Application of n-Substituted Aryl(Aramido)-n'-Substituted Aroylthiourea Compounds in Growth Inhibition of Cyanobacteria
An arylformyl thiourea and arylformylamino technology, which is applied to the application field of N-substituted aryl (arylformylamino)-N'-substituted arylformyl thiourea compounds in the inhibition of cyanobacterial growth, and can Solve the problem that cyanobacteria cannot grow, and achieve the effect of good inhibition effect
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Embodiment 1
[0039] Example 1 Take JL2016ly40 as an example to synthesize the steps of compound I series
[0040] Step 1: Synthesis of Substituted Benzoyl Isothiocyanates
[0041] Dissolve 230mg of KSCN in 5mL of acetone, stir at room temperature until KSCN is completely dissolved, then add 1 times the equivalent of substituted benzoyl chloride dropwise, and a white precipitate will precipitate. Then reflux at 40-50°C for 2 hours, suction filter after cooling, keep the filtrate, and directly use it in the second step reaction;
[0042] The second step: the synthesis of the target product
[0043] Dissolve 500mg of 2-hydroxyaniline in 15mL of acetone and stir at room temperature until the aniline is dissolved. After the dissolution is complete, add the filtrate obtained in the first step to the acetone solution of 2-hydroxyaniline dropwise, and stir at room temperature for 5 minutes; at this time, a precipitate will precipitate at the bottom of the solution. After it was refluxed for 3 h...
Embodiment 2
[0092] Example 2 Taking JL2016ly75 as an example to synthesize the steps of compound II series
[0093] Step 1: Synthesis of Substituted Benzoyl Isothiocyanates
[0094] Dissolve 230mg of KSCN in 5mL of acetone, stir at room temperature until KSCN is completely dissolved, then add 1 times the equivalent of substituted benzoyl chloride dropwise, and a white precipitate will precipitate. Then reflux at 40-50°C for 2 hours, suction filter after cooling, keep the filtrate, and directly use it in the second step reaction;
[0095] The second step: the synthesis of the target product
[0096] Dissolve 500mg of benzohydrazide in 20mL of acetone, and add the filtrate obtained in the first step to the solution of benzohydrazide in acetone dropwise, and the color of the solution will change at this time. Reflux for 3h. After the completion of the benzoyl hydrazide reaction was monitored by TLC, after cooling, suction filtration was performed. Add 50 mL of ice water to the filtrate, ...
Embodiment 3
[0144] The activity of the compound of formula I and formula II of the present invention on fructose 1,6-bisphosphate aldolase is specifically illustrated by Example 3 below.
[0145] The cyanobacterial fructose 1,6-bisphosphate aldolase enzyme inhibition test was carried out on the compounds synthesized above. Fructose-1,6-bisphosphate aldolase can reversibly decompose fructose-1,6-bisphosphate into dihydroxyacetone phosphate and glyceraldehyde-3-phosphate. Under the action of triose phosphate isomerase (TIM), dihydroxyacetone phosphate can be converted into glyceraldehyde-3-phosphate. Finally, glyceraldehyde-3-phosphate is converted into glycerol-3-phosphate under the action of glyceraldehyde-3-phosphate dehydrogenase (GPDH), and at the same time, two molecules of NADH (nicotinamide adenine dinucleotide) are converted into NAD+. Therefore, the activity of fructose-1,6-bisphosphate aldolase can be measured by measuring the change of the absorbance value of NADH at 340nm, and...
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