, 1H). EIS [M-Na] + = 458.0. Compound (6) 1 H NMR (400 MHz, DMSO-d 6 )δ: 7.72 (d, 1H), 7.59 (d, 1H), 6.88 (d, 1H), 6.79 (s, 1H), 6.17 (s, 1H),4.24-4.10 (t, 2H), 3.87 (s , 2H), 3.87-3.80 (m, 1H), 3.71 (s, 15H). EIS [M+Na] + = 574.0.

Embodiment 3

[0030] Preparation of Quercetin Derivatives (3)

[0031] Replace 759 mg (5.5 mmol) of K in Example 1 with 300 mg (8.1 mmol) of anhydrous NaOAc and 7 mL of acetic anhydride 2 CO 3 and 781 mg (5.5 mmol) CH 3 I, reflux reaction for 2 hours, after the reaction was completed, poured into 100 mL of ice water, filtered, washed with water until neutral, dried, recrystallized from 95% ethanol, other operations were the same as in Example 1, and 230.9 mg of compound (3) was obtained as a yellow solid, m.p.> 300°C;1 H NMR (400 MHz, DMSO-d 6 )δ: 7.73 (d, 1H), 7.59 (d, 1H), 6.89 (d, 1H), 6.79 (s, 1H), 6.18 (s, 1H), 4.24-4.10 (t, 2H), 3.88 (s , 2H), 3.87-3.80 (m,1H), 2.04 (s, 15H). EIS [M+Na] + = 698.1.

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Abstract

The invention discloses a quercetin derivative and a preparation method and application thereof. The preparation method comprises the following steps of firstly, mixing quercetin, formaldehyde and ammonia to prepare Mannich alkaline of the quercein; reacting with 2-oxazolidine (thio)one and SOCl2; protecting phenolic hydroxyl of the quercetin, oxidizing by NaNO2, and removing protecting groups, so as to obtain the quercetin derivative. The prepared quercetin derivative can be used for inhibiting brain tumors and central nervous system tumors via blood brain barrier.

Description

technical field [0001] The invention relates to derivatives of quercetin and their application in pharmacy, which belong to the technical field of medicine. Background technique [0002] Utilizing the rich resources of Chinese herbal medicines in my country, separating and extracting the active ingredients and using them as precursors to modify their structures to improve their drug delivery routes, enhance their pharmacological activity, and reduce toxic and side effects are important for realizing the modernization of Chinese medicine and innovating new drugs. way. [0003] Quercetin has multiple biological activities such as dilating coronary blood vessels, lowering blood lipids, anti-platelet aggregation, anti-inflammation, anti-allergic, anti-diabetic complications, etc., but its poor fat solubility, short half-life and low efficacy limit its application. In recent years, the effect of quercetin on tumor chemoprevention and treatment has attracted more and more attentio...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61P35/00
CPCC07D311/30Y02P20/55
Inventor 张宝华张冀男史兰香刘斯婕郭瑞霞
Owner 西安天一生物技术股份有限公司
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