2-aryl-1,3-dihydro-benzimidazol derivative as well as synthesis method and application thereof

A synthesis method and drug technology, applied in the field of medicine, can solve the problems that have not been seen before, and achieve the effects of good medicinal value and significant anti-renal fibrosis activity.

Active Publication Date: 2015-11-18
GUANGXI NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This type of compound has good development prospects, but there are no relevant reports on

Method used

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  • 2-aryl-1,3-dihydro-benzimidazol derivative as well as synthesis method and application thereof
  • 2-aryl-1,3-dihydro-benzimidazol derivative as well as synthesis method and application thereof
  • 2-aryl-1,3-dihydro-benzimidazol derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1) Add 1.53g (10mmol) of 4-nitro-o-phenylenediamine, 1.75g ​​(10mmol) of 2,4-dichlorobenzaldehyde, 50ml of anhydrous methanol into a 150ml round bottom flask, heat to reflux temperature and reflux for 8h . After the reaction was completed, it was cooled to room temperature, and the orange crude product was obtained by suction filtration.

[0024] 2) The crude product was subjected to silica gel column chromatography using a solvent composed of petroleum ether:dichloromethane=100:20 (volume ratio) as an eluent to obtain an orange solid product (2.85 g, yield 92%).

[0025] The resulting orange solid product is characterized by nuclear magnetic resonance, and its proton nuclear magnetic resonance spectrum and carbon spectrum are respectively as follows figure 1 and 2 shown.

[0026] 1 HNMR (500MHz, DMSO-d6) δ8.96(s, 1H), 8.45(d, J=8.5Hz, 1H), 8.00(d, J=2.5Hz, 1H), 7.95(dd, J=9.0, 2.5 Hz,1H),7.77(d,J=2.0Hz,1H),7.57(dd,J=8.5,1.7Hz,1H),6.85(s,2H),6.79(d,J=9.0Hz,1H). 13...

Embodiment 2

[0030] 1) Add 1.53g (10mmol) of 4-nitro-o-phenylenediamine, 0.88g (5mmol) of 2,4-dichlorobenzaldehyde, 50ml of absolute ethanol into a 150ml round bottom flask, heat to reflux temperature for 8h . After the reaction was completed, it was cooled to room temperature, and the orange crude product was obtained by suction filtration.

[0031] 2) The crude product was subjected to column chromatography using a solvent composed of petroleum ether:dichloromethane=100:15 (volume ratio) as an eluent to obtain an orange solid product (1.36 g, yield 88%).

[0032] The obtained orange solid product was characterized by NMR, and was determined to be 2-(2,4-dichlorophenyl)-5-nitro-1,3-dihydrobenzimidazole described in the present invention.

Embodiment 3

[0034] 1) Add 1.53g (10mmol) of 4-nitro-o-phenylenediamine, 1.75g ​​(10mmol) of 2,4-dichlorobenzaldehyde, 25ml methyl alcohol and 25ml absolute ethanol into a 150ml round bottom flask and heat to Reflux temperature reflux reaction 6h. After the reaction was completed, it was cooled to room temperature, and the orange crude product was obtained by suction filtration.

[0035] 2) The crude product was subjected to column chromatography using a solvent composed of petroleum ether:dichloromethane=100:15 (volume ratio) as an eluent, and an orange solid product (2.48 g, yield 80%) was obtained.

[0036] The obtained orange solid product was characterized by NMR, and was determined to be 2-(2,4-dichlorophenyl)-5-nitro-1,3-dihydrobenzimidazole described in the present invention.

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Abstract

The invention discloses a 2-aryl-1,3-dihydro-benzimidazol derivative as well as a synthesis method and application thereof. The synthesis method comprises the following steps: placing 4-nitro-o-phenylenediamine and 2,4-dichlorobenzaldehyde in an organic solvent for a reaction under the normal-temperature or heating condition; conducting suction filtration on the obtained reactant, so as to obtain a target crude product of the 2-aryl-1,3-dihydro-benzimidazol derivative. According to the research of the applicant in the anti-renal fibrosis and anti-chronic nephrosis activities of the 2-aryl-1,3-dihydro-benzimidazol derivative, namely a compound, the compound is remarkable in in-vitro anti-renal fibrosis activity, has a relatively high potential medicinal values, and is expected to be used for preparation of anti-renal fibrosis and anti-chronic nephrosis medicines. The compound has a chemical structure shown in the formula (I).

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 2-aryl-1,3-dihydrobenzimidazole derivative and its synthesis method and application. Background technique [0002] Chronic kidney disease is characterized by progressive loss of renal function and renal fibrosis caused by massive accumulation of extracellular matrix (ECM), mainly including glomerulosclerosis and tubulointerstitial fibrosis. Renal interstitial fibrosis is the final result of almost all chronic kidney diseases, closely related to the progression of renal failure, and is the main cause of end-stage renal failure. Early intervention and treatment of renal fibrosis will help to delay the progression of chronic kidney disease, greatly reduce the incidence of end-stage renal disease and its complications, and reduce the social and economic burden caused by it. [0003] Studies have found that transforming growth factor-β (TGF-β) and its mediated Smad signaling pathw...

Claims

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Application Information

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IPC IPC(8): C07D235/18A61P13/12
CPCC07D235/18
Inventor 彭艳刘友华卢幸洪雪
Owner GUANGXI NORMAL UNIV
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