(2S,3S)-2-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl]-3-methylpentanoic acid

• 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: (2S,3S)-2-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl]-3-methylpentanoic acid
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: YIFUOPDSCCLWFD-IMHINIOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diphenyl [(amino)(o-chlorophenyl)methyl]phosphonate 、 (2S,3S)-2-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl]-3-methylpentanoic acid 在 二苯基磷酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69.5%的产率得到
  参考文献：
  名称：

  SYNTHESIS OF PHOSPHONODIPEPTIDE DERIVATIVES OF EXO-7-OXABICYCLO [2.2.1] HEPTANE-2,3-DICARBOXYLIC ANHYDRIDE

  摘要：

  A series of phosphonodipeptide derivatives of norcantharidin (exo-7-oxabicyclo[2.2.1] heptane-2,3-dicarboxylic anhydride) were synthesized and their structures were confirmed by H-1 NMR, P-31 NMR, IR, MS and elemental analysis.

  DOI：

  10.1080/10426509908031616
• 作为产物：
  描述：

  L-异亮氨酸 、 norcantharidin 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以80.6%的产率得到(2S,3S)-2-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl]-3-methylpentanoic acid
  参考文献：
  名称：

  SYNTHESIS OF PHOSPHONODIPEPTIDE DERIVATIVES OF EXO-7-OXABICYCLO [2.2.1] HEPTANE-2,3-DICARBOXYLIC ANHYDRIDE

  摘要：

  A series of phosphonodipeptide derivatives of norcantharidin (exo-7-oxabicyclo[2.2.1] heptane-2,3-dicarboxylic anhydride) were synthesized and their structures were confirmed by H-1 NMR, P-31 NMR, IR, MS and elemental analysis.

  DOI：

  10.1080/10426509908031616

文献信息

• Cantharimides: A new class of modified cantharidin analogues inhibiting protein phosphatases 1 and 2A
  作者：Adam McCluskey、Cecilia Walkom、Michael C Bowyer、Stephen P Ackland、Emma Gardiner、Jennette A Sakoff

  DOI：10.1016/s0960-894x(01)00594-7

  日期：2001.11

  Cantharidin and its analogues have been of considerable interest as potent inhibitors of the serine/threonine protein phosphatases 1 and 2A (PP1 and PP2A). However, limited modifications to the parent compounds is tolerated. As part of an ongoing study we have developed a new series of cantharidin analogues, the cantharimides. Inhibition studies indicate that cantharimides possessing a D- or L-histidine, are more potent inhibitors of PP1 and PP2A (PP1 IC50 = 3.22 +/- 0.7 muM; PP2A IC50 = 0.81 +/- 0.1 muM and PP1 IC50 = 2.82 +/- 0.6 muM; PP2A IC50 = 1.35 +/- 0.3 muM, respectively) than norcantharidin (PP1 IC50 = 5.31 +/- 0.76 muM; PP2A IC50 = 2.9 +/- 1.04 muM) and essentially equipotent with cantharidin (PP1 IC50 = 3.6 +/- 0.42 muM; PP2A IC50 = 0.36 +/- 0.08 muM). Cantharimides with non-polar or acidic amino acid residues are only poor inhibitors of PP1 and PP2A. (C) 2001 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF PHOSPHONODIPEPTIDE DERIVATIVES OF EXO-7-OXABICYCLO [2.2.1] HEPTANE-2,3-DICARBOXYLIC ANHYDRIDE
  作者：Zheng Hong Zhou、Zhong Biao Zhang、Ru Yu Chen

  DOI：10.1080/10426509908031616

  日期：1999.9.1

  A series of phosphonodipeptide derivatives of norcantharidin (exo-7-oxabicyclo[2.2.1] heptane-2,3-dicarboxylic anhydride) were synthesized and their structures were confirmed by H-1 NMR, P-31 NMR, IR, MS and elemental analysis.