Urea enzyme inhibitor phenyl benzyl propionyl hydroxamic acid and preparation method and use thereof
A technology of phenylbenzylpropionylhydroxamic acid and ethyl hydroxypropionate, which is applied in the field of urease inhibitor phenylbenzylpropionylhydroxamic acid and its preparation method and application, and can solve the problem of low activity and large dosage , blocking applications, etc.
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Embodiment 1
[0030] Example 1: Preparation of 3-(4-fluorobenzyl)-3-(3,4-dihydroxyphenyl)-3-hydroxypropionylhydroxamic acid (32)
[0031] Dissolve 0.7mL of p-fluorophenylacetyl chloride in 20mL of anhydrous ether, then add 1.1g of 1,2-benzenediol and 3g of ketone trifluoromethanesulfonate, stir at 90°C for 22h, cool, and pour into Put 10g of crushed ice and 5g of 30% concentrated hydrochloric acid into a beaker, stir for 30min, keep the layers static, extract the aqueous phase twice with a small amount of benzene, and combine the organic phases. Concentrate, add absolute ethanol and 5% activated carbon to reflux for 30 minutes, filter while hot, add petroleum ether, and cool to obtain 2.19 g of white crystal 3,4-dihydroxy-4'-fluorodeoxybenzoin, with a yield of 89%. Then take 738mg 3,4-dihydroxy-4'-fluorodeoxybenzoin, 1.9gZn, 1.1gNH 4 Cl and 1.3mL ethyl bromoacetate were ground together, left to stand for 8h, poured into 100mL saturated NH 4 Cl solution and then extracted with AcOEt, anhyd...
Embodiment 2
[0033] According to the method similar to Example 1, the phenylbenzylpropionyl hydroxamic acid series compounds 1-80 listed in Table 1 were synthesized by using different substituted forms of deoxybenzoin as raw materials.
[0034] Each R group of phenylbenzyl propionyl hydroxamic acid series compound in the general formula I of table 1
[0035] serial number
[0036] serial number
[0037] serial number
[0038] serial number
[0039] Note: The initial raw materials were purchased from aldrich company
Embodiment 3
[0040] Embodiment 3: the inhibitory enzyme activity of compound
[0041] Add 25 μL of Jack bean urease (4U) and 25 μL (1 mM) of the test compound solution to the 96-well plate, incubate at 37 °C for 2 h, then add 55 μL of phosphate buffer containing 100 mM urea and 100 mM, and incubate at 30 °C. Incubate at ℃ for 15 min, add 45 μL of phenol reagent (mixed solution containing 1% phenol and 0.005% sodium nitroprusside) and 70 μL alkali reagent (mixed solution of NaOCl containing 0.5% NaOH and 0.1% active chlorine), at room temperature After standing for 50 minutes, measure the OD value at 630nm with a microplate reader, and the percentage inhibition rate is calculated according to the following formula:
[0042]
[0043] All experiments were performed in solutions at pH 8.2 (0.01M K 2 HPO 4 , 1mM EDTA, 0.01M LiCl), the level of activity is measured by the half-inhibition rate IC 50 to indicate that the IC 50 The smaller the value, the higher the activity of the compound. ...
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