A cinnamic acid derivative with aldose reductase inhibitory activity and its preparation method and application
A cinnamic acid derivative, a technology for inhibiting activity, applied in the field of medicine, can solve the problems of death, inaccurate curative effect, large toxic and side effects, etc.
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Embodiment 1
[0076] Example 1: Preparation of novel cinnamic acid derivatives with aldose reductase inhibitory activity
[0077] 1.1.3-N-(N-acetyl-O-benzyl-D-seryl)-α-cyano-3,4-dihydroxycinnamoylpropanediamide preparation
[0078] It includes the following five steps:
[0079] (1) Synthesis of compound α-cyano-3,4-dihydroxybenzoic acid: Weigh 138 mg (1.0 mmol) of 3,4-dihydroxybenzaldehyde into a dry 50 mL round-bottomed flask, add 85 mg of cyanoacetic acid ( 1.0 mmol), 15.4 mg (0.2 mmol) of ammonium acetate, 48 mg (0.8 mmol) of glacial acetic acid was weighed by syringe and added to the reaction system, then 10 mL of toluene was added as a solvent, and a small water separator, a condenser tube and a drying tube were connected to the reaction flask. The reaction was stirred and refluxed in an oil bath at 120°C for 18h. After the reaction was completed, the temperature was lowered to room temperature, then allowed to stand at low temperature, filtered, and the filter cake was washed three ...
Embodiment 2
[0158] Example 2: Inhibitory activity of the compound synthesized in Example 1 on aldose reductase enzyme
[0159] In this example, aldose reductase (AR), reduced coenzyme II (NADPH) and DL-glyceraldehyde were purchased from Sigma Company; Epalrestat was purchased from Tokyo Chemical Industry Co., Ltd.
[0160] Experimental steps: The enzyme reaction system was carried out on a 96-well plate. The reaction system included: PBS buffer (pH=6.2) 100 μL, 1.5 mmol / L NADPH 20 μL, 100 mmol / L DL-glyceraldehyde 20 μL, different concentrations (Epalrestat or tested sample) solution 20 μL, AR diluent 20 μL, distilled water 20 μL. The blank control group, standard control group, and enzyme metabolism group were set up in the experiment, as shown in Table 2-1.
[0161] Table 2-1. Grouping and Administration Table
[0162]
[0163] Note: All the above volume units are in μL.
[0164] After the above liquid was incubated at 37°C for 5min, except for the blank vehicle group, 20 μL of AR ...
Embodiment 3
[0172] Example 3: In vitro antioxidant activity of the compounds synthesized in Example 1
[0173] In this example, Trolox (6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylicacid); 1,1-diphenyl-2-picrylhydrazyl (DPPH) were purchased from Sigma Company.
[0174] Experimental steps: The reaction system was carried out on a 96-well plate, 40 μL of each test solution was added to the 96-well plate, and then 160 μL of DPPH solution was added in parallel to each well. At the same time, the control group (40 μL methanol + 160 μL DPPH) and the blank group (40 μL test substance + 160 μL methanol) were set. Shake for 1 min to make it evenly mixed, place the 96-well plate in the dark for 0.5 h, and quickly put the plate into the microplate reader with a detection wavelength of 517 nm. The final absorbance (A) value was measured, and each sample was tested three times in parallel, and the average value was taken. The formula for calculating the clearance rate is as follows:
[0175] Fre...
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