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2-chlorine-3-(1H-benzimidazole-2-radical)-quinoline derivative and preparation method and application thereof

A chlorine-based and methyl-based technology, applied in the field of medicine, achieves the effects of simple post-processing, improved anti-tumor activity, and good medicinal value

Inactive Publication Date: 2016-07-06
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no public report on the introduction of a functional group benzimidazole at the 3-position of the quinoline skeleton to prepare 2-chloro-3-(1H-benzimidazol-2-yl)-quinoline derivatives

Method used

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  • 2-chlorine-3-(1H-benzimidazole-2-radical)-quinoline derivative and preparation method and application thereof
  • 2-chlorine-3-(1H-benzimidazole-2-radical)-quinoline derivative and preparation method and application thereof
  • 2-chlorine-3-(1H-benzimidazole-2-radical)-quinoline derivative and preparation method and application thereof

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Effect test

preparation example Construction

[0033] 1. Preparation of Compound 1: Mix 3.5mL of DMF and 17mL of POCl 3 After mixing and stirring evenly, 2.03 g of acetanilide was added, the temperature was raised to 90° C., heated to reflux for 16 hours, cooled and poured into a large amount of ice water, and filtered to obtain compound 1 with a yield of 88%.

[0034] Compound 1: 1 HNMR (500MHz, DMSO-d 6)δ: 10.49(s,1H,CHO),8.79(s,1H,C=CH),8.11(d,J=7.9Hz,1H,Ar–H),7.95(t,J=7.8Hz,1H, Ar–H),7.89(d,J=8.3Hz,1H,Ar–H),7.68(t,J=8.0Hz,1H,Ar–H); MSm / z:192[M+H] + .

[0035] 2. Preparation of compound 2: Referring to the synthetic procedure of compound 1, p-methylacetanilide was used instead of acetanilide to obtain compound 2 with a yield of 85%.

[0036] Compound 2: 1 HNMR (500MHz, DMSO-d 6 )δ:10.61(s,1H,CHO),8.80(s,1H,C=CH),8.12(d,J=7.8Hz,1H,Ar–H),8.01(t,J=7.9Hz,1H, Ar–H),7.75(d,J=8.3Hz,1H,Ar–H),2.61(s,CH3); MSm / z:206[M+H] + .

[0037] 3. Preparation of compound 3: Referring to the synthesis procedure of compound 1, p-meth...

Embodiment 1

[0041] Example 1: Preparation of 2-chloro-3-(5,6-dimethyl-1H-benzimidazol-2-yl)-6-methoxyquinoline (compound a)

[0042] Weigh 30.2g (0.90mmol) of the compound, 0.122g (0.90mmol) of 4,5-dimethyl-o-phenylenediamine, and 6mL of anhydrous methanol into a pressure-resistant test tube (sealed), and stir the reaction at 80°C To complete (TLC tracking detection, about 9h), after cooling, filter with suction and wash with absolute ethanol to obtain 0.179 g of compound a (light yellow solid), with a yield of 59%.

[0043] Compound a: Yields59%, 1 HNMR (500MHz, DMSO-d 6 )δ12.88(s,1H),8.84(s,1H),7.96(d,J=9.2Hz,1H),7.60(s,1H),7.55(d,J=9.1Hz,1H),7.46( s,2H),3.93(s,3H),2.36(s,6H); 13 CNMR (126MHz, DMSO-d 6 )δ158.70, 147.27, 144.89, 143.27, 140.29, 131.65, 129.64, 128.16, 125.06, 124.67, 106.81, 56.24, 20.49. MSm / z: 338[M+H] + .

[0044] Therefore, it can be determined that the above-mentioned compound a is 2-chloro-3-(5,6-dimethyl-1H-benzimidazol-2-yl)-6-methoxyquinoline, and its stru...

Embodiment 2

[0046] Example 2: 2-chloro-3-(5,6-dimethyl-1H-benzimidazol-2-yl)-[1,3]dioxolane[6,7-g]quinoline ( Preparation of compound b)

[0047] Weigh 40.2g (0.85mmol) of the compound, 0.116g (0.85mmol) of 4,5-dimethyl-o-phenylenediamine, and 6mL of anhydrous methanol into a pressure-resistant test tube (sealed), and stir the reaction at 80°C To complete (TLC tracking detection, about 7.5h), after cooling, filter with suction, wash with absolute ethanol to obtain 0.192g of compound b (light yellow solid), with a yield of 64.5%.

[0048] Compound b: Yields64.5%, 1 HNMR (500MHz, DMSO-d 6 )δ12.19(s, 1H), 8.75(s, 1H), 7.54(s, 1H), 7.44(d, J=5.6Hz, 3H), 6.29(s, 2H), 2.35(s, 6H); 13 CNMR (126MHz, DMSO-d 6 )δ152.94, 149.07, 147.41, 145.96, 145.09, 140.00, 131.45, 124.15, 122.76, 104.53, 103.47, 103.20, 20.4. MSm / z: 352[M+H] + .

[0049] Therefore, it can be determined that the above compound b is 2-chloro-3-(5,6-dimethyl-1H-benzimidazol-2-yl)-[1,3]dioxolane[6,7-g ] quinoline, its structu...

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Abstract

The invention discloses a 2-chlorine-3-(1H-benzimidazole-2-radical)-quinoline derivative and a preparation method and application thereof.The preparation method of the derivative includes the steps that a 2-chlorine-3-formaldehyde quinoline derivative and an o-phenylendiamine derivative are taken and dissolved in organic solvent, a reaction is conducted under the heating condition, and the 2-chlorine-3-(1H-benzimidazole-2-radical)-quinoline derivative is obtained.Certain derivative bodies in the derivative are higher in activity compared with a common antitumor drug 5-FU and cis-platinum and lower in toxicity to normal hepatocytes HL-7702.The 2-chlorine-3-(1H-benzimidazole-2-radical)-quinoline derivative is of the structure as shown in the formula (I), wherein R1 is hydrogen, methyl, methoxy group or forms 1, 2-methylenedioxy with R2; R2 is hydrogen or forms 1, 2-methylenedioxy with R1; R3 is hydrogen, methyl, methoxy group, fluorine group, chlorine group, bromine group, nitryl or trifluoromethyl; R4 is hydrogen, methyl, methoxy group or chlorine group.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a preparation method and application of 2-chloro-3-(1H-benzimidazol-2-yl)-quinoline derivatives. Background technique [0002] Cancer is one of the stubborn diseases that seriously endanger people's lives. The development of drugs to prevent and treat cancer is one of the worldwide problems that scientists need to overcome. [0003] Quinolines are an important class of nitrogen heterocyclic compounds. Studies have shown that quinoline and its derivatives have broad-spectrum biological activities such as anti-oxidation, anti-tumor, anti-inflammation, and anti-malarial, so the design and synthesis of quinoline derivatives has received people's attention (DeRuiter, J.Brubaker, A.N.; Whitmer, W.L.; Stein, J.L.; J.Med.Chem.1986, 29, 2024.; Zhang, Y.; Yi, X.H.; Peng, Y. Bioorg. Med. Chem. 2013, 23, 107.; Hewawasam, P.; Fan, W.; Knipe, J.; . Med. Chem. Lett. 2002, 12, 1779.). Benzi...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D491/056A61K31/4709A61K31/4741A61P35/00
CPCC07D401/04C07D491/056
Inventor 张业邝文彬余砚成
Owner GUILIN MEDICAL UNIVERSITY
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