3,4,5-trihydroxy-N-octadecylbenzamide | 87667-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,4,5-trihydroxy-N-octadecylbenzamide
• CAS: 87667-26-3
• 化学式: C₂₅H₄₃NO₄
• 分子量: 421.621
• InChiKey: WJGBNRKBCQYGCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  N-octadecyl-3,4,5-tribenzyloxybenzamide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以96%的产率得到3,4,5-trihydroxy-N-octadecylbenzamide
  参考文献：
  名称：

  Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (−)-epigallocatechin gallate

  摘要：

  Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate and gallamide derivatives and evaluated their antiproliferative effects on human leukemia HL-60 cells. Dodecyl 3,4,5-trihydroxybenzoate (6c) showed the most potent activity, being more potent than EGCG. To clarify the molecular mechanism of the antiproliferative action, we investigated the effects of 6c on various factors. Compound 6c was found to induce apoptosis mediated by endoplasmic reticulum (ER)-stress-related caspase-12. Upregulation of gadd-153, an ER-stress marker protein, was also observed. These results indicate that 6c induced apoptosis via the ER-stress-related pathway. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.063