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Alkannin derivatives as immune inhibitors and metal complexes thereof

A technology of metal complexes and immunosuppressants, applied in calcium organic compounds, zinc organic compounds, copper organic compounds, etc.

Inactive Publication Date: 2006-08-23
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the deficiencies and defects of the existing inventions, the present invention provides a shikonin derivative and its metal complex as an immunosuppressant, which solves the problem of immunosuppressants with stronger activity and lower toxicity, and synthesizes some Shikonin derivatives and metal ion complexes, their inhibitory and cytotoxic effects on immune cells were determined

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  • Alkannin derivatives as immune inhibitors and metal complexes thereof
  • Alkannin derivatives as immune inhibitors and metal complexes thereof
  • Alkannin derivatives as immune inhibitors and metal complexes thereof

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preparation example Construction

[0020] 1. Preparation of shikonin

[0021] CO 2 10 grams of supercritical extract, dissolved in 500ml of 0.2mol / l NaOH solution, stirred at room temperature for 24 hours, centrifuged to remove insoluble matter, combined supernatant, added 0.5mol / l H 2 SO 4 Solution until the solution turns red, put it aside for 2 hours, centrifuge to obtain a red precipitate, wash with water, and dry to obtain 5 g of shikonin crude product, recrystallize from petroleum ether to obtain 2.5 g of reddish-brown metallic luster crystals, yield 25% . Melting point 148-149°C, H-NMR (CDCl 3 )δ: 1.651, 1.755 (s, each 3H, 2CH 3 ), 2.311-2.387 (1H, m, -CHa), 2.623-2.660 (1H, m, -CHb), 4.911 (1H, d, J = 7.2, 4.0, -OCH-), 5.202 (1H, dd, J =8.0, 6.8, =CH-), 7.165 (s, 1H, Quin-H), 7.192 (2H, 2Ar-H), 12.494, 12.598 (each 1H, s, 2Ar-OH), consistent with literature reports (plant Acta Sinica, 1989, 31(7), 549-553).

[0022] 2. Preparation of shikonin ester derivatives

[0023] General method: take sever...

example

[0030] (1) Acetylshikonin copper complex: take 176mg of acetylshikonin, dissolve it in 3ml of acetone, and take another 194mg of copper acetate, dissolve it in 5ml of water, mix the two, place, precipitate out, filter, wash with a small amount of water, After drying, 229 mg of the complex was obtained, with a yield of 94.2%.

[0031] (2) Acetylshikonin zinc complex: Take 236mg of acetylshikonin, dissolve it in 5ml of acetone, and take another 263mg of zinc acetate, dissolve it in 5ml of water, mix the two, let it stand, precipitate out, filter, wash with a small amount of water, After drying, 309 mg of the complex was obtained, with a yield of 93.8%.

[0032] (3) Acetylshikonin calcium complex: Take 250mg of acetylshikonin, dissolve it in 5ml of acetone, and take another 240mg of calcium acetate, dissolve it in 8ml of water, mix the two, let it stand, precipitate out, filter, wash with a small amount of water, After drying, 298 mg of the complex was obtained, with a yield of ...

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Abstract

An alkannin derivative as immuno-suppressive agent and its metallic complex compound with a chemical constitution formulas III and IV disclosed in the specification, wherein in formula III, R is C1-6 saturated, unsaturated and aromatic acyl, in formula IV, R is hydrogen, C1-6 saturated, unsaturated and aromatic acyl, M is metallic Cu, Ca, Zn. The present invention realizes immunological suppression effect, thus can be used for treating diseases relating to human body autoimmune including chronic infectious arthritis, scleredema, lupus erythematosus, HIV infection and malignant tumor.

Description

technical field [0001] The invention relates to a shikonin derivative and its metal complex, in particular to a shikonin derivative and its metal complex as an immunosuppressant. Belongs to the field of medicine. Background technique [0002] Lishopermum eryhrorhizon is a traditional Chinese medicine, and its root is used for medicine. Sweet in taste, cold in nature, returns to Liver Meridian, has the function of cooling blood and promoting blood circulation, detoxifying and clearing rash. It is suitable for measles or febrile rash. Modern pharmacological studies have proved that comfrey has antibacterial, anti-inflammatory, and anti-tumor effects. Its main components are shikonin (shikoin I), acetylshikonin (Acetylshikonin II) and so on. [0003] [0004] After literature search, it was found that Xin Chen et al. published Shikonin, a component of antiinflammatory Chinese herbal medicine, selectively blocks chemokine binding to CC chemokinereceptor-1 (a traditional C...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/32C07F1/08C07F3/04C07F3/06
Inventor 李绍顺胡昆
Owner SHANGHAI JIAOTONG UNIV
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