Rhein specific group modified organic compound, aryl metal complex, preparation method and application thereof

A technology of organic compounds and metal complexes, applied in the field of medicine, can solve the problems of FTO inhibitor research reports without metal complexes, achieve high anti-cancer effects, inhibit FTO activity, and increase active oxygen

Active Publication Date: 2018-09-14
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no research report on FTO inhibitors of metal complexes

Method used

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  • Rhein specific group modified organic compound, aryl metal complex, preparation method and application thereof
  • Rhein specific group modified organic compound, aryl metal complex, preparation method and application thereof
  • Rhein specific group modified organic compound, aryl metal complex, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Under argon atmosphere, rhein (0.14g, 0.5mmol), EDCI (1.05g, 5.5mmol), HOBt (0.61g, 4.5mmol) and the bridging ligand 4-(4'-methyl-2, 2'-Bipyridyl)-methylamine (1.0g, 5.0mmol) was dissolved in DMF (N,N-dimethylformamide), and 100 μL of TEA (triethylamine) was added dropwise, and stirred for 5 h under ice bath, The crude product was separated and purified by column chromatography to obtain the organic compound L1 modified by the bridging ligand with a yield of 55%.

[0035] 1 H NMR (400Hz, d 6 -DMSO): 11.93(s,2H), 9.66(t,1H), 8.63(d,1H), 8.52(d,1H), 8.38(s,1H), 8.23(m,2H), 7.85(dd, 2H) 7.77 (d, 1H), 7.42 (t, 2H), 7.28 (d, 1H), 4.63 (d, 2H), 2.42 (s, 3H).

[0036] The preparation method of the above-mentioned bridging ligand 4-(4'-methyl-2,2'-bipyridine)-methylamine is as follows: step (1): SeO 2 (selenium dioxide), 1,4-dioxide (1,4-dioxane), 4,4'-dimethyl-2,2'-bipyridyl (4,4'-dimethyl-2,2'- bipyridyl) mixed in a three-necked flask, reflux heating reaction 0.4-45h, af...

Embodiment 2

[0040] Under argon atmosphere, organic compound L1 (0.05g, 0.1mmol) was mixed with [Ru(η 6 -p-cymene)Cl 2 ] 2 (0.31g, 0.5mmol) was dissolved in methanol, reflux reaction at 65°C for 2h, and NH 4 PF 6 , frozen at -4°C for 1 h, and centrifuged to obtain complex 1 with a yield of 65%.

[0041] 1 H NMR (400Hz, d 6 -DMSO):9.72(s,1H),9.44(d,1H),9.36(d,1H),8.60(s,1H),8.51(s,1H),8.17(s,1H),7.90(s, 1H)7.81(m,1H),7.74(d,1H),7.66(dd,2H),7.41(d,1H),6.19(d,2H),5.94(d,2H),4.75(d,2H) , 3.17(s,2H), 2.59(s,3H), 2.33(m,1H), 2.15(s,3H), 0.95(d,6H). ESI-MS(+): theoretical value: [1-PF 6 - ] + m / z: 736.20, experimental value: m / z 736.25.

Embodiment 3

[0043] Under argon atmosphere, organic compound L1 (0.05g, 0.1mmol) was mixed with [Ru(η 6 -p-cymene)I 2 ] 2 (0.489g, 0.5mmol) was dissolved in methanol, and refluxed at 65°C for 2h. After the reaction, ether was added and centrifuged to obtain complex 2 with a yield of 75%.

[0044] 1 H NMR (400Hz, d 6 -DMSO):11.95(s,2H),9.68(s,1H),9.40(d,1H),9.32(d,1H),8.61(s,1H),8.54(s,1H),8.25(s, 1H)7.88(dd,2H),7.79(d,1H),7.64(dd,2H),7.45(d,1H),6.13(d,2H),6.00(d,2H),4.78(d,2H) ,2.72(m,1H),2.60(s,3H),2.39(s,3H),0.99(d,6H). ESI-MS(+): theoretical value: [2-I - ] + m / z 828.65, experimental value: m / z 828.17.

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Abstract

The invention discloses a rhein specific group modified organic compound, an aryl metal complex, a preparation method and application thereof. Compared with rhein molecules, the organic compound and metal complex have better antitumor and antibacterial activity, and the metal complex also can induce nucleic acid configuration transformation. Specifically, the aryl metal dimer and the above-mentioned metal complex both have good FTO (fat mass and obesity associated) inhibitory activity, and are good FTO inhibitors. The invention also discloses a synthesis method of the organic compound and themetal complex thereof, and the method has the characteristics of simple technological process, easy operation, and high yield. Finally, the invention discloses application of the rhein group-containing organic compound, the metal complex and aromatic metal dimer thereof in preparation of FTO inhibitor drugs, FTO inhibitor drug components, weight-reducing drugs, weight-reducing drug components, anticancer drugs, anticancer drug components, antibacterial drugs and antibacterial drug components.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to an organic compound modified by a specific group of rhein, a metal complex thereof, a preparation method and an application thereof. technical background [0002] Cancer is one of the most serious diseases threatening human life. According to the data released by the World Health Organization, it is estimated that by 2020, there will be 15 million new cancer patients worldwide every year. Most platinum-based and other drugs currently used clinically have the disadvantages of high toxicity, poor selectivity, and drug resistance. Therefore, research and development of new high-efficiency, low-toxicity anticancer drugs has become an urgent task. With the in-depth study of the mechanism of action of anticancer drugs in tumor cells, many metal anticancer drugs with potential medicines have emerged in recent years. Among them, aryl metal compounds have been found to have good anticancer activity....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/40C07D213/75C07D233/61C07F15/00A61K31/555A61K31/417A61P35/00A61P3/04A61P31/04
CPCA61P3/04A61P31/04A61P35/00A61K31/417A61K31/555C07D213/40C07D213/75C07D233/61C07F15/0026C07F15/004C07F15/0053C07F15/008
Inventor 刘红科孔亚琼钱勇苏志李季吴健
Owner NANJING NORMAL UNIVERSITY
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