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Selenourea derivatives, pharmaceutical compositions and uses thereof

The technology of a composition and a medicine is applied in the field of preparing the selenourea derivatives, and can solve the problems of unsatisfactory curative effect, drug resistance and the like

Active Publication Date: 2020-05-01
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the curative effect of many drugs in cancer treatment is not ideal, and drug resistance and other problems are still needed. Compounds with novel structures and anti-tumor effects through various mechanisms are still needed. These compounds have significant anti-tumor cell proliferation and induction of tumor cell apoptosis. Activity, very significant activity on drug-resistant tumor cells, providing new therapeutic drugs and strategies for tumor treatment

Method used

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  • Selenourea derivatives, pharmaceutical compositions and uses thereof
  • Selenourea derivatives, pharmaceutical compositions and uses thereof
  • Selenourea derivatives, pharmaceutical compositions and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] Example 1: N-methyl-2-bis(pyridin-2 base)methyleneamino-selenourea

[0150] Step 1. S-Methylthio 4-methyl-3-thiosemicarbazide

[0151] Add 0.423g (4mmol) 4-methyl-3-thiosemicarbazide, 10ml absolute ethanol and 0.568g (4mmol) methyl iodide to a 50ml single-necked bottle, and react under reflux at 85°C for one hour to obtain S-methylthio 4 -The ethanol solution of methyl-3-thiosemicarbazide was cooled, solids were precipitated, and the solvent was spin-dried to obtain S-methylthio-4-methyl-3-thiosemicarbazide as a solid (0.43g, 90%).

[0152] Step 2. 4-Methyl-3-selenocarbazide

[0153] Add 0.42g (4mmol) of sodium carbonate to the newly prepared sodium selenate 0.41g (4mmol) ethanol (10ml) solution, and add 0.54g (4mmol) of S-methylthio 4-methyl-3-thiosemicarbazide ) solid was added to the ethanol solution of sodium hydrogen selenate, and reacted at room temperature for 20h to generate 4-methyl-3-selenacarbazide (0.49g, 80%).

[0154] After the reaction is completed, ad...

Embodiment 2

[0157] Example 2: 2-bis(pyridin-2 base)methyleneamino-selenourea

[0158] Method is with embodiment 1, intermediate selenaminocarbazide, 1 H-NMR (400MHz, DMSO) δppm: 4.521 (s, 2H), 7.644 (m, 1H), 7.985 (m, 1H), 9.082 (d, 1H), the product is yellow solid 2-di(pyridin-2yl) Methyleneamino-selenourea 1 H-NMR (400MHz, DMSO) δppm: 7.477-7.495 (m, 1H), 7.523-7.543 (d, 1H), 7.606-7.625 (m, 1H), 7.933-7.957 (m, 1H), 7.990-8.013 ( m, 1H), 8.324~8.345(d, 1H), 8.562~8.572(d, 1H), 8.828~8.839(d, 1H), 8.921(d, 1H), 9.272(d, 1H), 13.275(s, 1H) , HLPC-MS m / z: 306.1[M+1] + .

Embodiment 3

[0159] Example 3: N-allyl-2-bis(pyridin-2 base)methyleneamino-selenourea

[0160] Method is with embodiment 1, intermediate 4-allyl-3-selenocarbazide 1 H-NMR (400MHz, DMSO) δppm: 4.139 (m, 2H), 4.529 (m, 2H), 5.074~5.142 (m, 2H), 5.829~5.872 (m, 1H), 8.208 (m, 1H), 9.150 (m, 1H), product N-allyl-2-bis(pyridin-2yl)methyleneamino-selenourea, yellow solid 1 H-NMR (400MHz, DMSO) δppm: 4.3296~4.3584 (m, 2H), 5.1507~5.2222 (m, 2H), 5.8968~5.9396 (m, 1H), 7.4949~7.5299 (m, 2H), 7.6112 (m, 1H), 7.9706~8.0056 (m, 2H), 8.2648~8.2844 (d, 1H), 8.5801~8.5920 (d, 1H,) 8.8295~8.8421 (d, 1H), 9.4460~9.4754 (m, 1H), 13.5766 ( s, 1H). HLPC-MSm / z: 346.2[M+1] + .

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PUM

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Abstract

The invention relates to a selenosemicarbazone derivative, and a pharmaceutical composition and an application thereof. Specifically, the invention relates to a compound shown as a formula I or an isomer thereof, a pharmaceutically acceptable salt, a composition comprising the compound shown as the general formula I or the isomer thereof, the pharmaceutically acceptable salt and a pharmaceutically acceptable vector, and applications of the compound shown as the general formula I or the isomer thereof and the pharmaceutically acceptable salt in preparing drugs for resisting tumor or treating diseases or symptoms related to the tumor. The formula I is shown in the description.

Description

technical field [0001] The present invention relates to selenourea semicarbazone derivatives. This type of compound has significant activity of anti-tumor cell proliferation and induction of tumor cell apoptosis, and has very significant activity against drug-resistant tumor cells. The present invention also relates to a method for preparing the selenasesemicarbazone derivatives, a pharmaceutical composition containing the selenosesemicarbazone derivatives, and the use of the selenosesemicarbazone derivatives as antitumor drugs or for antitumor applications. Background technique [0002] A tumor is a developing or mature normal cell in the human body. Under the long-term action of certain adverse factors, a certain cell group, a new organism formed by excessive proliferation or abnormal differentiation, forms a local tumor. However, it is different from normal tissues and cells. It does not grow according to the metabolism rules of normal cells, and becomes unconstrained and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/53C07D239/26A61K31/4402A61K31/505A61K31/517A61P35/00
CPCC07D213/53C07D239/26
Inventor 钟武李松黄亚飞周辛波肖军海李行舟郑志兵
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A