4-[(3-ethoxycarbonyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)amino]-4-oxobut-2-enoic acid | 380158-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七噻吩
• 英文名称: 4-[(3-ethoxycarbonyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)amino]-4-oxobut-2-enoic acid
• CAS: 380158-17-8
• 化学式: C₁₆H₁₉NO₅S
• 分子量: 337.397
• InChiKey: QYPHUICUJZHSLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(3-ethoxycarbonyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)amino]-4-oxobut-2-enoic acid 、 硫脲 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 ethyl 2-{[(2-imino-4-oxo-1,3-thiazolidin-5-yl)acetyl]amino}-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
  参考文献：
  名称：

  Identification of iminooxothiazolidines as secreted frizzled related protein-1 inhibitors

  摘要：

  Secreted frizzled related protein-1 (sFRP-1) inhibitors have the potential to be used for the treatment of osteoporosis or other bone related disorders, since the level of sFRP-1 affects osteoblast apoptosis and proliferation. From high throughput screening, we have identified a class of iminooxothiazolidines as sFRP-1 inhibitors. Structure-activity relationships were established for various regions of the scaffold along with the biochemical characterization of this class to probe selectivity, binding and ex vivo activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.085
• 作为产物：
  描述：

  马来酸酐 、 2-氨基环庚烷并[B]噻吩-3-羧酸乙酯 以 乙醚 为溶剂， 反应 10.0h， 生成 4-[(3-ethoxycarbonyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)amino]-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Identification of iminooxothiazolidines as secreted frizzled related protein-1 inhibitors

  摘要：

  Secreted frizzled related protein-1 (sFRP-1) inhibitors have the potential to be used for the treatment of osteoporosis or other bone related disorders, since the level of sFRP-1 affects osteoblast apoptosis and proliferation. From high throughput screening, we have identified a class of iminooxothiazolidines as sFRP-1 inhibitors. Structure-activity relationships were established for various regions of the scaffold along with the biochemical characterization of this class to probe selectivity, binding and ex vivo activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.085