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Synthesizing method for 1,3,4-selenadiazole derivative

A synthesis method and derivative technology, which can be used in drug combinations, antidote, antitumor drugs, etc., can solve problems such as unfavorable industrial production and harsh reaction conditions.

Active Publication Date: 2017-06-30
HANGZHOU JENNIFER BIOTECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic method of 1,2,5-selenodiazole is to react o-diamine with selenium dioxide, the change of the substituent is mainly in the benzene ring, the possible changes of 1,2,5-selenodiazole are too little, and the reaction conditions More stringent, not conducive to industrial production

Method used

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  • Synthesizing method for 1,3,4-selenadiazole derivative
  • Synthesizing method for 1,3,4-selenadiazole derivative
  • Synthesizing method for 1,3,4-selenadiazole derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] 2-Bromoethyl-N-phenylamino-1,3,4-selenoadiazole:

[0073]

[0074] Substituted selenourea (1mmol; or other selenourea), mixed with polyfunctional carboxylic acid compound (0.2-4mmol), mixed with 5ml POCl3 and stirred evenly; heated to 50-80°C, 5 reacted for 0.5-12h, stopped the oil bath heating, and reacted The solution was slowly poured into ice water, precipitated, separated by column chromatography, and dried; the product was obtained with a yield of 40-95%.

[0075] m / z 332 (100%, M+H + )

[0076] 1 H NMR (500MHz,) δ10.37(s, 1H), 7.65–7.53(m, 2H), 7.35(d, J=9.0Hz, 2H), 6.99(dt, J=7.4, 3.7Hz, 1H), 3.6(t, J=6.5Hz, 2H), 3.38-3.29(t, J=6.5Hz, 2H)

[0077] Experiments were carried out under different reaction conditions to obtain the following table

[0078]

[0079]

[0080] The various reactants and their reaction equations are as follows, and it should be noted that the reaction conditions in the following reactions are all within the reaction conditions...

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Abstract

The invention belongs to the field of biological medicines and specifically relates to a method and a technique forsynthesizing a bioactive poly-functional group substituted 1,3,4-selenadiazole derivative by adopting a mild condition. According to the method, a selenadiazole ring has various functional groups, so that the selenadiazole can be used as bioisosteres of thiadiazole. The requirements for the reaction conditions of thiadiazole and similar derivatives are higher, so that the method disclosed by the invention is mild in reaction condition; the selenadiazole derivative with various functional groups can be synthesized, the activity of the officinal thiadiazole compound can be further optimized and the method has significance at the aspects of development and application for new drugs.

Description

[0001] This application claims the priority of the Chinese patent application with the application number 201510929288.5 and the title of the invention "a method for synthesizing 1,3,4-selenodiazole derivatives" submitted to the China Patent Office on December 14, 2015. Its entire content is incorporated into this application by reference. technical field [0002] The invention relates to the field of biomedicine and pharmacy, in particular to a method for synthesizing 1,3,4-selenodiazole derivatives substituted by multifunctional groups with biological activity under mild conditions. Background technique [0003] Selenium-containing heterocycles have antioxidant, anti-inflammatory, antibacterial, antiviral, and antitumor effects. The anti-tumor mechanism of selenium compounds generally includes the following aspects: it has cytotoxicity, can scavenge free radicals, block the information transmission of cancer cell division and proliferation, induce cell apoptosis, regulate ...

Claims

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Application Information

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IPC IPC(8): C07D293/04C07D421/12C07D421/06A61P39/06A61P35/00
CPCC07D293/04C07D421/06C07D421/12
Inventor 阮奔放阮健昵福
Owner HANGZHOU JENNIFER BIOTECH CO LTD
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