methyl (2S)-1-[[5-[(E)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]furan-2-yl]methyl]piperidine-2-carboxylate | 1415650-34-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-1-[[5-[(E)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]furan-2-yl]methyl]piperidine-2-carboxylate
• CAS: 1415650-34-8
• 化学式: C₂₁H₂₁FN₂O₄
• 分子量: 384.407
• InChiKey: HXPWJWOPMQAGGM-OXRZLYTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-[[5-[(E)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]furan-2-yl]methyl]piperidine-2-carboxylate 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 methyl (2S)-1-[[5-[(E)-[5-fluoro-2-oxo-1-[[5-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]furan-2-yl]methyl]indol-3-ylidene]methyl]furan-2-yl]methyl]piperidine-2-carboxylate
  参考文献：
  名称：

  Discovery of di-indolinone as a novel scaffold for protein tyrosine phosphatase 1B inhibitors

  摘要：

  A series of di-indolinone derivatives was designed and synthesized to optimize our lead compounds basing on molecular docking study as PTP1B inhibitors. Successive enzymatic assay identified the synthetic di-indolinone as novel PTP1B inhibitors with low micromole-ranged inhibitory activity and at least several-fold selectivity over other tested homologous PTPs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.054
• 作为产物：
  描述：

  5-氟吲哚-2-酮 、 (S)-methyl 1-((5-formylfuran-2-yl)methyl)piperidine-2-carboxylate 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以66%的产率得到methyl (2S)-1-[[5-[(E)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]furan-2-yl]methyl]piperidine-2-carboxylate
  参考文献：
  名称：

  Discovery of di-indolinone as a novel scaffold for protein tyrosine phosphatase 1B inhibitors

  摘要：

  A series of di-indolinone derivatives was designed and synthesized to optimize our lead compounds basing on molecular docking study as PTP1B inhibitors. Successive enzymatic assay identified the synthetic di-indolinone as novel PTP1B inhibitors with low micromole-ranged inhibitory activity and at least several-fold selectivity over other tested homologous PTPs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.054

文献信息

• Discovery of di-indolinone as a novel scaffold for protein tyrosine phosphatase 1B inhibitors
  作者：Hou-ling Dai、Li-xin Gao、Ying Yang、Jing-ya Li、Jia-gao Cheng、Jia Li、Ren Wen、Yan-qing Peng、Jian-bin Zheng

  DOI：10.1016/j.bmcl.2012.10.054

  日期：2012.12

  A series of di-indolinone derivatives was designed and synthesized to optimize our lead compounds basing on molecular docking study as PTP1B inhibitors. Successive enzymatic assay identified the synthetic di-indolinone as novel PTP1B inhibitors with low micromole-ranged inhibitory activity and at least several-fold selectivity over other tested homologous PTPs. (C) 2012 Elsevier Ltd. All rights reserved.