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Thiazolidone derivates and application thereof in preparing anti-lung cancer medicine

A thiazolidinone class, the technology of said thiazolidinone, which is applied to novel thiazolidinone derivatives and its application field in the preparation of anti-lung cancer drugs, can solve the toxicity, cannot be used for the treatment of stubborn drug-resistant or recurrent tumors, Problems such as poor outcomes in treating cancer patients

Inactive Publication Date: 2009-03-11
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] With the continuous advancement of science and technology, especially the emergence of high-throughput screening systems and combinatorial chemistry, and the continuous emergence of new anticancer drugs with the assistance of computer chemistry, the treatment of tumors has made great progress. Oncology Patient Outcomes Remain Poor
For most cancer patients, current treatments are only short-acting, and current anticancer drugs often lead to drug resistance or intolerable toxicity
Because chemotherapeutic drugs are often given to patients at the maximum dose that the patient can tolerate, dose escalation eventually leads to unacceptable toxicity, so it cannot be used to treat refractory drug-resistant or recurrent tumors

Method used

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  • Thiazolidone derivates and application thereof in preparing anti-lung cancer medicine
  • Thiazolidone derivates and application thereof in preparing anti-lung cancer medicine
  • Thiazolidone derivates and application thereof in preparing anti-lung cancer medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of 2-(2-chlorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4-one

[0054]

[0055] by HCl:H 2 The ratio of O (1:4) is dubbed hydrochloric acid solution. Weigh 11.4g (150mmol) of ammonium thiocyanate and dissolve it in 50mL of hydrochloric acid solution, add 10.5mL (100mmol) of 2-chloroaniline, and 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 sodium chloride solution, and water successively, and the solvent was evaporated off the extract under reduced pressure to obtain 2-Chlorophenylthiourea.

[0056] Add 1120mg (6.0mmol) of 2-chlorophenylthiourea and 2479mg (30mmol) of anhydrous sodium acetate into 20mL of ethanol, add 1.28mL (12mmol) of ethyl chloroac...

Embodiment 2

[0060] 2-(2-Chlorophenylimino)-5-(4-methoxybenzylidene)-1,3-thiazol-4-one

[0061]The preparation method is similar to the preparation of the compound of Example 1.

[0062] The product is a yellow powder with a yield of 73.9%; 1 H NMR (400MHz, MeOD): δ (ppm) = 7.53 (s, 1H), 7.38 (d, 1H, J = 8.0), 7.32 (d, 2H, J = 8.4), 7.23 (t, 1H, J = 7.6), 7.09(t, 1H, J=7.6), 6.98(d, 1H, J=7.4), 6.89(d, 2H, J=8.4), 3.72(s, 3H), 1.91, 1.19(ss, 1H ); ESI-MS: m / z 345.6 (M+1) + .

Embodiment 3

[0064] 2-(2-Chlorophenylimino)-5-(2-naphthylidene)-1,3-thiazol-4-one

[0065] The preparation method is similar to the preparation of the compound of Example 1.

[0066] The product is an orange powder with a yield of 99.0%; 1 H NMR (400MHz, MeOD): δ (ppm) = 8.30 (s, 1H), 8.04 (d, 1H, J = 8.1), 7.82 (d, 2H, J = 4.1), 7.49 (m, 3H), 7.37 (dd, 2H, J=7.8), 7.19(t, 1H, J=7.4), 7.06(t, 1H, J=7.6), 6.96(d, 1H, J=7.9), 1.91, 1.18(ss, 1H ); ESI-MS: m / z 365.6 (M+1) + .

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Abstract

The invention discloses a thiazolidone compound the chemical structure of which is shown by a general formula (I). The compound can selectively kill lung cancer cells and drug-resistant lung cancer cells which are over-expressed by P-glycoprotein, and have no obvious toxity on normal fibroblasts. The compound is a novel compound for starting an apoptotic signal transfer mechanism of tumor cells, is a potential anti-lung cancer medicine for selectively inducing apoptosis of the lung cancer cells and effectively treating refractory lung cancer, and has wide market application prospect.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, more specifically to a class of novel thiazolidinone derivatives and their application in the preparation of anti-lung cancer drugs. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. The mortality rate caused by cancer is second only to cardiovascular disease among all diseases. Over the past few decades, tumor treatment methods have been greatly developed, including surgical treatment, radiotherapy and chemotherapy, among which chemotherapy plays a very important role, and there are various types of anticancer drugs. Anticancer drugs can be roughly divided into three categories according to their action principles: drugs that directly act on DNA and destroy its structure and function; drugs that interfere with DNA and nucleic acid synthesis; drugs that affect protein synthesis. [0003] In recent years, due to the...

Claims

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Application Information

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IPC IPC(8): C07D277/54A61K31/426A61P35/00
Inventor 闫兵周宏钰张斌翟淑梅张秋吴书泓方炳良
Owner SHANDONG UNIV
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