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2-vinyl-8-hydroxyquinoline derivative, preparation method and application thereof

A hydroxyquinoline and vinyl technology, which is applied in the field of preparation of organic compounds, can solve problems such as slow expansion speed, and achieve the effects of simple preparation, easy preparation and promotion of stem cell proliferation.

Inactive Publication Date: 2008-05-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although bone marrow samples are easy to obtain, the content of mesenchymal stem cells is relatively small, accounting for about 1 / 100,000 of mononuclear cells in bone marrow; and the expansion speed is slow, which has also become the cause of many major human diseases (such as nerve injury, neurodegeneration). disease, heart injury, osteoporosis, aplastic anemia, etc.)

Method used

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  • 2-vinyl-8-hydroxyquinoline derivative, preparation method and application thereof
  • 2-vinyl-8-hydroxyquinoline derivative, preparation method and application thereof
  • 2-vinyl-8-hydroxyquinoline derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 2″-[2′-5-(2-methyl-8-hydroxyquinoline)-vinyl]-8″-hydroxyquinoline (Compound 1)

[0027] Weigh 2.340g 2-methyl-5-formyl-8-hydroxyquinoline and 1.790g 2-methyl-8-hydroxyquinoline, dissolve in 35mL acetic anhydride, stir to make it completely dissolved, in N 2 Under protection, heat and reflux for 40h at 130°C. During the reaction, the reaction was monitored by thin-layer chromatography. The reaction was completed and cooled to room temperature. Then the reaction mixture was poured into 50 mL of ice water, stirred for 3 to 4 hours, and the supernatant was poured out to obtain a brown-black viscous shape. After precipitation, silica gel column chromatography was performed using petroleum ether / ethyl acetate (V:V=9:1) as the eluent to obtain 1.325 g of the pure target product with a yield of 32.3%. m.p.187~189℃. Rf=0.45(V 石油醚 / V 乙酸乙酯 =3:1). ESI-MS m / z: 329.4 (M+H). IR(KBr)v(cm -1 ): 3410.37, 2925.50, 1631.78, 1592.55, 1501.37, 1462.00, 1202.20, 1181.52. 1 H NMR(CD...

Embodiment 2

[0029] Preparation of 2″-[2′-3-(1-hydro-indole)-vinyl]-8″-hydroxyquinoline (compound 2)

[0030] Weigh 0.795g 2-methyl-8-hydroxyquinoline and 0.725g 3-formylindole, dissolve in 20mL acetic anhydride, 2 Under protection, the reaction was refluxed with magnetic stirring at 125°C for 40h. After cooling, the reaction mixture was poured into 250 mL of ice water and stirred overnight. The resulting brown precipitate was washed with distilled water, and then petroleum ether / ethyl acetate (V:V=8:1) was used as eluent for silica gel column layer Analysis and separation yielded 0.61 g of 2"-[2'-3-(1-acetyl-indole)-vinyl]-8"-hydroxyquinoline acetate with a yield of 32.8%. m.p.194~196℃. UV(DMF)λmax: 306 nm, 361nm. 1 H NMR(CDCl 3 , 400MHz) δppm: 2.577 (s, 3H), 2.686 (s, 3H), 7.425 (m, 4H), 7.670 (m, 3H), 7.817 (d, J=16.4Hz, 1H), 7.958 (d, J =7.6 Hz, 1H), 8.134 (d, J=8.4 Hz, 1H), 8.483 (d, J=7.6 Hz, 1H). IR(KBr)v(cm -1 ): 3050.34 (CH stretching vibration on aromatic ring); 1746.05, 1641.81 (C=O...

Embodiment 3

[0033] Preparation of 2″-[2′-2-(1-methyl-benzimidazole)-vinyl]-8″-hydroxyquinoline (Compound 3)

[0034] 0.795 g 2-methyl-8-hydroxyquinoline and 0.80 g 1-methyl-2-formyl-benzimidazole were dissolved in 20 ml of acetic anhydride, and under the protection of nitrogen, the reaction was refluxed with magnetic stirring at 130° C. for 48 h. After cooling, pour into 250ml of ice water and stir overnight to obtain a yellow precipitate. After washing with distilled water, perform silica gel column chromatography with petroleum ether / ethyl acetate (V:V=3:1) as the eluent to obtain the target product 0.692g , The yield is 46%. m.p.207~208℃. UV(DMF) λmax: 321nm, 367nm. 1 H NMR (CDCl3, 400MHz) δppm: 8.183 (d, J = 8.4 Hz, 1H), 8.128 (d, J = 15.2 Hz, 1H), 7.890 (d, J = 16.0 Hz, 1H), 7.817 (m, 1H) ), 7.618(d, J=8.4Hz, 1H), 7.455(t, J=7.6Hz, 1H), 7.392(m, 1H), 7.333(m, 3H), 7.207(d, J=8.8Hz, 1H) ), 1.591 (S, 3H). IR(KBr)v(cm -1 ): 34 07.75 (O-H stretching vibration); 1637.87 (C=C bond stretching v...

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Abstract

The invention discloses a 2-vinyl-8-bioquin derivative, which preparation method comprises that 2-bioquin-8-bioquin and aromatic aldehyde are added into acetic anhydride to be dissolved, heated, refluxed and reacted at 120-140DEG C for 40-96h, the reaction product is separated and purified via column chromatography to obtain the pure 2-vinyl-8-bioquin derivative. The inventive 2-vinyl-8-bioquin derivative has significant oxidization resistance, better than strong antioxidant glutathione GSH which can eliminate free group. The inventive product can be used to prepare antioxidant, which further can accelerate the increment of mesenchymal stem cells in bone marrow, to prepare bone marrow mesenchymal increment accelerant.

Description

Technical field [0001] The invention belongs to the field of preparation of organic compounds having antioxidant activity and promoting stem cell proliferation, and particularly relates to 2-vinyl-8-hydroxyquinoline derivatives, a preparation method thereof, and their application as antioxidants and bone marrow stem cell proliferation promoters. Background technique [0002] The British Harman put forward the theory of free radicals in 1956. He believed that free radicals attacked life macromolecules and caused tissue cell damage, which is the root cause of body aging and also an important cause of malignant diseases such as tumors. Free radicals in the human body are divided into oxygen free radicals and non-oxygen free radicals. Oxygen free radicals dominate, accounting for about 95% of the total free radicals. Oxygen free radicals include superoxide anions (O 2 - ·), hydrogen peroxide molecule (H 2 O 2 ), hydroxyl radical (OH·), hydroperoxy (HO 2 - ·), alkoxy peroxy (ROO·), ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C07D215/26C07D409/06A61K31/4709A61P39/06A61P43/00
Inventor 曾和平王婷婷
Owner SOUTH CHINA UNIV OF TECH
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