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Flavonoid derivatives and preparation method thereof and application in preparation of immunoenhancer

A technology of immune enhancers and derivatives, which is applied in the fields of drug combination, organic chemistry, allergic diseases, etc., and can solve problems such as undiscovered immune enhancers

Active Publication Date: 2020-01-03
OCEAN UNIV OF CHINA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, no research patents or other literature reports have been found on flavonoid-based immunopotentiators for promoting T cell proliferation

Method used

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  • Flavonoid derivatives and preparation method thereof and application in preparation of immunoenhancer
  • Flavonoid derivatives and preparation method thereof and application in preparation of immunoenhancer
  • Flavonoid derivatives and preparation method thereof and application in preparation of immunoenhancer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: The synthetic route of flavonoid derivative YSW-01 is as follows:

[0034]

[0035] Add flavonoid derivative b (678mg, 1mmol), o-benzyloxybenzoic acid a (273.6mg, 1.2mmol), DMAP (183mg, 1.5mmol) into a 100ml one-port bottle, add 25ml of DMF, the system is in a suspended state, and finally add EDCI (287mg, 1.5mmol), after 1-2 hours, the system slowly dissolves, stir at room temperature overnight for 14h, TLC detects the reaction, after the basic reaction of the raw materials is complete, the system is poured into water, a yellow solid is precipitated, suction filtration, column chromatography For purification, petroleum ether was added, ultrasonication, beating at room temperature, and filtration to obtain 600 mg of a yellow solid with a yield of 67.5%.

[0036] 1 H NMR (500MHz, dmso-d 6 )δ12.11(s, 1H), 8.19(d, J=7.8Hz, 1H), 7.69(d, J=8.6Hz, 1H), 7.51(d, J=7.5Hz, 2H), 7.46-7.20( m, 26H), 7.16(t, J=7.6Hz, 1H), 6.98(s, 1H), 6.61(d, J=1.7Hz, 1H), 5.30(s,...

Embodiment 2

[0037] Example 2: The synthetic route of flavonoid derivative YSW-TM1 is as follows:

[0038]

[0039] The YSW-01 (600 mg, 0.675 mmol) prepared in Example 1 was dissolved in about 20 ml of MeOH, 100 mg of 10% Pd / C was added, and the double-layered hydrogen balloon was reacted overnight at room temperature, TLC (PE:EA=3: 1) The disappearance of raw materials was detected, and the main product was detected by LCMS. A small amount of diatomaceous earth was filtered to remove Pd-C to obtain a red solution, and the solvent was evaporated to dryness to obtain a yellow oil, which was purified by column chromatography to obtain 200 mg of a yellow solid with a yield of 67.8%. LCMS Detection ESI(-)[M-H]=437.

[0040] 1 H NMR (500MHz, dmso-d 6 )δ12.14(s, 1H), 11.03(s, 1H), 10.19(s, 1H), 9.37(s, 2H), 9.07(s, 1H), 8.03(dd, J=7.9, 1.4Hz, 1H ), 7.67-7.56(m, 1H), 7.09-7.00(m, 2H), 6.95(s, 2H), 6.49(d, J=1.9Hz, 1H), 6.27(d, J=1.9Hz, 1H) .

[0041] 13 C NMR (126MHz, dmso) δ175.09, 165....

Embodiment 3

[0042] Embodiment 3: The synthetic route of flavonoid derivative YSW-02 is as follows:

[0043]

[0044]Flavonoid derivatives b (678mg, 1mmol), acetylsalicylic acid c (216mg, 1.2mmol), DMAP (183mg, 1.5mmol) were added to a 100ml one-port bottle, 25ml DMF was added, the system was in suspension, and EDCI (287mg, 1.5mmol), after 1-2 hours, the system was slowly dissolved, stirred overnight at room temperature for 14h, and the reaction was detected by TLC. After the basic reaction of the raw materials was complete, the system was poured into water, and a yellow solid was precipitated, filtered by suction, and purified by column chromatography to obtain Yellow solid 500 mg, yield 59.5%.

[0045] 1 H NMR (500MHz, dmso-d 6 )δ12.12(s, 1H), 8.18(d, J=7.8Hz, 1H), 7.68(d, J=8.6Hz, 1H), 7.50(d, J=7.5Hz, 2H), 7.46-7.20( m, 21H), 7.16(t, J=7.6Hz, 1H), 6.98(s, 1H), 6.61(d, J=1.7Hz, 1H), 5.30(s, 2H), 5.23(s, 2H), 4.99(s, 2H), 4.96(s, 2H), 2.30(s, 3H).

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Abstract

The invention provides flavonoid derivatives and a preparation method thereof and an application in preparation of an immunoenhancer. The flavonoid derivatives have a structure of a general formula (I), and the synthesis method of the flavonoid derivatives comprises the following steps: o-benzyloxybenzoic acid a or acetylsalicylic acid c and a benzyl-protected compound b are subjected to a condensation reaction under the action of a base to prepare the flavonoid derivatives YSW-01 and YSW-02; and the flavonoid derivatives YSW-01 and YSW-02 are subjected to benzyl group removal under the catalysis action of palladium carbon to obtain the flavonoid derivatives YSW-TM1 and YSW-TM2. The experiments prove that the flavonoid derivatives provided by the invention have the effect of promoting T cell proliferation. The invention also provides the application of research and development of the compound in preparation of the immunoenhancer.

Description

Technical field: [0001] The invention belongs to the field of medicine, and relates to a flavonoid derivative and its preparation method and its application in the preparation of immune enhancer Background technique: [0002] T cells are the main component of lymphocytes. After contacting antigens, T cells are stimulated and activated by double signals, and then undergo clonal expansion and differentiation into effector T cells, thereby exerting the function of cellular immunity. Therefore, proliferation is a key link in the functioning of T cells and plays a vital role in the immune response. Immunopotentiators that promote T cell proliferation can provide new strategies for the treatment of immunodeficiency diseases and tumor immunity. Immunodeficiency diseases increase the probability of patients suffering from infectious diseases, the incidence of malignant tumors or the metastasis / recurrence rate of cancer cells are greatly increased. Patients with malignant tumors of...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61P37/04
CPCA61P37/04C07D311/30
Inventor 张良何增国邢严李文保杨萌琳汤伟管华诗
Owner OCEAN UNIV OF CHINA
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