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Two NK007 optical pure isomers and synthesis and application thereof

A technology of optical isomers and isomers, applied in applications, botany equipment and methods, chemicals for biological control, etc., can solve problems such as increased transportation and storage costs, strong odor, and environmental pollution, and achieve Good effect on regulating immune activity

Active Publication Date: 2016-04-06
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the synthesis of phenanthrene acid 5 to phenanthrene benzyl alcohol 6 and the synthesis of 10 to 11 all use aluminum tetrahydrogen lithium, which is costly and has a potential explosion hazard in industrial mass production
The oxalyl chloride used in the process from 8 to 9 is highly volatile, has a strong odor during operation, pollutes the environment, and increases transportation and storage costs

Method used

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  • Two NK007 optical pure isomers and synthesis and application thereof
  • Two NK007 optical pure isomers and synthesis and application thereof
  • Two NK007 optical pure isomers and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of Compounds 6, 9a, 11a and Compound NK007-1, Compound NK007-2

[0038] Compound 6 (such as image 3 shown)

[0039] N 2 Under protection, 150 mL of freshly distilled anhydrous THF was added to a 250 mL reaction flask, and 1.14 g (0.03 mol) of NaBH was added in batches at room temperature. 4 6.84 g (0.02 mol) of raw material 5 was added in batches under electromagnetic stirring, stirred for 10 minutes, 6.99 g (0.03 mol) of zirconium tetrachloride was slowly added, stirred at room temperature for 10 hours, and the reaction of raw materials was detected by TLC. Add 10mL of water and 10mL of dilute hydrochloric acid dropwise under cooling in an ice-water bath to fully decompose excess NaBH 4 , after precipitation with 250mLCH 2 Cl 2 Dilute with 50mL of water, stir and separate, the organic phase is washed with water, washed with saturated brine, anhydrous MgSO 4 Drying and desolvation gave 6.46 g of a white solid product with a yield of 95%. Mel...

Embodiment 2

[0049] Embodiment 2: the anti-tobacco mosaic virus activity (table 2) of compound NK007-1 and NK007-2

[0050] 1. Virus purification and concentration determination:

[0051] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the crude virus extract was centrifuged twice with polyethylene glycol, the concentration was measured and refrigerated at 4°C for later use.

[0052] 2. Compound solution preparation:

[0053] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL mother solution, and then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparation was directly diluted with water.

[0054] 3. In vitro effect:

[0055] Rub inoculation of leaves of Shanxi tobacco at the right age, rinse with running water, the virus concentration is 10 μ...

Embodiment 3

[0068] Example 3: Modulating immune activity of compounds NK007-1 and NK007-2

[0069] testing method

[0070]Materials: 2 sets of surgical scissors, 2 sets of ophthalmic forceps, glass slides, 96-well plate (Corning Company), pipette, 40 μm cell strainer, 15 mL centrifuge tube (BD Company), EP tube, counting plate, microscope, centrifuge, discharge gun, Babl / c mice (Victorian Liver). Reagents: PBS (Beijing Suo Lai Bao Company), RPMI-1640 medium and DMEM medium (Gibco Company), serum (Gibco Company), erythrocyte lysate (Beijing Suo Lai Bao Company), LPS (Sigma Company); Trypan blue. Double antibody (Beiyuntian Company) (1) Effect of optical isomers on the production of TNF-α in splenocytes stimulated by LPS

[0071] Steps:

[0072] 1) Configuration of various solutions: NK007 optical isomer mother solution is 1mM;

[0073] LPS: 1mg / mL;

[0074] Complete medium: 1640+10% serum+1% double antibody.

[0075] 2) Preparation of splenocyte suspension:

[0076] 1. Rat killing ...

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Abstract

The invention relates to two optical pure isomers called NK007 for short, synthesis thereof and application thereof in the aspects of plant virus resistance and immunoregulatory activity. Compounds NK007-1 and NK007-2 have good anti-tobacco-mosaic-virus activity, and can be used for treating plant virus diseases. The compounds NK007-1 and NK007-2 have good immunoregulatory activity and can be used for preparing medicine treating rheumatic arthritis. The method for testing the immunoregulatory activity of the compounds can be used for screening novel arthritis medicine. Please see the chemical structural formulae of the compounds in the specifications.

Description

technical field [0001] The present invention relates to two optically pure isomers of NK007 for short, their synthesis and their application in anti-plant virus and regulation of immune activity. Background technique [0002] The structural formula of the compound referred to as NK007 is: [0003] [0004] Chirality is a basic feature of life processes, macromolecules as an important basis for life activities. Such as nucleic acids, proteins, polysaccharides, etc. all have chirality: when a chiral drug enters a living body, its two enantiomers usually exhibit different biological activities. Due to the lack of awareness of this, human beings have learned a painful lesson before. For example, a drug developed by a German pharmaceutical company in the 1950s to treat the early discomfort of pregnant women—the drug was very effective, but it was soon discovered that many babies born to pregnant women who took the drug had mutilated limbs. Later, it was found that one confi...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07C51/41C07C59/245A01N43/90A61K31/437A61P37/02A61P29/00A61P19/02A01P1/00G01N33/68
CPCA01N43/90A61K31/437C07C51/41C07C59/245C07D471/04G01N33/68C07B2200/07G01N33/6869G01N2800/24
Inventor 汪清民尹芝南王兹稳洪章勇刘玉秀温倜宋红健郑彦龙
Owner NANKAI UNIV
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