新型肉桂酰胺衍生物的合成及其抑制酪氨酸酶活性的研究

Synthesis of Novel Cinnamamide Derivatives and Inhibition of Tyrosinase Activity

目的:肉桂酰胺类化合物具有抑制酪氨酸酶活性、促进细胞调亡、降低血压、增强免疫、抗氧化等多种生物活性。本文设计合成了一系列肉桂酰胺衍生物,并对其抑制酪氨酸酶活性进行初步的评价。方法:以不同的取代苯甲醛为原料,经过羟基的保护、烯化、水解、缩合等化学反应合成目标产物。以曲酸为阳性对照,评估了合成化合物对酪氨酸酶的抑制活性。结果:合成了10个化合物,其中4个化合物未见相关文献报道,其结构经核磁共振氢谱(^(1)H NMR)、核磁共振碳谱(^(13)C NMR)和质谱(LRMS)等确证。对设计、合成的10个肉桂酰胺衍生物进行了酪氨酸酶的抑制作用的评价,其中2个化合物在25μmol·L^(-1)浓度下具有明显的酪氨酸酶抑制活性。

Objective: Cinnamamide compounds have many biological activities, such as Inhibition of tyrosinase activity, promoting cell apoptosis, reducing blood pressure, enhancing immunity, antioxidation and so on. In this paper, a series of cinnamamide derivatives were designed and synthesized, and their tyrosinase inhibitory activities were evaluated. Methods: The target product was synthesized from different substituted benzaldehydes through the protection of hydroxyl group, Olefination, hydrolysis, condensation and other chemical reactions. Using kojic acid as positive control, the inhibitory activity of the synthesized compounds on tyrosinase was evaluated. Results: Ten compounds have been synthesized, four of which have not been reported in literature. Their structures have been confirmed by ^(1)H NMR, ^(13)C NMR and LRMS. Ten cinnamamide derivatives were designed and synthesized and their tyrosinase inhibitory activities were evaluated. Two of them showed significant tyrosinase inhibitory activities at 25 μmol·L^(-1).