Synthesis and Biological Activity Evaluation of Shikonin Benzoyl Acrylic Acid Carboxylate Derivatives
A technology of benzoyl acrylic acid carboxylic acid and derivatives, which can be used in drug combination, organic chemistry, anti-tumor drugs, etc., can solve problems such as unfavorable clinical application and high molecular toxicity, and achieve low toxic side effects and obvious tumor cell inhibitory activity. Effect
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example 1
[0025] Example 1: Preparation of Shikonin Benzoyl Acrylic Acid Carboxylate Derivatives
[0026] Chemical synthesis route
[0027] Reaction of benzene or benzene derivatives with maleic anhydride to obtain intermediate benzoyl acrylic acid molecules, and esterification of the obtained benzoyl acrylic acid intermediates with shikonin to obtain target molecule shikonin derivatives.
[0028] chemical synthesis steps
[0029] Synthesis of Intermediates
[0030] (E)-4-(2,5-dimethylphenyl)-4-oxobut-2-enoic acid (1a)
[0031] Dissolve the maleic anhydride of 0.02mol anhydrous aluminum chloride and 0.01mol of the catalyst in a 40mL flask, stir at room temperature for 10min, so that the anhydrous aluminum chloride and maleic anhydride can be fully dissolved, subsequently, 0.01mol P-xylene was slowly added dropwise to the solution system, and the color of the solution gradually changed to yellowish brown. The above reaction system was stirred at room temperature for 12 h, and the pro...
example 2
[0052] Example 2: Application of Formula I Shikonin Lipoic Acid Ester Derivatives
[0053] H460, HeLa, MCF-7, A549 cell lines were used as detection strains, and MTT colorimetric method was used as detection method. Through research on the tumor cell inhibitory activity of Shikonin carboxylate derivatives of formula I in vitro, it was found that this type of novel structure The derivatives have obvious tumor cell inhibitory activity in vitro and have low toxicity to normal cells. see attached results figure 1 , 2 , 3, 4.
example 3
[0054] Example 3: Compound 7 induces apoptosis of A549 cells
[0055] attached Figure 5 It was shown that after compound 7 was treated with drug concentrations of 0, 2, 4, 8, and 12 μM for 24 hours, it can be concluded that, at the same time, with the continuous increase of drug concentration, the apoptosis rate of A549 cells increased significantly. The proportion of early apoptotic cells increased from 1.15% to 42.6%, and the proportion of late apoptotic cells increased from 5.69 to 38.1%. At the same time, there was no significant change in the proportion of broken cells that had an impact on the experimental results. It can be concluded that compound 7 has a concentration-dependent effect on promoting apoptosis of A549 cells.
[0056] Effect of compound 7 on time-dependent apoptosis of A549 cells. From attached Figure 6 As shown in , A549 cells were treated with 8 μM compound PMMB-135 for 12h, 24h and 36h. The proportion of early apoptotic cells increased from 2.02%...
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