Compound capable of selectively inducing Th2 immune cytokine production and potential application thereof

A technology of immune cells and compounds, applied in the fields of chemistry and medicine, can solve problems affecting Th1/Th2 selectivity

Pending Publication Date: 2019-04-19
RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, how the stability of α-GalCer / TCR or the stability of CD1d-α-GalCer / TCR affects Th1 / Th2 selectivity has not been reported

Method used

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  • Compound capable of selectively inducing Th2 immune cytokine production and potential application thereof
  • Compound capable of selectively inducing Th2 immune cytokine production and potential application thereof
  • Compound capable of selectively inducing Th2 immune cytokine production and potential application thereof

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Experimental program
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Embodiment Construction

[0028]

[0029] The following provides embodiments of the present invention (taking the above HU_ZHAO_2018-1 as an example):

[0030] Synthesis of compound 2:

[0031] At room temperature, mannose (1 eqv) was dissolved in acetone solution, a catalytic amount of iodine was added, the reaction was carried out at room temperature for 5 h, quenched with saturated sodium thiosulfate solution, evaporated to dryness, extracted with ethyl acetate and water, the organic phase was dried, and concentrated The crude product was obtained, the crude product was dissolved in tetrahydrofuran solution, solid potassium hydroxide (1.8eqv), catalytic amount of 18-crown-6, benzyl bromide (1.1eqv) were added successively, the reaction was carried out at room temperature for 30min, and saturated ammonium chloride solution was added. The reaction was quenched, extracted with ethyl acetate and water, the organic phase was dried, concentrated, and column chromatography gave Intermediate 2 in 80% ove...

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PUM

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Abstract

The invention relates to a preparation method of a novel glycoside ceramide analogue with immunoregulation activity and an application thereof, and belongs to the technical field of chemistry and medicine. Based on the structural analysis of a receptor and combined with molecular docking and molecular dynamics simulation technologies, a category of compound with modified sugar ring (tryptophan, glutamic acid derivative or p-hydroxyphenylpropionic acid are introduced into R1 or R2 sites respectively) is designed and synthesized. Biological activity research shows that such compound has Th2 selectivity and has potential for use in pharmaceuticals. The novel compound has the following main synthetic characteristics: R1 is a hydroxyl group or a tryptophan derivative linked through an amide condensation reaction; R2 is a hydroxyl group or an L-glutamic acid derivative linked through amide condensation reaction, or p-hydroxybenzoic acid; R3 is -OBn, R4 is -N3;or R3 is -N3, R4 is -OBn;R5 maybe a substituent such as SEt, S-iPr, SPh, STOL, OC (NH) CCl3, and the like.

Description

technical field [0001] The invention relates to a preparation method and application of novel glycoside ceramide analogs with immunomodulatory activity, and belongs to the technical field of chemistry and medicine. Background technique [0002] Takenori Natori et al in 1993 isolated a series of glycosphingolipids Agelasphins (α-galactosylceramides, α-Galcers), such as Agelasphins-9b, from spongy tissue in the sea near Okinawa, Japan, with strong anticancer activity. In 1995, Japan's Kyowa Hakko Kirin Company synthesized a series of Agelasphins-9b analogs to clarify the structure-activity relationship (SAR) of these compounds. KRN7000, as one of them, has a wide range of anti-virus, anti-tumor, anti-inflammatory and treatment of autoimmunity. Its high-efficiency immunomodulatory activity is the most eye-catching, and it is more convenient to synthesize (no hydroxyl group on the acyl fatty chain), and is considered to be the most ideal candidate for clinical application. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04C07H15/26C07H1/00A61P37/06A61K31/7056A61K31/7032
CPCA61P37/06C07H1/00C07H15/04C07H15/26
Inventor 杜宇国胡丽彦赵传芳
Owner RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI
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