Urea enzyme inhibitor flavone hydroxamic acid compounds and preparation methods and uses thereof
A technology of flavone hydroxamic acid and flavone hydroxamic acid, which is applied in the field of urease inhibitors, can solve problems such as hindering application, low activity, instability, etc., and achieve a good effect of inhibiting activity
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Embodiment 1
[0030] Example 1: Preparation of 2-(2-(4-hydroxy-3-chlorophenyl)-4,5,7-trihydroxy-4H-benzopyran-4-yl)acetylhydroxamic acid (5)
[0031] Dissolve 16.8g of 2,4,6-trihydroxyacetophenone and 17.2g of 3-chloro-4-hydroxybenzaldehyde in 150mL of EtOH solution containing 12.9g of KOH, raise the temperature to 65°C under stirring, react for 12h, after cooling After suction filtration, the solid was washed with water to obtain 26.7 g of the product 2,4,6,4'-tetrahydroxy-3'-chloro-chalcone with a yield of 87%. Dissolve 15.3 g of the obtained chalcone in 50 mL of DMSO, add 1.3 g of iodine, raise the temperature to 100 °C under stirring, react for 8 h, cool, add 150 mL of water, collect the precipitate, and wash with water to obtain 5,7,4'-tri Hydroxy-3'-chloroflavone 11.6g, yield 76%;
[0032] 6.1g 5,7,4'-trihydroxy-3'-chloroflavone, 13gZn, 9.6gNH 4 Cl and 6.7mL of ethyl bromoacetate were ground together, left to stand for 15h, poured into 100mL of saturated NH 4 Cl solution and then e...
Embodiment 2
[0034] Flavone hydroxamic acid series compounds 1-50 listed in Table 1 were synthesized in the same manner as in Example 1, using flavones in different substituted forms as raw materials.
[0035] Each R group of flavone hydroxamic acid series compounds in the general formula I of table 1
[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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