3,4-dihydroxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide | 1186309-88-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 3,4-dihydroxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide
• 英文别名: houttuynamide A；N-protocatechuoyltyramine；becatamide；3,4-dihydroxy-N-(4-hydroxyphenethyl)benzamide
• CAS: 1186309-88-5
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: VGIFBSQQOUBLSS-UHFFFAOYSA-N

物化性质

• 熔点：
  218-221 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  548.4±50.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  原儿茶酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 3,4-dihydroxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide
  参考文献：
  名称：

  Protective effects of veskamide, enferamide, becatamide, and oretamide on H2O2-induced apoptosis of PC-12 cells

  摘要：

  Veskamide, enferamide, becatamide. and oretamide are phenolic amides whose analogues are found in plants. In this study, the four amides were prepared by chemical synthesis and their protective effects on H2O2-induced apoptosis in PC-12 cells were investigated. The syntheses were relatively simple and the yields were more than 43%. Using NMR spectroscopic methods, the chemical structures of veskamide, enferamide, becatamide, and oretamide were confirmed. The decreasing order of the protective effects on H2O2-induced apoptosis was becatamide > enferamide >= oretamide > veskamide. In fact, becatamide suppressed H2O2-induced mitochondrial membrane depolarization in a dose-dependent manner. At the concentration of 10 mu M, becatamide maintained mitochondrial membrane depolarization at 16% compared to 51% in H2O2-treated PC-12 cells (P < 0.05). Also, at the same concentration, becatamide inhibited H2O2-induced caspase-9 activation and caspase-independent chromatin condensation by 68% (P < 0.05) and 73% (P < 0.05), respectively. This is the first report about the chemical synthesis of becatamide and its potential biological activity to inhibit H2O2-induced apoptosis of PC-12 cells via protecting mitochondrial membrane integrity, thereby suppressing caspase-9 activation and chromatin condensation. Published by Elsevier GmbH.

  DOI：

  10.1016/j.phymed.2011.01.025

文献信息

• N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells
  作者：Yoshimitsu Yamazaki、Yasuhiro Kawano、Akiko Yamanaka、Susumu Maruyama

  DOI：10.1016/j.bmcl.2009.05.115

  日期：2009.8

  A series of N-acyl derivatives of tyramine, tryptamine, and serotonin were synthesized and tested on anti-melanogenic activity. The serotonin derivatives such as N-caffeoylserotonin (3) and N-protocatechuoylserotonin (9) were inhibitory to tyrosinase from mouse B16 and human HMV-II melanoma cells, while the corresponding derivatives of tryptamine and 5-methoxytryptamine were almost inactive or less active than the serotonin derivatives. The inhibitory activity of the serotonin derivatives increased with increasing number of phenolic hydroxyl groups in the acyl moiety. Melanin formation in the culture of B16 cells was suppressed by 3 and 9 with no cytotoxicity in the concentration range tested (IC50 = 15, 3 and 111 mu M for 3, 9, and kojic acid, respectively). Thus the N-acylserotonin derivatives having a dihydroxyphenyl group are potential anti-melanogenic agents. Their inhibition of tyrosinase is primarily performed through the 5-hydroxyindole moiety and further strengthened by the phenolic hydroxyl groups in the acyl moiety. (C) 2009 Elsevier Ltd. All rights reserved.
• Protective effects of veskamide, enferamide, becatamide, and oretamide on H2O2-induced apoptosis of PC-12 cells
  作者：Jae B. Park

  DOI：10.1016/j.phymed.2011.01.025

  日期：2011.7

  Veskamide, enferamide, becatamide. and oretamide are phenolic amides whose analogues are found in plants. In this study, the four amides were prepared by chemical synthesis and their protective effects on H2O2-induced apoptosis in PC-12 cells were investigated. The syntheses were relatively simple and the yields were more than 43%. Using NMR spectroscopic methods, the chemical structures of veskamide, enferamide, becatamide, and oretamide were confirmed. The decreasing order of the protective effects on H2O2-induced apoptosis was becatamide > enferamide >= oretamide > veskamide. In fact, becatamide suppressed H2O2-induced mitochondrial membrane depolarization in a dose-dependent manner. At the concentration of 10 mu M, becatamide maintained mitochondrial membrane depolarization at 16% compared to 51% in H2O2-treated PC-12 cells (P < 0.05). Also, at the same concentration, becatamide inhibited H2O2-induced caspase-9 activation and caspase-independent chromatin condensation by 68% (P < 0.05) and 73% (P < 0.05), respectively. This is the first report about the chemical synthesis of becatamide and its potential biological activity to inhibit H2O2-induced apoptosis of PC-12 cells via protecting mitochondrial membrane integrity, thereby suppressing caspase-9 activation and chromatin condensation. Published by Elsevier GmbH.