Synthetic method for 2-substitutied benzimidazole ring derivatives through enzyme catalysis

A synthesis method and technology of benzimidazole are applied in the field of synthesizing 2-substituted benzimidazole ring derivatives, which can solve the problems of complicated operation and severe reaction conditions, achieve good yield, short reaction time, and reduce acidity and alkalinity. Effects of the use of substances and metals

Active Publication Date: 2014-03-12
杭州新拜思生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods have disadvantages such as complicated operation and severe reaction conditions.

Method used

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  • Synthetic method for 2-substitutied benzimidazole ring derivatives through enzyme catalysis
  • Synthetic method for 2-substitutied benzimidazole ring derivatives through enzyme catalysis

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Experimental program
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Embodiment 1

[0022] Embodiment 1: the synthesis of 2-(2-chloro-phenyl)-benzimidazole

[0023] Add about 0.5 mmol of o-phenylenediamine, about 0.5 mmol of o-chlorobenzaldehyde, 3 mL of ethanol, and about 0.035 g of lipase (Lipase AY30) into a 10 mL test tube, and shake the reaction at 35°C for about 5 hours to After the reaction was completed, the clear liquid was collected by centrifugation for precipitation, and the crude product was recrystallized from ethanol to obtain 0.11 g of the compound with a yield of 93%.

[0024] Product characterization: Mp: 275.6-278.8℃. IR(KBr) 3375,1654,1536,1520,1345. 1 H NMR (400 MHz, DMSO-d6), δ 13.02 (s, 1H), 8.30 (d, 2H, J=8 Hz), 7.75(m, 2H), 7.56 (d, 1H, J=8 Hz), 7.48(d, 1H, J=8 Hz), 7.22(m, 1H), 7.14(m, 1H). MS (EI):m / z=228.

Embodiment 2

[0025] Embodiment 2: the synthesis of 2-(2-chloro-phenyl)-benzimidazole

[0026] Add about 0.5 mmol of o-phenylenediamine, about 0.5 mmol of o-chlorobenzaldehyde, 3 mL of ethanol, and about 0.035 g of porcine pancreatic amylase (α-Amylase from hog pancreas) into a 10 mL test tube, at a temperature of 35 °C The reaction was shaken for about 5 hours to the end of the reaction, and the clear liquid was taken by centrifugation for precipitation. The crude product was recrystallized from ethanol to obtain 0.088 g of the compound, with a yield of 77%.

[0027] Product characterization: Mp: 275.6-278.8℃. IR(KBr) 3375,1654,1536,1520,1345. 1 H NMR (400 MHz, DMSO-d6), δ 13.02 (s, 1H), 8.30 (d, 2H, J=8 Hz), 7.75(m, 2H), 7.56 (d, 1H, J=8 Hz), 7.48(d, 1H, J=8 Hz), 7.22(m, 1H), 7.14(m, 1H). MS (EI):m / z=228.

Embodiment 3

[0028] Embodiment 3: the synthesis of 2-(2-chloro-phenyl)-benzimidazole

[0029] In a 10 mL test tube, add about 0.5 mmol of o-phenylenediamine, about 0.5 mmol of o-chlorobenzaldehyde, 3 mL of ethanol, and about 0.035 g of α-Amylase from Aspergillus oryzae, at a temperature of 35°C The reaction was shaken for about 5 hours to the end of the reaction, and the clear liquid was taken by centrifugation for precipitation. The crude product was recrystallized from ethanol to obtain 0.060 g of the compound with a yield of 41%.

[0030] Product characterization: Mp: 275.6-278.8℃. IR(KBr) 3375,1654,1536,1520,1345. 1 H NMR (400 MHz, DMSO-d6), δ 13.02 (s, 1H), 8.30 (d, 2H, J=8 Hz), 7.75(m, 2H), 7.56 (d, 1H, J=8 Hz), 7.48(d, 1H, J=8 Hz), 7.22(m, 1H), 7.14(m, 1H). MS (EI):m / z=228.

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Abstract

The invention discloses a synthetic method for 2-substitutied benzimidazole derivatives shown in the formula (I) through enzyme catalysis. The synthetic method is as follows: o-phenylenediamine, R-CHO are employed as reactants and reacted through enzyme catalysis in organic solvents, and 2-substitutied benzimidazole derivatives are obtained. The enzyme is selected from one of alpha-Amylase from hog pancreas, Diastase from Aspergillus oryzae, alpha-Amylase from Aspergillus oryzae, Lipase AT30, Lipase AY30, and Trypsin NB from porcine pancreas. The method has mild reaction conditions and high yield, and is environmentally friendly.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing 2-substituted benzimidazole ring derivatives. (2) Background technology [0002] Imidazole and its derivatives have proton-accepting properties, conjugated acid-base properties, and complex coordination properties, and enjoy the reputation of "biocatalyst" and "bioligand". In nature, imidazole, as the active center functional group of many enzymes, participates in important biochemical reactions and plays a very important role in life activities. Many drugs, enzyme inhibitors, etc. also contain imidazole central functional groups. At the same time, it is a common heterocyclic compound in natural products and medicines. It has a variety of biological activities and pharmacological activities. Its biological activities such as antibacterial, antiviral, and anti-inflammatory are very significant in medicine. It is also commonly used in epoxy resin curing (promoting) agents. , urethane catalyst, copp...

Claims

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Application Information

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IPC IPC(8): C12P17/10C12P17/16
Inventor 郑辉施巧月杜奎梅怡嘉章鹏飞
Owner 杭州新拜思生物医药有限公司
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