Application of N-substituted aryl (arylformamido)-N'-substituted arylformyl thiourea compound in inhibition of blue alga growth
A technology of arylformylthiourea and arylformylamino, which is applied in the application field of N-substituted aryl (arylformylamino)-N'-substituted arylformylthiourea compounds in the growth inhibition of cyanobacteria, and can Solve the problem that cyanobacteria cannot grow, and achieve the effect of good inhibition effect
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Embodiment 1
[0033] Example 1 Take JL2016ly40 as an example to synthesize the steps of compound I series
[0034] Step 1: Synthesis of substituted benzoyl isothiocyanate
[0035] Dissolve 230 mg of KSCN in 5 mL of acetone, stir at room temperature until the KSCN is completely dissolved, add 1 times equivalent of substituted benzoyl chloride dropwise, at which time a white precipitate will precipitate. Then reflux for 2h at 40-50℃, filter with suction after cooling, retain the filtrate, and use it directly in the second step reaction;
[0036] Step 2: Synthesis of the target product
[0037] Dissolve 500 mg of 2-hydroxyaniline in 15 mL of acetone and stir at room temperature until the aniline is dissolved. After the dissolution is complete, the filtrate obtained in the first step is added dropwise to the acetone solution of 2-hydroxyaniline and stirred at room temperature for 5 minutes; at this time, a precipitate will precipitate at the bottom of the solution. After refluxing for 3 hours, the 2-...
Embodiment 2
[0089] Example 2 Taking JL2016ly75 as an example to synthesize compound Ⅱ series
[0090] Step 1: Synthesis of substituted benzoyl isothiocyanate
[0091] Dissolve 230 mg of KSCN in 5 mL of acetone, stir at room temperature until the KSCN is completely dissolved, add 1 times equivalent of substituted benzoyl chloride dropwise, at which time a white precipitate will precipitate. Then reflux for 2h at 40-50℃, filter with suction after cooling, retain the filtrate, and use it directly in the second step reaction;
[0092] Step 2: Synthesis of the target product
[0093] Dissolve 500 mg of phenylhydrazine in 20 mL of acetone, and add the filtrate obtained in the first step to the acetone solution of phenylhydrazine dropwise. At this time, the color of the solution will change. Reflux for 3h. After monitoring the completion of the phenylhydrazine reaction by TLC, after cooling, suction filtration. Add 50 mL of ice water to the filtrate and stir at room temperature for 30 min. A large am...
Embodiment 3
[0141] In the following, Example 3 is used to specifically illustrate the activity of the compounds of formula I and formula II of the present invention on fructose 1,6-bisphosphate aldolase.
[0142] The cyanobacteria fructose 1,6-bisphosphate aldolase enzyme inhibition test was performed 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 to 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 in the absorbance of NADH at 340nm, a...
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