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Rhodanine derivative and preparation method thereof

A technology of derivatives and anti-tumor drugs, applied in the field of rhodanine derivatives and its preparation, can solve the problems of cytotoxicity, short half-life of sodium hydrosulfide, DNA damage of human lung fibroblasts, etc., and achieve good inhibitory effect and strong activity Effect

Inactive Publication Date: 2013-04-03
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Sodium hydrosulfide, an exogenous hydrogen sulfide donor, causes DNA damage in human lung fibroblasts by inducing the levels of downstream apoptotic proteins such as p21, Bax and cytochrome c, but not upregulating the levels of the anti-apoptotic protein Bcl-2 At the same time, the half-life of sodium hydrosulfide is very short, and it is toxic to cells, especially nerve cells, when the concentration is large, and 5-p-hydroxyphenyl-1,2-dithiole-3-thione is a slow Compounds that release hydrogen sulfide

Method used

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  • Rhodanine derivative and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) Add 0.494g, 2.0mmol of 2-[-4-oxo-2-thio-thiazolidin-3-yl]-4-methylpentanoic acid, 0.368g, 2.0mmol of p-bromobenzaldehyde and Add 0.313g and 4.1mmol of ammonium acetate to 20mL of toluene, heat and reflux for 1h, evaporate the solvent under reduced pressure, and perform column chromatography with eluent petroleum ether and ethyl acetate at a volume ratio of 4:1 to obtain a light yellow solid, the product The rate is 75.9%, and the melting point is 148.5~152.0°C. The hydrogen spectrum of the product Z-2-[5-(4-bromobenzylidene)-4-oxo-2-thio-thiazolidin-3-yl]-4-methylpentanoic acid 1 H NMR (400MHz, CDCl 3 ) δ: 0.94(d, 3H, J=6.6Hz, CH 3 ), 0.98(d, 3H, J=6.5Hz, CH 3 ), 1.48~1.61(m, 1H, CH), 2.08~ 2.16(m, 1H, CH 2 ), 2.25~2.32(m, 1H, CH 2 ), 5.79~5.80(m, 1H, CH), 7.35(d, 2H, J=8.4Hz, ArH), 7.62(d, 2H, J=8.0Hz,ArH), 7.63(s, 1H, =CH) .

[0020] (2) 495.576mg, 1.2mmol of Z-2-[5-(4-bromobenzylidene)-4-oxo-2-thio-thiazolidin-3-yl]-4-methylpentanoic acid , 299mg, 1.5mmol...

Embodiment 2

[0023] (1) Using p-bromobenzaldehyde and 2-(4-oxo-2-thio-thiazolidin-3-yl)-3-methylbutyric acid as raw materials, the preparation process is the same as step (1) of Example 1, A light yellow solid was obtained with a yield of 78.4% and a melting point of 157.9~160.1°C. The hydrogen spectrum of the product Z-2-[5-(4-bromobenzylidene)-4-oxo-2-thio-thiazolidin-3-yl]-3-methylbutanoic acid 1 H NMR (400MHz, CDCl 3)δ: 0.83(d, 3H, J=6.8Hz, CH 3 ), 1.27(d, 3H, J=6.3Hz, CH 3 ), 2.83~2.92(m, 1H, CH), 5.37(d, 1H, J=9.1Hz, CH), 7.35(d, 2H, J=8.4Hz, ArH), 7.62(d, 2H, J=8.4 Hz, ArH), 7.64(s, 1H, =CH).

[0024] (2) With Z-2-[5-(4-bromobenzylidene)-4-oxo-2-thio-thiazolidin-3-yl]-3-methylbutanoic acid and 5-p-hydroxybenzene Base-1,2-dithiole-3-thione was used as the raw material, and the preparation process was the same as step (2) of Example 1 to obtain a red solid with a yield of 73.4% and a melting point of 159.5~160.7°C. Product Z-2-[5-(4-bromobenzylidene)-4-oxo-2-thio-thiazolidin-3-y...

Embodiment 3

[0027] Using p-chlorobenzaldehyde and 2-(4-oxo-2-thio-thiazolidin-3-yl)-3-methylbutanoic acid as raw materials, the preparation process is the same as step (1) of Example 1 to obtain light Yellow solid, yield 80.3%, melting point 152.0~154.3°C. The hydrogen spectrum of the product Z-2-[5-(4-chlorobenzylidene)-4-oxo-2-thio-thiazolidin-3-yl]-3-methylbutanoic acid 1 H NMR (400MHz, CDCl 3 )δ: 0.87(d, 3H, J=6.6Hz, CH 3 ), 1.26(d, 3H, J=6.9Hz, CH 3 ), 2.84~ 2.93(m, 1H, CH), 5.37(d, 1H, J=9.0Hz, CH), 7.41~7.47(m, 4H, ArH), 7.66(s, 1H, =CH).

[0028] With Z-2-[5-(4-chlorobenzylidene)-4-oxo-2-thio-thiazolidin-3-yl]-4-methylbutanoic acid and 5-p-hydroxyphenyl-1 , 2-dithiole-3-thione was used as the raw material, and the preparation process was the same as step (2) of Example 1 to obtain a red solid with a yield of 70.1% and a melting point of 164.3~165.2°C. Product Z-2-[5-(4-chlorobenzylidene)-4-oxo-2-thioketothiazolidin-3-yl]-4-methylbutanoic acid 4-(3H-1,2-di Thiol-3-thiol-5-yl)...

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Abstract

The invention discloses a rhodanine derivative and a preparation method thereof, wherein the structure of the rhodanine derivative is shown in the specification; the preparation method comprises the following steps of: mixing a first rhodanine derivative of Bc1-2 inhibitor with an anti-tumour effect, 5-p-hydroxyphenyl-1,2-benzodithiole-3-thioketone, a condensing agent and alkali in a solvent according to the mass ratio of 1:(1-2):(1-2):0.001:0.1, reacting at 25-100 DEG C for 0.5-24 hours, and purifying, thereby obtaining the rhodanine derivative, wherein X comprises one of F, Br, Cl and Ph; R comprises one of CH2Ph, CH2CH(CH3)2 and CH(CH3)2; and the invention further relates to an anti-tumour drug composed of the rhodanine derivative and pharmaceutically acceptable carriers. By means of the manner, the prepared rhodanine derivative contains pharmacodynamic groups capable of releasing gas signal molecule hydrogen sulphide, is capable of generating anti-tumour synergistic effect, and has good inhibition effect on tumour cells; furthermore, the anti-tumour activity of the rhodanine derivative disclosed by the invention is stronger than that of the first rhodanine derivative before being modified.

Description

technical field [0001] The invention relates to the field of antitumor drugs, in particular to a rhodanine derivative and a preparation method thereof. Background technique [0002] Malignant tumors are one of the most threatening diseases to human beings. The annual global cancer death toll is about 7 million, 24% of which occur in China. At the same time, the cancer mortality rate in my country has been continuously increasing, but the survival rate of cancer patients in China and the cure The number of patients is only 13%, and cancer has become the number one killer that seriously threatens the health of our people. At present, the lesion and metastasis of cancer cells and the mechanism of action of drugs on cancer cells are still unclear, so the current treatment of tumors is still largely based on chemotherapy of anti-tumor drugs. However, chemical drugs have serious side effects and multi-drug resistance, which are always the biggest obstacles for human beings to defe...

Claims

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Application Information

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IPC IPC(8): C07D417/12A61K31/427A61P35/00
Inventor 敖桂珍楚小晶宋恒刘金宜王盼盼
Owner SUZHOU UNIV
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