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A kind of β-sulfone hydrazone derivative and its preparation method and application

A technology of derivatives and sulfone-based hydrazones, applied in the field of beta-sulfone-based hydrazone derivatives and their preparation, can solve the problems of poor general adaptability of groups, low yields and the like, and achieves good reaction effect, mild reaction conditions, and reaction Reagent stable and easy to obtain effect

Active Publication Date: 2021-12-10
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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  • A kind of β-sulfone hydrazone derivative and its preparation method and application
  • A kind of β-sulfone hydrazone derivative and its preparation method and application
  • A kind of β-sulfone hydrazone derivative and its preparation method and application

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 β-sulfone hydrazone derivative and its preparation method and application. The preparation method comprises the following steps: using α-azide and sulfonyl hydrazide as starting materials, using CuSO 4 . 5H 2 O is a catalyst, water is a reaction solvent, the reaction temperature is 80° C., and the reaction time is 2-4 hours. The present invention uses catalyst CuSO in the reaction system 4 . 5H 2 O, effectively promoted this reaction, suppressed the self-coupling reaction of sulfonyl hydrazine, improved the yield of reaction; Simultaneously, used reaction reagent and catalyzer are stable cheap and easy to get, be convenient to carry out mass production, for constructing this The class structure provides a new effective way; and the reaction solvent is water, which has the advantages of green economy and environmental protection. Therefore, the method has the characteristics of low cost, economy, environmental protection, high efficiency, wide applicability of functional groups, etc., and β-sulfone hydrazone compounds are widely used reaction intermediates. In addition, the results of activity experiments showed that the product exhibited a certain degree of tumor suppressive 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/34
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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