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N-(2-acetic acid) salicylhydrazone rare earth complex and its preparation method and use

A salicylhydrazone rare earth and salicylhydrazone technology are applied in the fields of N-(2-acetic acid) salicylhydrazone rare earth complexes and their preparation and use, and achieve the effects of strong coordination ability, good bacteriostatic activity and excellent biological activity

Inactive Publication Date: 2011-12-21
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In a large number of hydrazone compounds with biological activity, the metabolites of aroyl hydrazones are all low-toxic or non-toxic, and so far there is no information about the complexes of N-(2-acetic acid) salicylhydrazone and rare earths and their role as inhibitors. Literature reports on apple rot fungus and other crop diseases

Method used

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  • N-(2-acetic acid) salicylhydrazone rare earth complex and its preparation method and use
  • N-(2-acetic acid) salicylhydrazone rare earth complex and its preparation method and use
  • N-(2-acetic acid) salicylhydrazone rare earth complex and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 N-(2-acetic acid) salicylhydrazone (C 9 h 8 N 2 o 4 ) Synthesis

[0026] Add 46.8mL of methyl salicylate, 22.9mL of hydrazine hydrate and 23.6mL of absolute ethanol into a 250mL round-bottomed flask, stir and reflux in a water bath for 2 hours, transfer to a beaker while hot, and cool naturally, a large number of white crystals appear, after standing still, suction filter , washed with absolute ethanol. Its melting point was measured to be 145-146°C, consistent with the literature value of 145-146°C, and the yield was 72.3%.

[0027] Add 2mL of 50% glyoxylic acid dropwise to 15mL of glacial acetic acid dissolved with 2.4676g of salicylhydrazide, a pale yellow precipitate appears immediately, react in a water bath at 50°C for 1 hour, cool, and filter to obtain a light yellow powdery solid, namely N - Crude (2-acetic acid) salicylhydrazone. The powder was recrystallized with distilled water to obtain white blocky crystals. Yield: 75%, melting point 2...

Embodiment 2

[0035] Example 2 Nd(C 9 h 7 N 2 o 4 )(C 9 h 6 N 2 o 4 ) 2H 2 Synthesis of O

[0036] Weigh 1.5mmol Nd(NO 3 ) 3 4H 2 O and 3.0mmol N-(2-acetic acid) salicylhydrazone (i.e. C 9 h 8 N 2 o 4), were dissolved in 100ml water respectively, and the aqueous solution of N-(2-acetic acid) salicylhydrazone was heated to boiling, and alkali solution was added dropwise to make H 3 L is completely dissolved. Stop heating, and immediately add the aqueous solution of neodymium nitrate, at this time, white turbidity appears, and the pH is 1~2. Use lye to adjust the pH of the solution to 5-6, the solution is yellow and turbid, continue to stir and react at room temperature for 2 hours, and filter with suction to obtain a light yellow powder, wash with hot water and ethanol, dry, and constant weight to obtain the product Nd(C 9 h 7 N 2 o 4 )(C 9 h 6 N 2 o 4 ) 2H 2 O, the yield is 87%.

[0037] Elemental Analysis (%): Calculated Nd 24.26 C 36.36 H 3.05 N 9.42

[003...

Embodiment 3

[0045] Example 3 Y(C 9 h 7 N 2 o 4 )(C 9 h 6 N 2 o 4 ) 4H 2 Synthesis of O:

[0046] Weigh 1.5mmol Y(NO 3 ) 3 ·3H 2 O, 3.0mmol N-(2-acetic acid) salicylhydrazone (i.e. C 9 h 8 N 2 o 4 ), were dissolved in 100ml water respectively, the aqueous solution of N-(2-acetic acid) salicylhydrazone was heated to boiling, and alkali solution was added dropwise to make H 3 L is completely dissolved. Stop heating, and immediately add the aqueous solution of yttrium nitrate, at this time, white turbidity appears, and the pH is 1~2. Use lye to adjust the pH of the solution to 5-6. At this time, the solution is yellow and turbid. Continue to stir and react at room temperature for 2 hours, and filter with suction to obtain a light yellow powder. Wash with distilled water and ethanol, dry, and constant weight to obtain Y(C 9 h 7 N 2 o 4 )(C 9 h 6 N 2 o 4 ) 4H 2 O product, the productive rate is 86%.

[0047] Elemental Analysis (%): Calculated Y 15.45 C 37.58 H 3.85 ...

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Abstract

The invention discloses N-(2-acet)salicyloyl hydrazone-rare earth complex shown by a general structural formula (I) and a preparation method and use thereof. In the general structural formula, RE may be Pr, Nd, Eu, Dy, Yb, Er or Y; and nH2O is the crystallization water in the complex and n is between 0 and 5. The preparation of the rare earth complex comprises: heating methyl salicylate and hydrazine hydrate in a molar ratio of 1:1 in ethanol for reflux reaction to form salicylyl hydrazine; performing reflux reaction of salicyloyl hydrazine and glyoxylic acid in a molar ratio of 1:1 in glacial acetic acid to obtain N-(2-acet)salicyloyl hydrazone; and heating diluted hydrochloric acid and N-(2-acet)salicyloyl hydrazone in a molar ratio of 1:2 in aqueous solution of ethanol for reflux reaction, and obtaining the N-(2-acet)salicyloyl hydrazone-rare earth complex. In the invention, the preparation method is simple, and the prepared rare earth complex has high bacteriostatic activity on valsa mali, puccinia striiformis f. sp. tritici and the like.

Description

technical field [0001] The invention relates to N-(2-acetic acid) salicylhydrazone rare earth complex, a preparation method thereof and application of antibacterial activity. Background technique [0002] Acylhydrazones are a class of compounds with excellent biological activity, nonlinear optical properties and strong coordination ability. It can be used for antibacterial, antiviral, anti-inflammation, anti-cancer, anti-tuberculosis, etc. At the same time, its strong coordination ability enables it to form complexes with almost all metals. They can form stable chelates with metal ions in living body cells, thereby preventing many harmful enzyme reactions catalyzed by metal ions. Research has also found that in a large number of hydrazone compounds with biological activity, the metabolites of aroyl hydrazones are all low-toxic or non-toxic (Zhang Wensheng, Li Anliang. Medicinal Chemistry. Higher Education Press, Beijing, 1999, chapter three ). In 2002, people such as He S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/00A01N55/02A01P3/00
Inventor 何水样李恒欣张维萍刘峰
Owner NORTHWEST UNIV(CN)
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