Preparation method and application of a kind of fluorine-containing oxamide homo/heteronuclear compound
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A technology of oxamide and metal compounds, applied in the application field of insecticidal active drugs, can solve the problems of unreported insecticidal activity research
Active Publication Date: 2021-05-07
WEIFANG UNIV OF SCI & TECH +1
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[0002] Since the discovery of cisplatin, transition metal compounds with targeting functions on proteins and DNA have attracted people's attention in the field of anticancer drugs. It has always attracted the attention of scientists for its unique bridging structure and the unique properties of its compounds. In recent years, more and more researchers have applied oxamide coordination compounds to the research of anticancer drugs, but in insecticidal activity Research has not been reported
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Embodiment 1
[0019] Step 1: Add 10.0mmol of 2-amino-5-fluorobenzoic acid to the reaction vessel, dissolve it with 20ml of tetrahydrofuran, dilute 12.0mmol of ethyl oxalyl chloride with 8ml of tetrahydrofuran and add it dropwise to the above solution, in an ice-water bath Reacted for 1 hour, evaporated by rotary evaporation, washed with cold ethanol, and dried under vacuum to obtain a white powdery solid. Yield: 85%.
[0021] Step 2: Dissolve 10.0 mmol of the white powder obtained in the previous step reaction in 30 ml of tetrahydrofuran, dilute 15.0 mmol of N,N-dimethyl-1,3-propanediamine with 20 ml of tetrahydrofuran in an ice-water bath, and then drop by drop The above solution was added, stirred overnight at room temperature, evaporated on a rotary basis, washed successively with cold tetrahydrofuran and cold ethanol, and dried in vacuo to obta...
Embodiment 2
[0047] Step 1: Add 10.0mmol of 2-amino-5-fluorobenzoic acid to the reaction vessel, dissolve it with 20ml of tetrahydrofuran, dilute 12.0mmol of ethyl oxalyl chloride with 8ml of tetrahydrofuran and add it dropwise to the above solution, in an ice-water bath Reacted for 1 hour, evaporated by rotary evaporation, washed with cold ethanol, and dried under vacuum to obtain a white powdery solid. Yield: 85%. 1H NMR (400MHz, DMSO) δ14.28(s, 1H), 12.47(s, 1H), 8.64-8.60(dd, J=5.2Hz, 1H), 7.79-7.76(m, 1H), 7.61-7.56( m,1H),4.35-4.29(q,2H),1.35-1.31(t,3H)
[0048] Step 2: Dissolve 10.0 mmol of the white powder obtained in the previous step reaction in 30 ml of tetrahydrofuran, dilute 15.0 mmol of N,N-dimethyl-1,3-propanediamine with 20 ml of tetrahydrofuran in an ice-water bath, and then drop by drop The above solution was added, stirred overnight at room temperature, evaporated on a rotary basis, washed successively with cold tetrahydrofuran and cold ethanol, and dried in vacuo to o...
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Abstract
The invention discloses a fluorine-containing oxamide homo / heteronuclear compound and its preparation method and application. The structural formula of the monomer and coordination polymer is as follows. The preparation method is as follows: dissolving 2 mmol of the oxamide mononuclear copper ligand in 10-20 ml In methanol, dissolve 1 mmol of the metal salt in 5-10 ml of methanol, add it to the solution of the above-mentioned mononuclear copper ligand, reflux at 60°C for 5 hours, filter, and slowly volatilize the filtrate for 1 week to obtain blue blocky crystals. It is the heteronuclear compound of fluorine-containing oxamide, the metal salts are manganese salts and copper salts, and the manganese salts are: manganese perchlorate, manganese nitrate, manganese bromide, manganese sulfate, manganese chloride, etc.; the copper The salts are: copper perchlorate, copper chloride, copper bromide, copper sulfate, etc. Compared with the platinum anti-cancer commonly used at present, the compound of the present invention has the characteristics of high anti-cancer activity, low cost, simple preparation method and the like. At the same time, it is the first time that the synthesized compound has been found to be toxic and active against Aedes albopictus, which provides a new way for the development of insecticides for related purposes.
Description
technical field [0001] The invention relates to a preparation method of a fluorine-containing oxamide homogeneous / heteronuclear compound, and the application of the compound in the preparation of anticancer drugs and insecticidal active drugs. Background technique [0002] Since the discovery of cisplatin, transition metal compounds with targeting functions on proteins and DNA have attracted people's attention in the field of anticancer drugs. It has always attracted the attention of scientists for its unique bridging structure and the unique properties of its compounds. In recent years, more and more researchers have applied oxamide coordination compounds to the research of anticancer drugs, but in insecticidal activity Research has not been reported. In addition, as an important virus transmission medium, Aedes albopictus can transmit many pathogens including dengue fever, and the eggs of Aedes albopictus have strong cold resistance and vitality, and are easy to be carrie...
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