Platinum complex taking 2-benzoylpyridine thiosemicarbazone as ligand as well as synthesis method and application of platinum complex

A technology of benzoylpyridine thiosemicarbazone and benzoylpyridine, applied in the field of platinum complexes

Inactive Publication Date: 2020-12-15
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, platinum metalloid drugs have clinically serious adverse reactions, such as nephrotoxicity, bone marrow toxicity, ototoxicity, peripheral neurotoxicity, emetic effect and drug resistance

Method used

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  • Platinum complex taking 2-benzoylpyridine thiosemicarbazone as ligand as well as synthesis method and application of platinum complex
  • Platinum complex taking 2-benzoylpyridine thiosemicarbazone as ligand as well as synthesis method and application of platinum complex
  • Platinum complex taking 2-benzoylpyridine thiosemicarbazone as ligand as well as synthesis method and application of platinum complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of C1 platinum complex, the specific synthesis method is:

[0029] (1) Weigh 2-benzoylpyridine (1.83g, 10mmol) and place it in an EP tube containing 20mL of methanol, dissolve it ultrasonically, weigh thiosemicarbazide (0.91g, 10mmol) and add it to the above solution, then add 500μL of ice Acetic acid, put it in a 65°C oven after dropping, react for 1 day, the final solution color is orange and take it out; then when the temperature of the solution is not much different from room temperature, filter it into a 50mL beaker and place it in a fume hood to slowly volatilize , after a few days, light yellow crystals were precipitated, and the solution was filtered to obtain ligand L1;

[0030] Yield 73%. Anal. Calcd (%) for C13H12N4S: C, 60.91%; H, 4.72%; N, 21.86%; S, 12.51%. Found: C, 61.02%; H, 4.53%; N, 21.55% ;S,12.90%.IR(KBr,cm-1) 3303s,3134vs,3022m,1615s,1459s,1371s,1249s,955s,852s,782s,702s,699s,588s.MSI-MS:m / z=257.08for [M+H]+;

[0031] (2) Weigh the...

Embodiment 2

[0034] The synthesis of C2 platinum complexes, the specific synthesis method is:

[0035] (1) Weigh 2-benzoylpyridine (1.83g, 10mmol) and place it in a round-bottomed flask containing 20mL of methanol, stir to dissolve, weigh 4-methylthiosemicarbazide (1.05g, 10mmol) and add it to the above solution , then add 500 μL of glacial acetic acid, after the dropwise addition, stir and react at 65°C for 8 hours, the color of the solution is orange, take it out, filter it into a 50ml beaker, place it in a fume hood and volatilize slowly, after a few days, a light yellow crystal precipitates , filter the solution to obtain the ligand L2;

[0036] Yield 68%.Anal.Calcd(%)for C14H14N4S:C,62.20%;H,5.22%;N,20.72%;S,11.86%.Found:C,62.835%;H,5.045%;N,21.15% ;S,12.35%.IR(KBr,cm-1) 3296s,3054vs,2937m,1539s,1470s,1311s,1249s,1110s,1043s,818s,697s,649s,599s.MSI-MS:m / z=293.08for [M+Na]+;

[0037] (2) Weigh the ligand L2 (0.0135g, 0.05mmol) and Pt(DMSO) obtained in step (1) 2 Cl 2 (0.021 g, 0.0...

Embodiment 3

[0040] The synthesis of C3 platinum complexes, the specific synthesis method is:

[0041] (1) Weigh 2-benzoylpyridine (1.83g, 10mmol) and place it in a round-bottomed flask containing 20mL of methanol, stir to dissolve, weigh 4-phenylthiosemicarbazide (1.67g, 10mmol) and slowly add to the above Then add 500μL of glacial acetic acid, after the dropwise addition, stir and react for 8 hours at 65°C, the color of the solution is orange, take it out, and when the temperature of the solution is not much different from room temperature, filter it into a 50mL beaker and place in Slowly volatilize in the fume hood, and after a few days, light yellow crystals are precipitated, and the solution is filtered to obtain the ligand L3;

[0042] Yield 71%, Anal. Calcd (%) for C19H16N4S: C, 68.65%; H, 4.85%; N, 16.85%; S, 9.65%. Found: C, 69.32%; H, 4.77%; N, 17.10% ;S,9.97%.IR(KBr,cm-1)3299s, 3051vs,1533s,1439s,1304s,1203s,1174s,1106s,791s,756s,696s,655s,499s. MSI-MS:m / z=333.11for [M+H]+;

...

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Abstract

The invention discloses a thiosemicarbazone platinum complex taking 2-benzoyl pyridine as a ligand as well as a synthesis method and application of the thiosemicarbazone platinum complex. 2-benzoyl pyridine and thiosemicarbazone are selected for condensation reaction to obtain the ligand; and the ligand reacts with Pt (DMSO) 2Cl2 to obtain five new platinum complexes. In-vitro proliferation inhibition activity experiments are further carried out on the synthesized platinum complexes, and results show that the synthesized series of platinum complexes have generally good in-vitro activity, particularly have high specificity on human T24 and HeLa and HUVECs cells, and have little toxic effect on human normal cells. Chicken embryo chorion vascular experiments prove that the platinum complex has a good effect of inhibiting angiogenesis, and can inhibit the generation of tumor cell blood vessels by adjusting substance metabolism, blocking the combination of endothelial cell membrane receptors and angiogenesis factors, inhibiting endothelial cell migration and other mechanisms. The platinum complex is suitable for preparing high-efficiency and low-toxicity anti-tumor angiogenesis inhibition drugs.

Description

technical field [0001] The invention relates to a platinum complex, in particular to a platinum complex with 2-benzoylpyridine thiosemicarbazone as a ligand, a synthesis method and application thereof. Background technique [0002] According to the statistics of the World Health Organization, malignant tumors have become the second leading cause of human death, seriously threatening human health and life. Platinum antineoplastic drugs are the main anticancer drugs in clinical practice. However, platinum-based metal drugs have serious adverse reactions clinically, such as nephrotoxicity, bone marrow toxicity, ototoxicity, peripheral neurotoxicity, emetic effect and drug resistance. Therefore, the research and development of highly efficient and low-toxic antitumor drugs is a hot spot in current research. [0003] Condensation of thiosemicarbazides with ketones or aldehydes can obtain thiosemicarbazones, and thiosemicarbazones and their metal complexes have high antitumor ac...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCA61P35/00C07F15/0093
Inventor 杨峰王晓军楚永梁宏
Owner GUANGXI NORMAL UNIV
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