3-[(E)-methoxyiminomethyl]phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-[(E)-methoxyiminomethyl]phenol
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: HDPBJRFWHXHXNF-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(E)-methoxyiminomethyl]phenol 、 (E)-2-(2-溴甲基苯基)-2-甲氧亚胺基乙酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以43%的产率得到methyl (2E)-2-methoxyimino-2-[2-[[3-[(E)-methoxyiminomethyl]phenoxy]methyl]phenyl]acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of kresoxim-methyl analogues as novel inhibitors of hypoxia-inducible factor (HIF)-1 accumulation in cancer cells

  摘要：

  We designed and synthesized strobilurin analogues as hypoxia-inducible factor (HIF) inhibitors based on the molecular structure of kresoxim-methyl. Biological evaluation in human colorectal cancer HCT116 cells showed that most of the synthesized kresoxim-methyl analogues possessed moderate to potent inhibitory activity against hypoxia-induced HIF-1 transcriptional activation. Three candidates, compounds 11b, 11c, and 11d were identified as potent inhibitors against HIF-1 activation with IC50 values of 0.60-0.94 mu M. Under hypoxic condition, compounds 11b, 11c, and 11d increased the intracellular oxygen contents, thereby attenuating the hypoxia-induced accumulation of HIF-1 alpha protein. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.05.024
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 间羟基苯甲醛 以 甲醇 为溶剂， 反应 12.0h， 生成 3-[(E)-methoxyiminomethyl]phenol
  参考文献：
  名称：

  Synthesis and biological evaluation of kresoxim-methyl analogues as novel inhibitors of hypoxia-inducible factor (HIF)-1 accumulation in cancer cells

  摘要：

  We designed and synthesized strobilurin analogues as hypoxia-inducible factor (HIF) inhibitors based on the molecular structure of kresoxim-methyl. Biological evaluation in human colorectal cancer HCT116 cells showed that most of the synthesized kresoxim-methyl analogues possessed moderate to potent inhibitory activity against hypoxia-induced HIF-1 transcriptional activation. Three candidates, compounds 11b, 11c, and 11d were identified as potent inhibitors against HIF-1 activation with IC50 values of 0.60-0.94 mu M. Under hypoxic condition, compounds 11b, 11c, and 11d increased the intracellular oxygen contents, thereby attenuating the hypoxia-induced accumulation of HIF-1 alpha protein. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.05.024

文献信息

• STETTER, J.;BUECHEL, K. H.;FROHBERGER, P. -E.;REINECKE, P.;BRANDES, W.
  作者：STETTER, J.、BUECHEL, K. H.、FROHBERGER, P. -E.、REINECKE, P.、BRANDES, W.

  DOI：——

  日期：——
• Synthesis and biological evaluation of kresoxim-methyl analogues as novel inhibitors of hypoxia-inducible factor (HIF)-1 accumulation in cancer cells
  作者：Sanghyuck Lee、Oh Seok Kwon、Chang-Soo Lee、Misun Won、Hyun Seung Ban、Choon Sup Ra

  DOI：10.1016/j.bmcl.2017.05.024

  日期：2017.7

  We designed and synthesized strobilurin analogues as hypoxia-inducible factor (HIF) inhibitors based on the molecular structure of kresoxim-methyl. Biological evaluation in human colorectal cancer HCT116 cells showed that most of the synthesized kresoxim-methyl analogues possessed moderate to potent inhibitory activity against hypoxia-induced HIF-1 transcriptional activation. Three candidates, compounds 11b, 11c, and 11d were identified as potent inhibitors against HIF-1 activation with IC50 values of 0.60-0.94 mu M. Under hypoxic condition, compounds 11b, 11c, and 11d increased the intracellular oxygen contents, thereby attenuating the hypoxia-induced accumulation of HIF-1 alpha protein. (C) 2017 Elsevier Ltd. All rights reserved.