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Beta-sulfonyl hydrazone derivative and preparation method and application thereof

A technology of derivatives and sulfone hydrazone, which is applied in the field of β-sulfone hydrazone derivatives and its preparation, can solve the problems of low adaptability and low yield of the group, and achieve good reaction effect and mild reaction conditions

Active Publication Date: 2021-01-08
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to expand the scope of application of the reaction, the group also studied the electrophilic addition reaction of sulfone and phenylhydrazine, but the yields of these two reactions are low, and the general adaptability of the group is not high.

Method used

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  • Beta-sulfonyl hydrazone derivative and preparation method and application thereof
  • Beta-sulfonyl hydrazone derivative and preparation method and application thereof
  • Beta-sulfonyl hydrazone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～11

[0042] The solvent of Examples 1-11 is ethanol, and different catalysts are used for the reaction, and the reaction results are shown in Table 1.

[0043] The reaction conditions and the result of table 1 embodiment 1~11

[0044]

Embodiment 12～20

[0046] The catalyzer of embodiment 12~17 adopts CuSO4.5H 2 O, the results of changing the reaction solvent are shown in Table 2.

[0047] The reaction conditions and the result of table 2 embodiment 12~17

[0048]

[0049]

[0050] The catalyzer of embodiment 18~20 adopts CuSO4.5H 2 O, the reaction solvent is water, and the results of changing the reaction temperature are shown in Table 3.

[0051] The influence of table 3 different reaction temperature on reaction

[0052]

Embodiment 21～41

[0054] The catalyzer of embodiment 21~41 adopts CuSO4.5H 2 O, water was used as the solvent, and the substrate was changed. The results obtained are shown in Table 4.

[0055] The reaction conditions and the result of table 4 embodiment 21~41

[0056]

[0057]

[0058] The structural characterization data of some products are as follows:

[0059]

[0060] N'-(1-Phenyl-2-(phenylsulfonyl)ethylene)benzenesulfonohydrazide(21):White solid,m.p:94.5-95.5℃. 1 H NMR (400MHz, CDCl 3 )δ9.59(s,1H),8.00(d,J=8.2Hz,2H),7.95-7.92(m,1H),7.90-7.88(m,1H),7.81–7.77(m,1H),7.73 –7.71(m,2H),7.68(d,J=8.2Hz,2H),7.65-7.61(m,3H),7.40-7.37(m,3H),4.55(s,2H); 13 C NMR (100MHz, CDCl 3 )δ155.41,138.31,137.60,135.15,134.79,133.43,130.21,129.55,129.08,128.44,128.32,128.15,126.41,55.80.HRMS(ESI)M / Z calcd for C 20 h 19 N 2 o 4 S 2 .[M+H] + :415.0781.Found:415.0784.

[0061]

[0062] 4-Methoxy-N'-(2-((4-methoxyphenyl)sulfonyl)-1-phenylethylidene)benzenesulfonohydrazide(27):White solid,m.p:...

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Abstract

The invention discloses a beta-sulfuryl hydrazone derivative and a preparation method and application thereof. The preparation method comprises the following steps: taking alpha-azido ketone and sulfonyl hydrazine as initial raw materials, taking CuSO4.5H2O as a catalyst, taking water as a reaction solvent, and reacting at 80 DEG C for 2-4 hours. According to the method, the catalyst CuSO4.5H2O isused in a reaction system, so that the reaction is effectively promoted, the self-coupling reaction of sulfonyl hydrazine is inhibited, and the reaction yield is increased; meanwhile, used reaction reagents and catalysts are stable, cheap and easy to obtain, large-batch production is facilitated, and a new effective way is provided for constructing the structure; and the reaction solvent is water, so that the advantages of greenness, economy and environmental protection are acheived. Therefore, the method has the characteristics of low cost, economy, environmental protection, high efficiency,wide functional group applicability and the like, and the beta-sulfuryl hydrazone compound is a widely used reaction intermediate. In addition, an activity experiment result shows that the product shows a certain degree of tumor inhibition activity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a β-sulfone hydrazone derivative and its preparation method and application. Background technique [0002] β-sulfone hydrazone compounds contain two functional groups of sulfone group and hydrazone group at the same time, which can express the multifunctionality of both, so they show good biological activities, such as anti-inflammatory, analgesic, antibacterial, anti-tuberculosis, anti-tumor etc., are deeply concerned by pharmacologists and chemists. For example: In 2014, HatemA.Abdel-Aziz and others researched new anti-inflammatory drugs and analgesic drugs, and found two compounds containing sulfone hydrazone structure (such as structural formula a and b). After 3 hours of administration, the two anti-inflammatory drugs Active ED 50 and LD 50 They were: 256±1.4μM / kg, 14.6mM / kg and 169±1.5μM / kg, 11.5mM / kg, and the analgesic activity was 2h after administration, E...

Claims

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Application Information

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IPC IPC(8): C07C317/28C07C315/00C07D333/34C07D215/36A61K31/15A61P35/00
CPCC07C315/00C07D333/34C07D215/36A61P35/00C07C317/28
Inventor 张耀红王海邓莉平罗蒙强
Owner SHAOXING UNIVERSITY
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