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An organic compound modified by a specific group of rhein, its aryl metal complex, and its preparation method and application
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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, and achieve the effects of single reaction, good FTO activity, and increased reaction yield
Active Publication Date: 2021-07-27
NANJING NORMAL UNIVERSITY
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So far, there is no research report on FTO inhibitors of metal complexes
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Embodiment 1
[0035] Under argonatmosphere, 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%.
[0037] 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
[0041] Under argonatmosphere, 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%.
[0042] 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
[0044] Under argonatmosphere, 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%.
[0045] 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 an organic compound modified by a specific group of rhein and its metal complex, as well as its preparation method and application. Compared with rhein molecules, it has better antitumor and antibacterial activities. The metal complex also has Can induce nucleic acid conformational changes. Among them, the arylmetaldimer and the above-mentioned metal complexes all have good activity of inhibiting obesitygene FTO (Fat Mass and Obesity Associated), and are good FTO inhibitors. The invention also discloses a method for synthesizing the above-mentioned organic compound and its metal complex. The method has simple technological process, easy operation and high yield. Finally, the present invention discloses that the above-mentioned organic compounds containing rhein groups and their metal complexes and aryl metal dimers are used in the preparation of FTO inhibitor drugs, FTO inhibitor drug components, weight-loss drugs, weight-loss drug components, Applications in 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. [0002] technical background [0003] 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 a...
Claims
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