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Chiral binuclear Ir (III) metal-organic double helix structure compound and preparation method thereof

A double helix structure and compound technology, applied in the direction of indium organic compounds, organic chemical methods, platinum group organic compounds, etc., can solve the problems of difficult to maintain chiral structure and low chemical stability, and achieve good biocompatibility, phosphorescence The effect of long emission life and strong binding effect

Active Publication Date: 2022-05-20
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The metal ions and organic ligands in the chiral helical structure obtained by this method are often connected by coordination bonds, the chemical stability is not high, and various isomers will be produced during the assembly process, and the chiral structure is difficult to maintain.

Method used

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  • Chiral binuclear Ir (III) metal-organic double helix structure compound and preparation method thereof
  • Chiral binuclear Ir (III) metal-organic double helix structure compound and preparation method thereof
  • Chiral binuclear Ir (III) metal-organic double helix structure compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] 1) Take the ligand 4-(2-pyridyl)-benzaldehyde (916 mg, 5 mmol), IrCl 3 • xH 2 O (600 mg, 2 mmol) was placed in a 50 mL two-necked flask, 30 mL of mixed solvent ethylene glycol methyl ether / water (3 / 1, V / V) was added, and argon was introduced for 30 minutes to exhaust the air in the system Afterwards, the temperature was raised to 120 °C and stirred for 24 h in the dark. After cooling to room temperature, the filter cake was obtained by suction filtration, and the filter cake was washed with water, ethanol and ether respectively to obtain the red dichloro-bridged complex [Ir(L-CHO) 2 Cl] 2 .

[0048] 2) Weigh [Ir(L-CHO) 2 Cl] 2 (300 mg, 0.25 mmol) into a 250 mL three-necked flask, dissolved in 100 mL of dry dichloromethane / methanol (4 / 1, V / V) mixed solvent, then added sodium methoxide (40.50 mg, 0.75 mmol), and ventilated After 30 minutes, exhaust the air in the system and add L-proline (L-Pro) (86.40 mg, 0.75 mmol), heat up to 50 °C and reflux, and react in the da...

Embodiment 2

[0051] Take L1-a (156.80 mg, 0.20 mmol) and dissolve it in 120 mL of dry dichloromethane solution, blow in argon, exhaust the air in the system, add the ligand dipyrido[3,2-a:2',3' -c]phenazine (dppz, 84.70 mg, 0.30mmol), after stirring at room temperature in the dark for 10 h, the solvent was removed by rotary evaporation under reduced pressure, and separated by silica gel column chromatography to obtain a yellow solid L1-b. The nuclear magnetic spectrum of the obtained compound L1-b is as figure 2 shown.

Embodiment 3

[0053] 1) Weigh the intermediate product [Ir(L-CHO) of Example 1 2 Cl] 2 (300.0 mg, 0.25 mmol) into a 250 mL three-necked flask, dissolved in 100 mL of dry dichloromethane / methanol (4 / 1, V / V) mixed solvent, then added sodium methoxide (40.5 mg, 0.75 mmol), and ventilated After 30 min, exhaust the air in the system, add D-proline (D-Pro) (86.4 mg, 0.75 mmol), heat up to 50 °C and reflux, and react in the dark for 12 h, cool to room temperature, and then add water, dichloro Extracted with methane and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated to remove solvent, separated by silica gel column chromatography to obtain red solid Ir(L-CHO) 2 (D-Pro).

[0054] 2) Take Ir(L-CHO) 2 (D-Pro) (40.40 mg, 0.06 mmol) was dissolved in 30 mL of dry acetonitrile solution, argon gas was introduced to exhaust the air in the system, trifluoroacetic acid (9 μL, 0.12 mmol) was slowly added, and stirred at room temperature in the dark After 4 h, ammonium hexafluo...

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Abstract

The invention discloses a chiral binuclear Ir (III) metal-organic double helix structure compound and a preparation method thereof, and belongs to the technical field of medicine synthesis. According to the chiral binuclear Ir (III) metal-organic double helix structure compound, chiral Ir (III)-based complexes L1 and L2 are used as construction modules and are subjected to imine condensation with chiral cyclohexanediamine to obtain chiral metal-organic helix structures L1-i-D1 and L2-i-D2, the preparation method is simple, and the yield is high. The binuclear Ir (III) chiral metal-organic double helix structure compound prepared by the invention has good photophysical properties and biocompatibility, can generate a relatively strong binding effect with DNA, and has a good clinical application prospect.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a chiral dinuclear Ir(III) metal-organic double helix structure compound and a preparation method thereof. Background technique [0002] Photodynamic therapy (Photodynamic Therapy, PDT) is an emerging cancer treatment method in recent decades. It has the advantages of non-invasive treatment, low toxicity and side effects, good spatiotemporal selectivity, and strong applicability. Now photodynamic therapy has been applied in the treatment of lung cancer, bladder cancer and esophageal cancer. Researchers believe that photodynamic therapy is a milestone in the history of cancer treatment. Photodynamic therapy requires three necessary conditions: photosensitizer, oxygen and light. Photosensitizer, as the core factor, has received extensive attention from scientists in recent years. Transition metal Ir(III) complexes are star molecules in the field of PDT cancer therapy beca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06A61K41/00A61P35/00
CPCC07F15/0033C09K11/06A61K41/0057A61P35/00C09K2211/185C07B2200/07
Inventor 何成郝晓柔李学召
Owner DALIAN UNIV OF TECH
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