1,1,1-triphenyl-N-(1-(pyridine-2-methylene) methylamine containing complex as well as preparation method and application thereof

A complex, triphenyl technology, applied in the field of chemical pharmacy, can solve the problems such as the anti-cancer activity needs to be improved, there is no semi-sandwich structure, etc., and achieve the effects of easy control of chemical components, low cost and high activity

Active Publication Date: 2018-07-06
QUFU NORMAL UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The anticancer activity of the complexes prepared in the prior art still needs to be improved, and there is no research on the self-luminescence of the half-sandwich structure in intracellular imaging

Method used

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  • 1,1,1-triphenyl-N-(1-(pyridine-2-methylene) methylamine containing complex as well as preparation method and application thereof
  • 1,1,1-triphenyl-N-(1-(pyridine-2-methylene) methylamine containing complex as well as preparation method and application thereof
  • 1,1,1-triphenyl-N-(1-(pyridine-2-methylene) methylamine containing complex as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 50.0mg iridium dimer (formula (I) R1 is 1.2.3.4.5-pentamethylcyclopentadienyl, R2 is hydrogen, M is metallic iridium), 46.3mg 1,1,1-triphenyl -N-(1-(pyridine-2-methylene)methanamine was placed in a 250mL Schlenk bottle, vacuumed, and nitrogen gas was injected three times, and 20mL of analytically pure ethanol was added with a needle, and stirred at room temperature for 24h. Add 60 mg KPF6, spin dry with rotary evaporator, then dissolve with CH2Cl2, filter with diatomaceous earth, and recrystallize by diffusion method to obtain red crystals. Yield: 52.48mg (61.3%).

[0045] Such as figure 1 As shown, the NMR characterization is: [(η5-Cp*)Ir(N^N)Cl]PF6 (1). 1H NMR (500 MHz, DMSO) δ 8.61 (d, J = 4.7 Hz, 1H), 8.33 ( d, J = 7.9 Hz, 1H), 7.98 (t, J = 7.0Hz, 1H), 7.77 (s, 1H), 7.51 (ddd, J = 7.5, 4.8, 1.1 Hz, 1H), 7.37 (t, J = 7.5Hz, 6H), 7.31 (t, J = 7.3 Hz, 3H), 7.24 – 7.21 (m, 6H), 1.75 (s, 15H). Anal.Calcd. For [(η5- Cp*)Ir(N ^N)Cl]PF6 (856.3): C, 49.09; H, 4.12; N, 3.2...

Embodiment 2

[0047] 50.0mg iridium dimer (formula (I) R1 is 4-(2.3.4.5-tetramethylcyclopentadiene)-1'1-biphenyl, R2 is hydrogen, M is metallic iridium), 43.6 mg 1,1,1-Triphenyl-N-(1-(pyridine-2-yl)ethylidene)methanamine was placed in a 250mL Schlenk bottle, vacuumed, three times with nitrogen, and added with a needle 20 mL of analytically pure ethanol, stirred at room temperature for 24 hours, added 60 mg KPF6, spin-dried with a rotary evaporator, dissolved in CH2Cl2, filtered with diatomaceous earth, and recrystallized by diffusion method to obtain red crystals, the single crystal structure of complex 2 Such as figure 2 shown. Yield: 40.05 mg (40.3%).

[0048] Such as image 3 As shown, the NMR characterization is: [(η5-Cpxbiph )Ir(N^N)Cl]PF6 (2). Yield: 40.05mg, 40.3%.1H NMR (500 MHz, DMSO) δ 13.59 (d, J = 9.6 Hz, 2H), 9.54 (d, J =9.7 Hz, 3H), 8.80 (d, J = 5.4 Hz, 2H), 8.57 – 8.13 (m, 5H), 8.05 – 7.65 (m,8H), 7.64 – 7.23 (m, 8H), 1.83 (dd, J = 33.5, 10.8 Hz, 12H). Anal. Calcd. For[...

Embodiment 3

[0050] 50.0mg ruthenium dimer (formula (III) R1 is phenyl, R2 is hydrogen, M is metal ruthenium), 63.1mg 1,1,1-triphenyl-N-(1-(pyridine-2-yl )Ethylene)methylamine was placed in a 250mL Schlenk bottle, vacuumed, and nitrogen gas was injected three times, 20mL of analytically pure ethanol was added with a needle, stirred at room temperature for 24 hours, 60 mg of KPF6 was added, and spun with a rotary evaporator After drying, dissolve with CH2Cl2, filter with diatomaceous earth, and recrystallize by diffusion method to obtain red crystals. The single crystal structure of complex 3 is as follows: Figure 4 shown. Yield: 45.43 mg (61.3%).

[0051] Such as Figure 5 As shown, the NMR characterization is: [(η6-bz )Ru(N^N)Cl]PF6 (3). 1H NMR (500 MHz, DMSO) δ 9.63 (d, J = 5.3 Hz, 1H), 8.78 (s , 1H), 8.32 (d, J = 7.9 Hz, 1H), 8.26 (t, J = 8.2 Hz, 1H), 7.89 – 7.86 (m, 1H), 7.45 (ddd, J = 27.3, 19.4, 7.3Hz, 15H), 5.61 (s, 6H). Anal. Calcd. For [(η6- bz )Ir(N^N)Cl]PF6 (708.04): C,52.5...

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Abstract

The invention particularly discloses a 1,1,1-triphenyl-N-(1-(pyridine-2-methylene) methylamine containing complex and belongs to the field of chemical pharmacy. A molecular structural formula of the complex is described in the description. By adopting the complex prepared by a preparation method, the whole complex can be endowed with high anticancer activity, mitochondria targeting and nucleus targeting, has selectivity to cancer cells and has important significance of studying the drug targeting. By taking N'N as an anion ligand of bidentate chelating, the novel complex with high anticancer activity is synthesized and is good in effect and high in activity in cancer prevention and cell imaging. The 1,1,1-triphenyl-N-(1-(pyridine-2-methylene) methylamine containing complex has the advantages of simpleness in technology, low cost, easiness in controlling chemical components, good repeatability, high yield and the like.

Description

technical field [0001] The invention relates to a metal complex, specifically a complex containing 1,1,1-triphenyl-N-(1-(pyridine-2-methylene)methanamine, its preparation method and application, belonging to chemical pharmaceuticals field. Background technique [0002] In 1965, the synthesis of cisplatin revolutionized the treatment of cancer by radiotherapy alone, and many cisplatin derivatives derived from it have also been biologically evaluated. With people's continuous and in-depth research, three platinum anticancer drugs, cisplatin, carboplatin and oxaliplatin, have become metal anticancer drugs approved worldwide, and they are the only metal-based anticancer drugs used in clinical practice worldwide. anticancer drugs. Metal complexes are used in the treatment of about 50% of all tumors, but their use is often accompanied by toxic side effects, such as nephrotoxicity and drug dependence. is glutathione) is inactivated and will flow out of the cell. In order to ove...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00G01N21/63
CPCC07F15/0033C07F15/0046G01N21/63
Inventor 刘哲李娟娟郭丽华葛兴兴张均铭
Owner QUFU NORMAL UNIV
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