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Cyclometalated ruthenium complex as well as synthetic method and application thereof

A technology of ruthenium complexes and cyclometallation, which is applied in the synthesis of cyclometallated ruthenium complexes, and in the field of cyclometallated ruthenium complexes, can solve problems such as drug failure, cumulative drug resistance of tumor cells, and reduced tumor cell killing effect

Active Publication Date: 2017-06-13
GUANGDONG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the deepening of the research, researchers found that the use of platinum-based anticancer drugs will lead to the gradual accumulation of drug resistance in tumor cells, resulting in a decrease in the killing effect of the drug on tumor cells, thus making the drug gradually ineffective

Method used

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  • Cyclometalated ruthenium complex as well as synthetic method and application thereof
  • Cyclometalated ruthenium complex as well as synthetic method and application thereof
  • Cyclometalated ruthenium complex as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Synthesis of Cyclometallated Ruthenium Complexes Ru1

[0100] ①Synthesis of N-Ts-β-phenylethylamine

[0101] Dissolve phenethylamine (12.1g, 100mmol) and triethylamine (30.3g, 300mmol) in 85ml of dichloromethane, then slowly add p-toluenesulfonyl chloride (18.05g, 95mmol) at -15°C, drop After the addition, remove the freezer, return to room temperature (25°C), stir for 6 hours, TLC detects that the raw material point disappears (phenethylamine), indicating that the reaction is complete; then, add 100ml of water to wash, and wash with 25ml of 1M HCl solution until the solution is weakly acidic , and the solvent was spin-dried to obtain an oil, which was dissolved by adding 10ml of ethanol and dissolved in a hot water bath at 70°C; then adding 50ml of water, stirring, and a white precipitate was precipitated, put it in a refrigerator at 4°C, and filtered with suction to obtain N-Ts-β-phenethylamine, the yield is 90%.

[0102] ②Synthesis of 1-phenyl-2-tosyl-1,2,3,4-tetra...

Embodiment 2

[0111] Synthesis of Cyclometallated Ruthenium Complexes Ru2

[0112] ①Synthesis of N-Ts-β-phenylethylamine

[0113] Dissolve phenethylamine (12.1g, 100mmol) and triethylamine (30.3g, 300mmol) in 80ml of dichloromethane, then slowly add p-toluenesulfonyl chloride (18.05g, 95mmol) at -10°C, drop After the addition, remove the freezer, return to room temperature (25°C), stir for 5 hours, TLC detects that the raw material point disappears (phenethylamine), indicating that the reaction is complete; then, add 100ml of water to wash, and wash with 25ml of 1M HCl solution until the solution is weakly acidic , and the solvent was spin-dried to obtain an oil, which was dissolved by adding 10ml of ethanol and dissolved in a hot water bath at 70°C; then adding 50ml of water, stirring, and a white precipitate was precipitated, put it in a refrigerator at 4°C, and filtered with suction to obtain N-Ts-β-phenethylamine, the yield is 88%.

[0114] ② 1-p-tolyl-2-tosyl-1,2,3,4-tetrahydroisoqui...

Embodiment 3

[0123] Synthesis of Cyclometallated Ruthenium Complexes Ru3

[0124] ①Synthesis of N-Ts-β-phenylethylamine

[0125] Dissolve phenethylamine (12.1g, 100mmol) and triethylamine (30.3g, 300mmol) in 80ml of dichloromethane, then slowly add p-toluenesulfonyl chloride (18.05g, 95mmol) at -8°C, drop After the addition, remove the freezer, return to room temperature (25°C), stir for 4 hours, TLC detects that the raw material point disappears (phenethylamine), indicating that the reaction is complete; then, add 120ml of water to wash, and wash with 25ml of 1M HCl solution until the solution is weakly acidic , and the solvent was spin-dried to obtain an oil, which was dissolved by adding 12ml of ethanol and dissolved in a hot water bath at 70°C; then adding 50ml of water, stirring, and a white precipitate was precipitated, put it in a refrigerator at 3°C, and filtered with suction to obtain N-Ts-β-phenylethylamine, the yield is 92%.

[0126] ②Synthesis of 1-phenyl-2-tosyl-1,2,3,4-tetr...

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Abstract

The invention provides a cyclometalated ruthenium complex as well as a synthetic method and application thereof. The cyclometalated ruthenium complex has a chemical general formula of [Ru(L)2(PhIQ-R)](PF6), wherein PhIQ-R serves as a main ligand; when R is equal to H, PhIQ-R refers to 1-phrnyl-isoquinoline; when R is equal to Me, PhIQ-R refers to 1-p-methylphenyl-isoquinoline; and L is an auxiliary ligand and is preferably selected from 2,2-dipyridyl or phenanthroline. The cyclometalated ruthenium complex [Ru(L)2(PhIQ-R)](PF6) has more excellent antitumor activity than cis-platinum and is easily synthesized; and the cyclometalated ruthenium complex disclosed by the invention has excellent antitumor activity and the advantages of transmembrane simplicity, high targeting property and low toxicity, is applied to preparing various anti-cancer drugs or DNA insertion agents and has excellent clinical application prospects.

Description

technical field [0001] The invention belongs to the field of antitumor drugs, and in particular relates to a cyclometalated ruthenium complex, and also relates to a synthesis method and application of the cyclometallated ruthenium complex. Background technique [0002] Cancer is a common disease that directly threatens human life in today's world. Finding new anti-tumor drugs with high efficiency and low toxicity that can act on specific targets has always been the goal of human unremitting efforts. [0003] For example, cisplatin is the first-line drug for the treatment of various solid tumors, combined with VP-16 (EP regimen) is the first-line regimen for the treatment of SCLC or NSCLC, and combined with MMC, IFO (IMP regimen), or NVB is the common regimen for the treatment of NSCLC. Combination chemotherapy based on DDP is also the main treatment plan for advanced ovarian cancer, osteosarcoma and neuroblastoma. It is effective for multi-site squamous cell carcinoma and tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/0046
Inventor 陈锦灿陈兰美李宝军张瑶
Owner GUANGDONG MEDICAL UNIV