以新药设计原理中的拼合原理为指导,将对苯二酚一侧酚羟基与具有生物活性的氨基酸进行偶联,以期得到活性更好、毒性更低的对苯二酚氨基酸缀合物.将对苯二酚的一侧酚羟基进行保护得到对苄氧基苯酚,将氨基被保护的氨基酸与其酚羟基进行偶联,去掉保护基后得到8种对苯二酚的氨基酸缀合物.在对苄氧基苯酚的酚羟基上引入乙酸连接片段,与氨基酸甲酯盐酸盐进行偶联,去掉保护基后得到8种对苯二酚的氨基酸缀合物.通过IR、1 H NMR、13C NMR和ESI-MS等技术手段对所合成的16种氨基酸缀合物进行了结构表征.对目标产物进行了美白活性研究.结果表明,化合物HQ-3b、HQ-3c、HQ-4a、HQ-4b、HQ-7c和HQ-8a对酪氨酸酶的抑制作用优于阳性对照物α-熊果苷(IC.=3.60),其中HQ-4b的IC50值低至0.15,有望成为新型化妆品美白剂.
参考文献
| [1] | Maeda K;Fukuda M.In Vitro Effectiveness of Several Whitening Cosmetic Components in Human Melanocytes[J].Journal of the Society of Cosmetic Chemists,199142(2):361-368. |
| [2] | Grimes P E.Melasma.Etiologic and Therapeutic Considerations[J].ARCHIVES OF DERMATOLOGY,1995131(12):1453-1457. |
| [3] | 邓菊香;王祖元.苯丙氨酸的生产现状与发展前景[J].安徽化工,2007(4):1-3. |
| [4] | Edelson J;Skinner C G;Ravel J M.Structural Specificity of Some Amino Acid Antagonists[J].Journal of the American Chemical Society,195981(19):5150-5153. |
| [5] | 董绪兵;毕焕改;刘业霞;于军辉;艾希珍.黄瓜幼苗干旱-低温交叉适应与渗透调节的关系[J].中国农业科学,2011(2):335-340. |
| [6] | 梁太波;张景玲;田雷;王建伟;尹启生;蔡宪杰;刘阳;张仕祥.干旱胁迫下外源甜菜碱和脯氨酸对烤烟抗氧化代谢的影响[J].烟草科技,2013(2):68-71. |
| [7] | Nakajima M;Shinoda I;Fukuwatari Y.Arbutin Increases the Pigmentation of Cultured Human Melanocytes Through Mechanisms Other Than the Induction of Tyrosinase Activity[J].PIGMENT CELL RESEARCH,199811(1):12-17. |
| [8] | Chakraborty A K;Funasaka Y;Komoto M.Effect of Arbutin on Melanogenic Proteins in Human Melanocytes[J].PIGMENT CELL RESEARCH,199811(4):206-212. |
| [9] | Maeda K;Fukuda M.Arbutin:Mechanism of Its Depigmenting Action in Human Melanocyte Culture[J].Journal of Pharmacology and Experimental Therapeutics,1996276(2):765-769. |
| [10] | Jimenez-Cervantes C;Solano F;Kobayashi T.A New Enzymatic Function in the Melanogenic Pathway:The 5,6-Dihydroxyindole-2-carboxylic Acid Oxidase Activity of Tyrosinase-Related Protein-1 (TRP1)[J].Journal of Biological Chemistry,1994269(27):17993-18000. |
| [11] | 张文征;戴立言;王晓钟;陈英奇.4-[（2-四氢吡喃）氧]苯酚的合成[J].高校化学工程学报,2010(1):117-121. |
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