| 1310012-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• CAS: 1310012-70-4
• 化学式: C₄₇H₆₁N₇O₄
• 分子量: 788.046
• InChiKey: IWEYOEZQEFRZKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  58.0
• 可旋转键数：
  25.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  161.67
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 Tris-amine resin 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Improved synthesis of 15-deoxyspergualin analogs using the Ugi multi-component reaction

  摘要：

  Spergualin is a natural product that exhibits immunosuppressive, anti-tumor and anti-bacterial activities. Its derivatives, such as 15-deoxyspergualin (15-DSG), have been clinically approved for acute allograft rejection. However, the reported syntheses are cumbersome (>10 steps) and they suffer from low overall yields (similar to 0.3% to 18%). Moreover, spergualin and its derivatives are chemically unstable and rapidly hydrolyzed in aqueous buffer. Here, we have re-explored these issues and report a modified synthetic route with significantly improved overall yield (similar to 31% to 47%). The key transformation is a microwave-accelerated Ugi multi-component reaction that is used to generate the peptoid core in a single step. Using the products of this route, we found that modifications of the hemiaminal significantly increased chemical stability. Thus, we anticipate that this synthetic route will improve access to biologically active 15-DSG derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.079
• 作为产物：
  描述：

  7-[({[(Tert-butoxy)carbonyl]amino}({[(tert-butoxy)carbonyl]imino})methyl)amino]heptanoicacid 在 磷酸 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.83h， 生成
  参考文献：
  名称：

  Improved synthesis of 15-deoxyspergualin analogs using the Ugi multi-component reaction

  摘要：

  Spergualin is a natural product that exhibits immunosuppressive, anti-tumor and anti-bacterial activities. Its derivatives, such as 15-deoxyspergualin (15-DSG), have been clinically approved for acute allograft rejection. However, the reported syntheses are cumbersome (>10 steps) and they suffer from low overall yields (similar to 0.3% to 18%). Moreover, spergualin and its derivatives are chemically unstable and rapidly hydrolyzed in aqueous buffer. Here, we have re-explored these issues and report a modified synthetic route with significantly improved overall yield (similar to 31% to 47%). The key transformation is a microwave-accelerated Ugi multi-component reaction that is used to generate the peptoid core in a single step. Using the products of this route, we found that modifications of the hemiaminal significantly increased chemical stability. Thus, we anticipate that this synthetic route will improve access to biologically active 15-DSG derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.079