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3-benzimidazole-6, 7-piperonylcyclo-2(1H)-quinolinone-zinc complex and preparation method and application thereof

A compound and reaction technology, applied in the field of medicine, can solve the problems of drug resistance, no 3-benzimidazole, and large toxic and side effects, and achieve the effects of stable quality, short preparation cycle and high yield

Active Publication Date: 2018-12-18
德州市洛泰商贸有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] As commonly used anticancer drugs in clinical practice, platinum-based metal-based anticancer drugs (such as cisplatin, carboplatin, oxaliplatin, etc.) susceptibility to drug resistance
At present, there are no related reports on the preparation method and application of 3-benzimidazole-6,7-pipercycline-2(1H)-quinolinone-zinc complex

Method used

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  • 3-benzimidazole-6, 7-piperonylcyclo-2(1H)-quinolinone-zinc complex and preparation method and application thereof
  • 3-benzimidazole-6, 7-piperonylcyclo-2(1H)-quinolinone-zinc complex and preparation method and application thereof
  • 3-benzimidazole-6, 7-piperonylcyclo-2(1H)-quinolinone-zinc complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Put 3.05g of compound (10mmol) shown in formula (II) and 1.40g of zinc chloride (11mmol), 10mL of methylene chloride and 10mL of methanol into the autoclave, then add 1mL of triethylamine, stir well (at this time the system pH = 7.0), the temperature was raised to 90°C for 14 hours. After the reaction, it was cooled, and yellow-green crystals were precipitated. The crystals were collected and dried to obtain 2.69 g of yellow-green crystals, with a yield of 60.50%.

[0025] The product obtained in this implementation is characterized by infrared, proton nuclear magnetic resonance spectrum, carbon spectrum, mass spectrum and X-single crystal diffraction, as follows:

[0026] (1) IR(KBr): 3432(m, NH), 2967, 2923(w, Ar-H), 2335(w, C=C), 1645(m, C=O), 1632(m, Ar- H),1048,1037(m,C-O-C)cm –1 ;

[0027] (2) 1 H NMR (500MHz, DMSO-d 6 )δ: 12.90(s,brd,1H,NH),12.65(s,brd,1H,NH),8.97(s,1H,H-Ar),7.72(s,2H,H-Ar),7.44(s ,1H,H-Ar),7.25(s,2H,H-Ar),6.88(s,1H,H-Ar),6.18(s,2H,OCH 2 O)...

Embodiment 2

[0038] Take 3-benzimidazole-6,7-pipercycline-2(1H)-quinolinone (305mg, 1mmol), 140mg of zinc chloride (1.1mmol), 8mL of dichloromethane and 8mL of methanol into an autoclave , then added 0.1 mL of triethylamine, stirred evenly (pH of the system at this time = 5.8), raised the temperature to 85° C. and reacted for 16 h, and obtained 200 mg of yellow-green crystals after cooling. Yield 45.00%.

[0039] The product obtained in this example was analyzed by infrared, hydrogen nuclear magnetic resonance, carbon spectrum, mass spectrum and X-single crystal diffraction, and it was determined that the product obtained in this example was the target compound.

Embodiment 3

[0040] Example 3: Preparation of 3-benzimidazole-6,7-piperone-2(1H)-quinolinone-zinc complex

[0041] Take 3-benzimidazole-6,7-pipercycline-2(1H)-quinolinone (610mg, 2mmol), 285mg of zinc chloride (1.2mmol), 10mL of dichloromethane and 5mL of ethanol into an autoclave , then add 5 drops of triethylamine (you can’t use ammonia water, other products will be obtained), stir evenly (the pH of the system at this time=5.0), heat up to 65°C and react for 16h, and after cooling, 492.25 mg of yellow-green crystals are obtained. Yield 55.00%.

[0042] The product obtained in this example was analyzed by infrared, hydrogen nuclear magnetic resonance, carbon spectrum, mass spectrum and X-single crystal diffraction, and it was determined that the product obtained in this example was the target compound.

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Abstract

The invention discloses a 3-benzimidazole-6, 7-piperonylcyclo-2(1H)-quinolinone-zinc complex and a preparation method and application thereof. The preparation method of the complex mainly comprises: putting a compound shown in the formulas (II) and zinc chloride into an organic solvent, adjusting pH of the system to 5-7 and performing a coordination reaction process under heating or no heating toobtain a desired product. Compared with the common antitumor drug cisplatin, the complex has higher inhibitory activity to human liver cancer cells Hep G2 and lower toxicity to normal cells and is expected to be used for preparation of antitumor drugs. The structure of the complex is shown in the formula (I). The raw material for preparation of the complex is shown in the formulas (II).

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a 3-benzimidazole-6,7-piperone-2(1H)-quinolinone-zinc complex and a preparation method and application thereof. Background technique [0002] As commonly used anticancer drugs in clinical practice, platinum-based metal-based anticancer drugs (such as cisplatin, carboplatin, oxaliplatin, etc.) susceptible to drug resistance. In order to solve or improve the problems of high toxicity and side effects of platinum-based metal-based anticancer drugs, scientists have proposed effective solutions [T.W.Hambley, Chemistry.Metal-based therapeutics [J]. Science, 2007, 318 (5855): 1392-1393; K.H.Thompson, C.Orvig, Boon and Bane of Metal Ions in Medicine[J].Science,2003,300(5621):936-939.]: Research and development of non-platinum metal anti-tumor drugs, expanding metal compounds type and scope. [0003] Zinc is an essential trace element for the human body. It plays an important regulat...

Claims

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Application Information

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IPC IPC(8): C07F3/06A61P35/00A61K31/4741
CPCA61P35/00C07F3/003
Inventor 张业李芳耀段小群徐勤
Owner 德州市洛泰商贸有限公司
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