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3-benzimidazole-2(1H)-quinolinone derivative and preparation method and application thereof

A reaction and compound technology, applied in the field of medicine, to achieve good medicinal value, stable quality, and high purity

Inactive Publication Date: 2016-06-01
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no public report on the introduction of a functional group benzimidazole at the 3-position of 2(1H)-quinolinone to prepare 2(1H)-quinolinone derivatives and their applications

Method used

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  • 3-benzimidazole-2(1H)-quinolinone derivative and preparation method and application thereof
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  • 3-benzimidazole-2(1H)-quinolinone derivative and preparation method and application thereof

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preparation example Construction

[0033] 1. Preparation of 1a: Mix 3.5mL of DMF and 17mL of POCl 3 After mixing and stirring evenly, add 2.03g of acetanilide, raise the temperature to 90°C, heat to reflux for 16h, pour into a large amount of ice water after cooling, and filter to obtain a yellow powder. The obtained yellow powder was mixed with 200 mL of 70% acetic acid solution, refluxed at 95° C. for 8 h, and cooled to obtain compound 1a as a yellow needle-like solid, 91%.

[0034] Compound 1a: 1 HNMR (500MHz, DMSO-d 6 )δ: 12.22(s,1H,NH),10.23(s,1H,CHO),8.49(s,1H,C=CH),7.91(d,J=7.9Hz,1H,Ar–H),7.65( t,J=7.8Hz,1H,Ar–H),7.35(d,J=8.3Hz,1H,Ar–H),7.25(t,J=8.0Hz,1H,Ar–H); 13 CNMR (126MHz, DMSO-d 6 )δ: 190.24, 161.90, 142.92, 141.60, 134.16, 131.38, 126.07, 123.14, 118.60, 115.89. MSm / z: 174[M+H] + .

[0035] 2. Preparation of 2a: Referring to the preparation steps of compound 1a, p-methylacetanilide was used instead of acetanilide to obtain compound 2a with a yield of 87%. The crystal structure is shown in th...

Embodiment 1

[0041] Example 1: 3-(5,6-dimethyl-1H-benzimidazol-2-yl)-2(1H)-quinolinone (compound 1a 1 ) preparation

[0042] Weigh 0.1g (0.58mmol) of compound 1a, 0.09g (0.64mmol) of 4,5-dimethyl-1,2-phthalate, and 6mL of anhydrous methanol and place them in a pressure-resistant test tube (sealed tube). Under the conditions of 85°C, ultrasonic frequency of 40kHz, and ultrasonic power of 540W, the reaction was complete (TLC tracking detection, about 1h). After cooling, it was filtered with suction and washed with absolute ethanol to obtain compound 1a 1 0.148g, yield 88.3%.

[0043] Compound 1a 1 : Yields88.3%, 1 HNMR (500MHz, DMSO-d 6 )δ12.42(s,2H,NH),9.05(s,1H,H-Ar),7.94(d,J=7.2Hz,1H,H-Ar),7.60(s,1H,H-Ar), 7.43(s, 3H, H-Ar), 7.28(d, J=7.5Hz, 1H, H-Ar), 2.30(s, 6H, 2CH 3 -); 13 CNMR (126MHz, DMSO-d 6 )δ161.28,147.31,138.99,138.83,131.80,129.38,123.07,120.75,119.70,115.68,20.59.MSm / z:290[M+H] + .

[0044] Therefore, it can be determined that the above compound 1a 1 It is 3-(5,6-d...

Embodiment 2

[0046] Example 2: 3-(5,6-dichloro-1H-benzimidazol-2-yl)-2(1H)-quinolinone (compound 1a 2 ) preparation

[0047] Weigh 0.1g (0.58mmol) of compound 1a, 0.11g (0.64mmol) of 4,5-dichloro-1,2-o-phenylenediamine, and 6mL of anhydrous methanol into a pressure-resistant test tube (sealed tube), at 80 Stir the reaction at ℃ until complete (TLC tracking detection, about 6h), filter with suction after cooling, and wash with absolute ethanol to obtain compound 1a 2 0.136 g, yield 71.4%.

[0048] Compound 1a 2 : Yields71.4%, 1 HNMR (500MHz, DMSO-d 6 )δ12.89(s,1H,NH),12.53(s,1H,NH),9.12(s,1H,H-Ar),7.97(d,J=7.1Hz,1H,H-Ar),7.93( s,2H,H-Ar),7.64(s,1H,H-Ar),7.45(s,1H,H-Ar),7.30(d,J=7.5Hz,1H,H-Ar); 13 CNMR (126MHz, DMSO-d 6 )δ161.26, 161.10, 153.43, 150.77, 140.59, 139.42, 132.54, 129.75, 124.91, 123.23, 119.61, 119.48, 115.81, 115.31. MSm / z: 330[M+H] + .

[0049] Therefore, it can be determined that the above compound 1a 2 It is 3-(5,6-dichloro-1H-benzimidazol-2-yl)-2(1H)-quinolinone,...

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Abstract

The invention discloses a 3-benzimidazole-2(1H)-quinolinone derivative and a preparation method and application thereof. The preparation method of the derivative includes: dissolving a 2(1H)-quinolinone derivative and an o-phenylenediamine derivative in an organic solvent, and reacting under the condition of heating to obtain the 3-benzimidazole-2(1H)-quinolinone derivative. Compared with common antitumor drug 5-FU and cisplatin, the derivative has the advantages that some derivatives in the derivative have more efficient activity, and have low toxicity on normal hepatocytes HL-7702. The 3-benzimidazole-2(1H)-quinolinone derivative is shown as in the following structural formula, wherein R1 is hydrogen, methyl and methoxyl, or forms 1,2-methylenedioxy with R2; R2 is hydrogen, or forms 1,2-methylenedioxy with the R1; R3 is hydrogen, methyl, methoxyl, fluoro, chloro, bromo, nitro or trifluoromethyl; R4 is hydrogen, methyl, methoxyl or chloro.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to 3-benzimidazole-2(1H)-quinolinone derivatives and their preparation methods and applications. Background technique [0002] Malignant tumor, also known as cancer, is one of the stubborn diseases that seriously endanger people's lives in the world. According to reports, about 7 million people die of cancer every year in the world, and about 1.5 million people die of cancer every year in my country. At the same time, due to the disadvantages of anti-tumor drugs, such as large toxic side effects and strong drug resistance, the research and development of new anti-tumor drugs has attracted people's attention. [0003] Existing studies have shown that antioxidants with excellent activity are candidate compounds for antitumor drugs (Tyagi, Y.K.; Kumar, A.; Raj, H.G.; Vohra, P.; Gupta, G.; Kumari, R.; Kumar, P. .; Gupta, R.K. Eur. J. Med. Chem. 2005, 40, 413.). In our earlier studie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D491/056A61K31/4709A61K31/4741A61P35/00
CPCC07D401/04C07D491/056
Inventor 张业邝文彬余砚成黄日镇
Owner GUILIN MEDICAL UNIVERSITY
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