3,4,5-trihydroxy-N'-(4-((3-methoxybenzyl)oxy)benzylidene)benzohydrazide

• 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'-(4-((3-methoxybenzyl)oxy)benzylidene)benzohydrazide
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: BEXDMMNZSLPJSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  120.61
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  没食子酸乙酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 42.0h， 生成 3,4,5-trihydroxy-N'-(4-((3-methoxybenzyl)oxy)benzylidene)benzohydrazide
  参考文献：
  名称：

  Development of hydroxy-based sphingosine kinase inhibitors and anti-inflammation in dextran sodium sulfate induced colitis in mice

  摘要：

  Sphingosine kinase (SphK)-catalyzed production of sphingosine-1-phosphate (S1P) regulates cell growth, survival and proliferation as well as inflammatory status in animals. In recent study we reported the N'-(3-(benzyloxy)benzylidene)-3,4,5-trihydroxybenzohydrazide scaffold as a potent SphK inhibitor. As a continuation of these efforts, 51 derivatives were synthesized and evaluated by SphK1/2 inhibitory activities for structure-activity relationship (SAR) study. Among them, 33 was identified as the most potent SphK inhibitor. Potency of 33 was also observed to efficiently decrease SphK1/2 expression in human colorectal cancer cells (HCT116) and significantly inhibit dextran sodium sulfate (DSS)-induced colitis as well as the decreased expression of interleukin (IL)-6 and cyclooxygenase-2 (COX-2) in mouse models. Collectively, 33 was validated as an effective SphK inhibitor, which can be served as anti-inflammatory agent to probably treat inflammatory bowel diseases in human. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.047

文献信息

• Development of hydroxy-based sphingosine kinase inhibitors and anti-inflammation in dextran sodium sulfate induced colitis in mice
  作者：Meiyang Xi、Jun Ge、Xiaojian Wang、Chenbin Sun、Tianqi Liu、Liang Fang、Qiong Xiao、Dali Yin

  DOI：10.1016/j.bmc.2016.05.047

  日期：2016.7

  Sphingosine kinase (SphK)-catalyzed production of sphingosine-1-phosphate (S1P) regulates cell growth, survival and proliferation as well as inflammatory status in animals. In recent study we reported the N'-(3-(benzyloxy)benzylidene)-3,4,5-trihydroxybenzohydrazide scaffold as a potent SphK inhibitor. As a continuation of these efforts, 51 derivatives were synthesized and evaluated by SphK1/2 inhibitory activities for structure-activity relationship (SAR) study. Among them, 33 was identified as the most potent SphK inhibitor. Potency of 33 was also observed to efficiently decrease SphK1/2 expression in human colorectal cancer cells (HCT116) and significantly inhibit dextran sodium sulfate (DSS)-induced colitis as well as the decreased expression of interleukin (IL)-6 and cyclooxygenase-2 (COX-2) in mouse models. Collectively, 33 was validated as an effective SphK inhibitor, which can be served as anti-inflammatory agent to probably treat inflammatory bowel diseases in human. (C) 2016 Elsevier Ltd. All rights reserved.