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2-alkyl-benzimidazole-1-acetyl hydrazone and its application

A technology of benzimidazole and acetyl, which is applied in the field of benzimidazole compounds and their derivatives, can solve the problems that the synthesis and application of benzimidazole hydrazone compounds have not been reported in literature, and achieve high atom utilization and high yield , easy-to-operate effects

Inactive Publication Date: 2012-06-27
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are no literature reports about benzimidazole hydrazone compounds and their synthesis and application.

Method used

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  • 2-alkyl-benzimidazole-1-acetyl hydrazone and its application
  • 2-alkyl-benzimidazole-1-acetyl hydrazone and its application
  • 2-alkyl-benzimidazole-1-acetyl hydrazone and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 2-methyl-benzimidazole-1-acetylhydrazide (1mmol, 0.21g) and ethanol solution (95%, 10g) to the reactor, heat and stir until the hydrazide is completely dissolved, then add salicylaldehyde (1mmol) , and finally add 0.35mmol p-toluenesulfonic acid, after adding all, heat to reflux for 5h. Finish the reaction, concentrate under reduced pressure to obtain 2-methyl-benzimidazole-1-acetyl-(N'-2-hydroxybenzyl)hydrazone, and then use ethanol-water with a volume ratio of ethanol and water of 1:4 Recrystallization gave white crystals; yield 75%; m.p.>300°C; IR(KBr): 3466(ν-O-H), 3208(ν-N-H), 1680(ν-C=O), 1614(ν-C =N), 1481 (Ar-ring), 1291 (ν-C-O); 1 H-NMR (DMSO): δ: 2.47(s, 3H), 5.03 / 5.46(s, 2H), 6.86-6.93(m, 2H), 7.13-7.18(m, 2H), 7.25-7.29(t, 1H ), 7.44-7.47(m, 1H), 7.52-7.57(m, 1H), 7.82-7.84(d, 1H), 8.38 / 8.49(s, 1H), 10.05 / 10.88(s, 1H), 1.70 / 12.07 (s, 1H); elemental analysis (C 17 h 16 N 4 o 2 ), calculated % (measured %): C: 66.21 (66.49), H: 5.24 (5.16), N: 18.17...

Embodiment 2

[0027] Add 2-methyl-benzimidazole-1-acetylhydrazide (1mmol, 0.21g) in the reactor, ethanol solution (95%, 10g), heat and stir until the hydrazide is completely dissolved, then add salicylaldehyde (1.25mmol ), and finally add 0.35mmol acetic acid, after adding all, heat to reflux for 16h. Finish the reaction, concentrate under reduced pressure to obtain 2-methyl-benzimidazole-1-acetyl-(N'-2-hydroxybenzyl)hydrazone, and then use ethanol-water with a volume ratio of ethanol and water of 1:4 Recrystallization gave white crystals; yield 36%; m.p.>300°C; IR (KBr): 3466 (ν-O-H), 3208 (ν-N-H), 1680 (ν-C=O), 1614 (ν-C =N), 1481 (Ar-ring), 1291 (ν-C-O); 1 H-NMR (DMSO): δ: 2.47(s, 3H), 5.03 / 5.46(s, 2H), 6.86-6.93(m, 2H), 7.13-7.18(m, 2H), 7.25-7.29(t, 1H ), 7.44-7.47(m, 1H), 7.52-7.57(m, 1H), 7.82-7.84(d, 1H), 8.38 / 8.49(s, 1H), 10.05 / 10.88(s, 1H), 1.70 / 12.07 (s, 1H); elemental analysis (C 17 h 16 N 4 o 2 ), calculated % (measured %): C: 66.21 (66.49), H: 5.24 (5.16), N: 18.17 (18....

Embodiment 3

[0029] Add 2-methyl-benzimidazole-1-acetylhydrazide (1mmol, 0.21g), ethanol (95%, 10g) successively in the reactor, heat and stir until the hydrazide is completely dissolved, then add salicylaldehyde (1.15mmol ), and finally added 0.35mmol HCl, after all the addition, heated to reflux for 9h. Finish the reaction, concentrate under reduced pressure to obtain 2-methyl-benzimidazole-1-acetyl-(N'-2-hydroxybenzyl)hydrazone, and then use ethanol-water with a volume ratio of ethanol and water of 1:4 Recrystallization gave white crystals; yield 52%; m.p.>300°C; IR (KBr): 3466 (ν-O-H), 3208 (ν-N-H), 1680 (ν-C=O), 1614 (ν-C =N), 1481 (Ar-ring), 1291 (ν-C-O);1 H-NMR (DMSO): δ: 2.47(s, 3H), 5.03 / 5.46(s, 2H), 6.86-6.93(m, 2H), 7.13-7.18(m, 2H), 7.25-7.29(t, 1H ), 7.44-7.47(m, 1H), 7.52-7.57(m, 1H), 7.82-7.84(d, 1H), 8.38 / 8.49(s, 1H), 10.05 / 10.88(s, 1H), 1.70 / 12.07 (s, 1H); elemental analysis (C 17 h 16 N 4 o 2 ), calculated % (measured %): C: 66.21 (66.49), H: 5.24 (5.16), N: 18.17 (...

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Abstract

The invention discloses 2-alkyl-benzimidazole-1-acetyl hydrazone and its application. The 2-alkyl-benzimidazole-1-acetyl hydrazone compound provided by the invention is 2-methyl-benzimidazole-1-acetyl-(N'-2-hydroxy benzene methylene)hydrazone, 2-methyl-benzimidazole-1-acetyl-(N'-4-hydroxy benzene methylene)hydrazone, 2-methyl-benzimidazole-1-acetyl(N'-4-dimethylamino benzoylate alkene)hydrazone, 2-methyl-benzimidazole-1-acetyl-(N'-3-nitrobenzene methylene)hydrazone, 2-methyl-benzimidazole-1-acetyl-(N'-3,4-oxymethyl methylene)hydrazone, 2-methyl-benzimidazole-1-acetyl-(N'-2-hydroxy-3,5-dibromobenzene methylene)hydrazone, 2-ethyl-benzimidazole-1-acetyl-(N'-4-hydroxy benzene methylene)hydrazone, 2-ethyl-benzimidazole-1-acetyl-(N'-4-dimethylamino benzene methylene)hydrazone or 2-ethyl-benzimidazole-1-acetyl-(N'-3,4-oxymethyl methylene)hydrazone. The above compound can be used as an antagonist for the preparation of a chemotactic factor CXCR4 acceptor and has a good effect.

Description

technical field [0001] The invention belongs to the technical field of benzazine heterocyclic compounds, and in particular relates to benzimidazole compounds and derivatives thereof. Background technique [0002] Benzimidazole compounds have good biological activity, and many benzimidazole derivatives have shown good antibacterial, antihypertensive and anticancer activities in clinical treatment. Among the benzimidazole compounds, some compounds have been found to have good pharmacological activity, such as omeprazole and lansoprazole, which can be used as proton pump inhibitors. [0003] Acylhydrazone compounds (-CONHN=CH-), which contain an imine structure, exhibit good herbicidal and bactericidal activities, and are one of the focuses in the field of pharmaceutical research. At the same time, the coordination atoms such as oxygen and nitrogen provided by acylhydrazone compounds can form acylhydrazone complexes with special structures with many metals. active. [0004] ...

Claims

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Application Information

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IPC IPC(8): A61K31/4184A61P31/04A61P31/12A61P35/00
Inventor 江银枝项卓梁大伟
Owner ZHEJIANG SCI-TECH UNIV
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