cis-5-morpholinotetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione | 1221289-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: cis-5-morpholinotetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione
• 英文别名: (3aS,6aR)-5-morpholin-4-yl-1,3,3a,6a-tetrahydrofuro[3,4-c]pyrrole-4,6-dione
• CAS: 1221289-25-3
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: IAWRYWKNXWMHRR-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氨基吗啉 、 (3a,6a-cis)-tetrahydrofuro[3,4-c]furan-1,3-dione 以 甲苯 为溶剂， 反应 0.23h， 以77%的产率得到cis-5-morpholinotetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge

  摘要：

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.004

文献信息

• Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
  作者：Ali Thaqi、Janet L. Scott、Jayne Gilbert、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.ejmech.2010.01.004

  日期：2010.5

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.