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6,7-dichloroquinoline-5,8-dione derivative transition metal complex and its synthesis method and application

A compound and composition technology, applied in the field of medicine, can solve problems such as limitations and inactivity

Active Publication Date: 2021-09-14
GUILIN NORMAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, cisplatin-based metal drugs have obvious side effects such as nephrotoxicity, bone marrow toxicity, ototoxicity, peripheral neurotoxicity, vomiting, and drug resistance caused by long-term use, and platinum-based antineoplastic drugs are not active against certain tumors. Insufficiency limits the application of these platinum drugs to some extent (Metzler-Nolte, N.; et al. Chem. Eur. J., 2016, 22, 12487-12494.)
At present, there is no 6,7-dichloroquinoline-5,8-dione (DQ) or 6,7-dichloro-2-methyl-quinoline-5,8-dione (DMQ) as the active ligand. Related reports on the method and application of transition metal complexes such as zinc, cobalt, nickel, copper, manganese and so on

Method used

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  • 6,7-dichloroquinoline-5,8-dione derivative transition metal complex and its synthesis method and application
  • 6,7-dichloroquinoline-5,8-dione derivative transition metal complex and its synthesis method and application
  • 6,7-dichloroquinoline-5,8-dione derivative transition metal complex and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: [Zn(DQ) 2 (CH 3 Oh) 2 ] (complex 1) synthesis

[0029] Weigh 2.0mmol of DQ and 1.0mmol of Zn(NO 3 ) 2 ·6H 2 O, placed in a 100.0mL high-temperature pressure-resistant tube, dissolved in 35.0mL of mixed solvent (V 甲醇 :V 二氯甲烷 =7:93), react at 65°C for 6.0h, filter the reactant, and volatilize the obtained filtrate at room temperature until its volume is 1 / 3 of the volume of the mixed solvent, a large number of reddish-brown blocky crystals are precipitated, collect the crystals , washed with methanol, and dried at 45°C to obtain the reddish-brown target complex 1. The yield was 90.0%.

[0030] The product obtained in this embodiment is characterized:

[0031] (1) X-ray single crystal diffraction:

[0032] Take a moderately sized reddish-brown bulk crystal and place it on Agilent’s SuperNova single crystal diffractometer, using graphite monochromatized Mo-K α ray for single crystal testing. The initial crystal structures of the products obtained...

Embodiment 2

[0052] Embodiment 2: [Zn(DMQ) 2 (CH 3 Oh) 2 ] (complex 2) synthesis

[0053] Weigh 2.0mmol of DMQ and 1.0mmol of Zn(NO 3 ) 2 ·6H 2 O, placed in a 100.0mL high-temperature pressure-resistant tube, dissolved in 5.0mL of mixed solvent (V 甲醇 :V 二氯甲烷 =99:1), react at 65°C for 3.0h, filter the reactant, and volatilize the obtained filtrate at room temperature until its volume is 1 / 3 of the volume of the mixed solvent, a large number of reddish-brown block crystals are precipitated, collected The crystals were washed with methanol and dried at 45°C to obtain the reddish-brown target complex 2. The yield was 65.3%.

[0054] The product obtained in this embodiment is characterized:

[0055] (1) X-ray single crystal diffraction:

[0056] Take a moderately sized reddish-brown bulk crystal and place it on Agilent’s SuperNova single crystal diffractometer, using graphite monochromatized Mo-K α ray for single crystal testing. The initial crystal structures of the products obta...

Embodiment 3

[0076] Embodiment 3: [Co(DQ) 2 (CH 3 Oh) 2 ] (complex 3) synthesis

[0077] Weigh 2.0mmol of DQ and 1.0mmol of Co(NO 3 ) 2 ·6H 2 O, placed in a 100.0mL high-temperature pressure-resistant tube, dissolved in 80.0mL of mixed solvent (V 甲醇 :V 二氯甲烷 =23:77) in the mixed solution of methanol and dichloromethane (v:v=23:77), react at 120°C for 72.0h, filter the reactant, and volatilize the obtained filtrate at room temperature until its volume is equal to that of the mixed solvent. When the volume was 1 / 3, a large number of reddish-brown blocky crystals were precipitated. The crystals were collected, washed with methanol, and dried at 45°C to obtain the reddish-brown target complex 3. The yield was 92.8%.

[0078] The product obtained in this embodiment is characterized:

[0079] (1) X-ray single crystal diffraction:

[0080] Take a moderately sized reddish-brown bulk crystal and place it on Agilent’s SuperNova single crystal diffractometer, using graphite monochromatized M...

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Abstract

The invention discloses a class of 6,7-dichloroquinoline-5,8-dione derivative transition metal complexes and a synthesis method and application thereof. The complex of the present invention has the structure shown in the following formula (I), and its synthesis method is to put metal nitrate and the compound shown in the following formula (II) in a mixed solvent, and carry out coordination under heating or without heating reaction, the reactant is cooled, allowed to stand, volatilized, and crystals are precipitated to obtain the target compound; wherein, the mixed solvent is a composition of methanol or ethanol and dichloromethane; the complex of the present invention is effective for certain tumor cells The strain has significant inhibitory activity and has low toxicity to normal human liver cells. The compounds shown in the formula (I) and the formula (II) are respectively as follows: wherein, M represents a divalent metal element selected from the fourth period of the periodic table; R represents H or CH 3 , X means H 2 O, CH 3 OH or CH 3 CH 2 Oh.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 6,7-dichloroquinoline-5,8-dione derivative transition metal complex and a synthesis method and application thereof. Background technique [0002] Since Rosenberg discovered that cisplatin (cisplatin) has anticancer activity in 1969, the research and development of metal antitumor drugs has aroused widespread interest (Sadler, P.J.; et al. Chem. Commun., 2015, 51, 9169-9172 .). However, cisplatin-based metal drugs have obvious side effects such as nephrotoxicity, bone marrow toxicity, ototoxicity, peripheral neurotoxicity, vomiting, and drug resistance caused by long-term use, and platinum-based antineoplastic drugs are not active against certain tumors. Insufficiency limits the application of these platinum drugs to some extent (Metzler-Nolte, N.; et al. Chem. Eur. J., 2016, 22, 12487-12494.). In order to overcome the defects of platinum-based drugs, in addition to further r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/06C07F15/06C07F15/04C07F1/08C07F13/00A61K31/315A61K31/30A61K31/282A61K31/28A61K31/295A61P35/00
CPCA61P35/00C07F1/08C07F3/06C07F13/005C07F15/045C07F15/065
Inventor 邹碧群何瑞杰唐洁方毅林莫绪
Owner GUILIN NORMAL COLLEGE
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