Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method and antitumor activity of ruthenium complexes containing benzothiazole

A technology of benzothiazole and ruthenium complexes, applied in the field of new ruthenium complexes, can solve the problems of large toxic and side effects, drug resistance of cancer cells, low water solubility, etc.

Inactive Publication Date: 2014-07-02
JIANGNAN UNIV
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main clinical treatment method for cancer is chemotherapy, but the current chemotherapeutic agents are cisplatin and other drugs, which have serious side effects and drug resistance of cancer cells, and the water solubility of anticancer drugs such as cisplatin is small

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method and antitumor activity of ruthenium complexes containing benzothiazole
  • Preparation method and antitumor activity of ruthenium complexes containing benzothiazole
  • Preparation method and antitumor activity of ruthenium complexes containing benzothiazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation of bipyridin[3,2-a:2',3'-c]phenazine-10-acid

[0029] Add 2.1 g (10 mmol) of 1,10-phenanthroline-5,6-dione (10 mmol) and 100 mL of ethanol into a 250 mL three-neck flask, and remove the air. Add 1.52g (10mmol) 2,3-diaminobenzoic acid under the protection of nitrogen, reflux at 80°C, stir the reaction, TLC thin layer chromatography to track the reaction progress, the reaction is completed after about 5h, after the reaction is stopped, cool, suction filter, and use After washing with dichloromethane and ethanol, 2.88 was obtained as a light yellow solid with a yield of 88.3%.

Embodiment 2

[0030] Example 2: Preparation of 2-(10-dipyridyl[3,2-a:2′,3′-c]phenazine)benzothiazole

[0031]In a 100mL three-necked flask, add 0.303g (0.929mmol) bipyridyl[3,2-a:2′,3′-c]phenazine-10-acid and an appropriate amount of polyphosphoric acid, nitrogen protection, and then pipette Pipette 1mL (0.929mmol) o-aminothiophenol, heat to 140°C with an oil bath, stir with a stirrer on, react for 20h, cool and pour into 100g of crushed ice, filter with suction, add 200mL of water to the filtrate , and the pH was adjusted to neutral with ammonia water, and suction filtered again, and the resulting solid was washed with water and ethanol. After drying, 0.192 g of a yellow-green solid was obtained, with a yield of 51.2%.

Embodiment 3

[0032] Embodiment 3: preparation [Ru(bpy) 2 BFDPP]Cl 2 and [Ru(phen) 2 BFDPP]Cl 2 :

[0033] Add 0.20mmol cis-Ru(bpy) successively to a 100mL three-neck flask 2 Cl 2 2H 2 O or cis-Ru(bpy) 2 Cl 2 2H 2 O and 0.2g (0.5mmol) 2-(10-dipyridyl[3,2-a:2′,3′-c]phenazine)benzothiazole, add 24mL ethanol, immerse the 6mL water glass tube into the liquid and blow with nitrogen gas Soak 20mIn to remove the dissolved oxygen in the solvent. The temperature was raised to 80°C, and the reaction was kept under reflux for 24 hours, and the reaction was stopped to obtain a red solution. The reaction solution was poured into 30mL deionized water and stirred for 5mIn. Suction filtration, discard the insoluble matter. The solvent in the filtrate was distilled off under reduced pressure, and the obtained solid was vacuum-dried. The dried solid was separated by column chromatography (neutral alumina column 200-300 mesh, eluent: acetonitrile / toluene=1 / 1). After the separation, the solvent w...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses ruthenium polypyridine complexes, a preparation method thereof and application of the ruthenium polypyridine complexes as anti-cancer drugs. The ruthenium polypyridine complexes are ruthenium (II) complexes with 2-(10-dipyridine[3,2-a:2',3'-c]phenazine)benzothiazole as a main ligand (BFDPP) and bipyridine (pby) and phenanthroline (phen) as auxiliary ligands. The molecular formulas of the ruthenium (II) complexes are [Ru(pby)2(BFDPP)]C12 and [Ru(phen)2(BFDPP)]C12, respectively, wherein BFDPP is 2-(10-dipyridine[3,2-a:2',3'-c]phenazine)benzothiazole. The preparation method comprises the following steps: reacting o-phenanthroline-5,6-dione with 2,3-diaminobenzoic acid in ethanol so as to prepare a yellow solid; reacting the yellow solid with 2-aminothiophenol in polyphosphoric acid so as to prepare the ligand BFDPP; and reacting the ligand BFDPP with Ru(pby)2C12.H2O or Ru(phen)2C12.H2O and subjecting an obtained solid to column chromatographic purification so as to obtain the ruthenium polypyridine complexes. The preparation method is simple and has mild reaction conditions; the ruthenium polypyridine complexes have good dissolvability in water; the structures of intermediate reaction products and the target products are stable. The complexes provided by the invention have good inhibitory effects on the skin cancer cell line A375 and the breast cancer cell MCF-7.

Description

technical field [0001] The present invention relates to a class of novel ruthenium complexes containing benzothiazole and dipyridyl[3,2-a:2',3'-c]phenazine, a preparation method thereof, and the antitumor activity of the ruthenium complexes . Background technique [0002] In my country, the cancer mortality rate ranks second among all diseases, and the number of cancer patients is increasing at a rate of 1.6-1.7 million per year. According to statistics from the Ministry of Health, the annual sales of anticancer drugs in 2010 exceeded 60 billion US dollars. The main clinical treatment method for cancer is chemotherapy, but the current chemotherapeutic agents are cisplatin and other drugs, which have serious side effects and drug resistance of cancer cells, and the water solubility of anticancer drugs such as cisplatin is small . Therefore, the research and development of new anticancer drugs with high efficiency, low toxicity and no cross-resistance has always been a rese...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07F15/00C07D471/14A61P35/00
Inventor 郑昌戈董文献童蓉蓉
Owner JIANGNAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com