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Hydroxyl and alkoxyl benzaldehyde indole Schiff bases, preparation method thereof, and application thereof

A technology of alkoxybenzaldehyde and indole Schiff base, applied in the field of Schiff base preparation, can solve the problems of unfavorable popularization and application, low anticancer activity, low water solubility, etc., achieve low cost, inhibit proliferation, The effect of simple reaction process

Inactive Publication Date: 2012-06-13
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the medical field, Schiff bases have antibacterial, bactericidal, antitumor, and antiviral biological activities; existing amino acid Schiff bases, guanidine Schiff bases, etc. have anticancer activity, and these compounds have relatively low anticancer activity Low, and generally have the disadvantages of high toxicity and low water solubility. At present, most of the suspensions are used for antibacterial and anticancer activity tests, which is not conducive to their clinical promotion and application.

Method used

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  • Hydroxyl and alkoxyl benzaldehyde indole Schiff bases, preparation method thereof, and application thereof
  • Hydroxyl and alkoxyl benzaldehyde indole Schiff bases, preparation method thereof, and application thereof
  • Hydroxyl and alkoxyl benzaldehyde indole Schiff bases, preparation method thereof, and application thereof

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Embodiment 1

[0026] Embodiment 1 This embodiment provides the preparation of 2-hydroxybenzaldehyde indole Schiff base:

[0027] Measure 60 mL of ethanol as a solvent in the reactor, add 0.50 g of 2-hydroxybenzaldehyde and 0.9 g of aminoindole compound into the reactor, stir well, heat to reflux, and react for about 6 hours. After the reaction, the solution in the reactor was evaporated to obtain the crude product, and the mixture of ethyl acetate:petroleum ether (60-90° C.)=1:1 was recrystallized to obtain the pure product with a yield of 87.5%.

[0028] Hydrogen spectrum of the crystalline product:

[0029] 1 H NMR (300MHz, DMSO-d6, δ): 13.41(s, 1H, OH), 11.84(s, 1H, NH), 9.06(s, 1H, ArH), 8.03(d, 1H, ArH, J=8.7 Hz), 7.95 (d, 1H, ArH, J=8.7Hz), 7.53-6.96 (m, 4H, ArH), 4.29 (q, 2H, CH 2 , J=7.20Hz), 2.68(s, 3H, CH 3 ), 1.36(t, 3H, CH 3 , J=7.20Hz).

[0030] Spectrum such as figure 1 .

Embodiment 2

[0031] Embodiment 2 This embodiment provides the preparation of 3-hydroxybenzaldehyde indole Schiff base:

[0032] Measure 60mL of ethanol as a solvent in the reactor, add 0.62g of 3-hydroxybenzaldehyde and 11g of aminoindole compound into the reactor, stir well, heat to reflux, and react for about 7 hours. After the reaction, the solution in the reactor was evaporated to obtain the crude product, and the pure product was obtained by recrystallization from ethyl acetate:petroleum ether (60-90° C.) = 1:1 mixture with a yield of 92.7%.

Embodiment 3

[0033] Embodiment 3 This embodiment provides the preparation of 4-hydroxybenzaldehyde indole Schiff base:

[0034] Measure 60mL of ethanol as a solvent in the reactor, add 0.73g of 4-hydroxybenzaldehyde and 1.3g of aminoindole compound into the reactor, stir well, heat to reflux, and react for about 5 hours. After the reaction, the solution in the reactor was evaporated to obtain the crude product, and the mixture of ethyl acetate:petroleum ether (60-90° C.)=1:1 was recrystallized to obtain the pure product with a yield of 79.6%.

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Abstract

The invention relates to hydroxyl and alkoxyl benzaldehyde indole Schiff bases, a preparation method thereof, and an application thereof. The structures of the Schiff bases are represented by the following (1), (2) or (3). Substituents are defined in the specification. The preparation method comprises steps that: ethanol is adopted as a solvent, and is placed in a reactor; hydroxyl or alkoxyl benzaldehyde is added into the reactor; an aminoindole compound with a molecular weight equaling to that of the hydroxyl or alkoxyl benzaldehyde is added into the reactor; the materials are completely dissolved, and a temperature is controlled at 60-80 DEG C; heating and refluxing are carried out, and a reaction is carried out for 4-8h; a solution in the reactor is evaporated, such that a crude product is obtained; and a finished product is obtained through recrystallization. The product provided by the invention assists in effectively inhibiting the proliferations of various tumor cell strains, and has good water-solubility.

Description

technical field [0001] The invention relates to a preparation method of Schiff base, in particular, condensing hydroxyl or alkoxy benzaldehyde and aminoindole to synthesize Schiff base. Background technique [0002] Schiff bases mainly refer to a class of organic compounds containing imine or amethanimine characteristic groups (-RC=N-), and Schiff bases are usually formed by condensation of amines and active carbonyl groups. [0003] Important applications of Schiff base compounds and their metal complexes in the fields of medicine, catalysis, analytical chemistry, corrosion and photochromism. In the field of catalysis, the cobalt and nickel complexes of Schiff bases have been used as catalysts; in the field of analysis, Schiff bases, as good ligands, can be used to identify, identify and quantitatively analyze the content of metal ions; in the field of corrosion , some aromatic Schiff bases are often used as copper corrosion inhibitors; in the field of photochromism, some ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/42A61K31/404A61P35/00
Inventor 曹成波王名扬万茂生
Owner SHANDONG UNIV
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