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A thiazolidinone compound and its application in the preparation of medicines for treating diseases related to iron disorders
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A thiazolidinone class, the technology of said thiazolidinone is applied in thiazolidinone derivatives and their application fields, and can solve the problems of hearing impairment, easy to cause infection, liver damage and the like
Active Publication Date: 2016-04-20
SHANDONG UNIV
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Embodiment 1
[0043] Preparation of 2-(2-chlorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4-one
[0044]
[0045] by HCl:H 2 The ratio of O (1:4) is dubbed hydrochloric acid solution. Weigh 11.4g (150mmol) of ammoniumthiocyanate and dissolve it in 50mL of hydrochloric acid solution, add 10.5mL (100mmol) of 3-toluidine, heat to 85°C under stirring conditions, the mixture becomes clear, after 12 hours of reaction, TLC monitors the reaction, After the reaction, the mixture was cooled to room temperature, and a viscous oily liquid appeared, which was extracted with ethyl acetate, and the extract was washed with 10% hydrochloric acid solution, saturated sodiumchloride solution, and water successively, and the solvent was evaporated off the extract under reduced pressure to obtain 2-Tolylthiourea.
[0046] Add 996mg (6.0mmol) of 2-tolylthiourea and 2479mg (30mmol) of anhydroussodium acetate into 20mL of ethanol, add 1.28mL (12mmol) of ethyl chloroacetate under stirring co...
[0051] The preparation method is similar to the preparation of the compound of Example 1.
[0052] The product is a yellow powder with a yield of 75.5%; 1 HNMR (400MHz, CDCl 3 )δ(ppm)=8.0(s,1H),7.85(m,2H),7.72(s,1H),7.45(m,9H),4.12(d,2H).C 23 h 15 ClN 2 OS,ESI-MS:m / z403.7(M+1) + .
[0055] The preparation method is similar to the preparation of the compound of Example 1.
[0056] The product is an orange powder with a yield of 92.6%; 1 HNMR (400MHz, CDCl 3 )δ(ppm)=8.2(s,1H),7.72(s,1H),7.49(d,1H),7.35(m,7H),2.53(s,3H).C 17 h 13 ClN 2 OS 2 ,ESI-MS:m / z360.0(M+1) + .
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Abstract
The invention discloses a thiazolidone compound, wherein a chemical structure of the thiazolidone compound is shown in a general form (I). The invention also discloses application of the thiazolidone compound in preparation of a medicine used for treating thalassemia. Experiments prove that the thiazolidone compound can be used for effectively stimulating expression of hepcidin in cells under the condition that concentration is 10mu M, can be still used for effectively inducing expression of hepcidin in liver when being exposed for 6 hours, 24 hours and 48 hours respectively at a dosage of 30mg / kg in animal level and can be also used for effectively reducing level of serum iron, so that the thiazolidone compound can take hepcidin as a target, can be used for reducing iron level in serum, is hopeful to be a potential medicine used for treating and alleviating iron disorder-related diseases and has a broad clinical application prospect and a great economic development value.
Description
technical field [0001] The invention relates to thiazolidinone derivatives and applications thereof, in particular to a novel thiazolidinone compound and its application in the preparation of medicines for treating diseases related to iron disorders; it belongs to the field of medicinal chemistry. Background technique [0002] Iron is an essential trace element for the body, and it is widely involved in the physiological processes of the body, such as electron transfer, DNA replication, DNA repair, etc. In some diseases, such as β-thalassemia, hereditary hemochromatosis, hepatitis C, alcoholic liver disease, renal hyperfunction, etc., are accompanied by high serumiron levels and low hepcidin expression levels symptom. [0003] β-thalassemia is a kind of disease that seriously threatens human health. It has a high incidence in my country, especially in Guangdong, Guangxi, Guizhou, Hainan and other provinces, and frequently occurs in Southeast Asia and countries around the M...
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