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Ruthenium complex as well as preparation method and application thereof

A technology of ruthenium complexes and aromatic rings is applied in the field of ruthenium pyridine complexes with substituents and their preparation, which can solve the problems of myelosuppression drug resistance, toxicity and the like, and achieve the effects of increasing reaction temperature, low toxicity and speeding up reaction speed.

Inactive Publication Date: 2014-03-26
MACAU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition to killing cancer cells, commonly used clinical anticancer drugs are highly toxic to normal cells, accompanied by serious side effects such as bone marrow suppression and drug resistance

Method used

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  • Ruthenium complex as well as preparation method and application thereof
  • Ruthenium complex as well as preparation method and application thereof
  • Ruthenium complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 [H(3-BrPy)][trans-RuCl 4 (DMSO)(3-BrPy)] Preparation (Compound 1, L=3-BrPy, 3-Bromopyridine)

[0055] Weigh the starting material trans-[RuCl 4 (DMSO) 2 ][(DMSO) 2 H] 0.10g (0.18mmol) was ground into a fine powder, dissolved in 8ml of acetone, and 0.07ml (0.72mmol) of 3-bromopyridine was added. The reaction was carried out ultrasonically for 3 hours, the orange powder produced was filtered and washed with acetone and ether, and the silica gel was dried overnight. Obtained orange powder: 0.10 g. Yield: 87%.

[0056] The physical and chemical properties of the obtained complex (compound 1) are described as follows: Morphology: orange needle-like crystallites. Molecular weight: 638.01. Melting point: 181-183°C. Molecular formula: C 12 H 15 Cl 4 Br 2 N 2 ORuS. Elemental analysis calculated value: C 22.59, H 2.37, N 4.39%; elemental analysis determined value: C 22.93, H 2.29, N 4.42%. UV / Vis(25℃,H 2 O)λmax, nm(ε,L·mol -1 ·Cm -1 ): 293(3280), 396(3980), 462(480). ...

Embodiment 2

[0057] Example 2 [H(4-BrPy)][trans-RuCl 4 (DMSO)(4-BrPy)] Preparation (Compound 2, L=4-BrPy, 4-Bromopyridine)

[0058] 4-Bromopyridine is unstable and must be converted to 4-bromopyridine after treatment with 4-bromopyridine hydrochloride.

[0059] Transformation process: Dissolve 1 g of 4-bromopyridine hydrochloride in 5 ml of water. Use 0.5mol·L -1 Adjust the pH value of NaOH solution to make it greater than 6. Extract with 3ml of chloroform and take out the chloroform layer (lower layer). Then repeat the extraction with 3ml chloroform respectively, combine the three extracts, and use anhydrous Na 2 SO 4 Dehydrate and reserve (store in refrigerator).

[0060] Weigh the starting material trans-[RuCl 4 (DMSO) 2 ][(DMSO) 2 H] 0.11g (0.20mmol), dissolved in 8ml of acetone, and 2ml of the above stock solution was added. After 3 hours of ultrasonic reaction, an orange solid powder was finally generated. Filter and wash with acetone and ether. The silica gel was dried overnight. Obt...

Embodiment 3

[0062] Example 3 [H(3-ClPy)][trans-RuCl 4 (DMSO)(3-ClPy)] Preparation (Compound 3, L=3-ClPy, 3-chloropyridine)

[0063] The preparation method is the same as in Example 1. Yield: 71.37%.

[0064] The physical and chemical properties are described as follows: Morphology: orange-yellow crystallites; molecular formula: C 12 H 15 Cl 6 N 2 ORuS; molecular weight: 549.11; elemental analysis calculated value: C 26.25, H 2.75, N 5.10%; measured value: C 26.25, H 2.87, N 4.71%. UV / Vis(25℃,H 2 O)λmax, nm(ε,L·mol -1 ·Cm -1 ): 290(3480), 396(4000), 462(490). Infrared spectrum characteristic peak (cm -1 ): 3089, 3050, 2916, 1516 (vs), 1465, 1452, 1421, 1073, 1022, 430 (s). 1 H-NMR spectrum (DMSO-d 6 ) δ: 8.76ppm, 8.62ppm, 8.11ppm, 7.60ppm, -1.96ppm, -12.85ppm.

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Abstract

The invention discloses a ruthenium complex containing a pyridine derivative as well as a preparation method and an application of the ruthenium complex. The structural formula of the complex is shown in the formula (I). The preparation method comprises the steps: grinding a reaction initiator trans-[RuCl4(SOR1R2)2][(SOR1R2)2H] into fine powder; stirring the initiator and ligand or performing ultrasonic oscillation in a reaction solvent, wherein the molar rate of the initiator to the ligand is 1:2-1:8 and the reaction temperature is 25-80 DEG C; or carrying out backflow; filtering precipitate formed after ultrasonic oscillation, and washing with acetone and diethyl ether; and drying by a silicon rubber dryer and keeping overnight. According to the preparation method of the ruthenium complex, the reaction time is short and the yield is high; and by using the prepared NA MI-A derivate, the anti-metastasis pesticide effect of Lewis experimental lung-cancer mice is significant, and the toxicity is low.

Description

Technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a pyridine ruthenium complex with a substituent and a preparation method and application thereof. Background technique [0002] Lung cancer is a malignant tumor with the highest morbidity and mortality in men and the second highest mortality in women (the highest morbidity is breast cancer). With hundreds of thousands of deaths every year, it is the most harmful cancer to our health. Moreover, the early symptoms of lung cancer are not obvious, and most of the lung cancer patients found are advanced and metastatic. At present, there is no effective drug treatment except for early surgical resection. Mostly comfort treatment. Tumor patients die mainly from tumor metastasis and the toxicity of antitumor drugs. In addition to killing cancer cells, anti-cancer drugs commonly used in clinical practice are more toxic to normal cells and have serious side effects such as bone...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00A61P35/04A61P35/02
Inventor 梁国刚梁曜华毕葳
Owner MACAU UNIV OF SCI & TECH
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