(2S)-2-[(3aS,4R,7S,7aR)-1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl]-3-(1H-imidazol-5-yl)propanoic acid | 391647-87-3

• 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)-2-[(3aS,4R,7S,7aR)-1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl]-3-(1H-imidazol-5-yl)propanoic acid
• CAS: 391647-87-3
• 化学式: C₁₄H₁₅N₃O₅
• 分子量: 305.29
• InChiKey: OFGIVLPLQBBJEK-QUARPLMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-组氨酸 、 norcantharidin 以 乙醇 、 水 为溶剂， 反应 48.0h， 以97%的产率得到(2S)-2-[(3aS,4R,7S,7aR)-1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl]-3-(1H-imidazol-5-yl)propanoic acid
  参考文献：
  名称：

  Synthesis, Characterization and Crystal Structure of Optically Active L- and D-Histidine Norcantharimide

  摘要：

  L-组氨酸和D-组氨酸norcantharimide具有显著的PP2A抑制作用。它们是通过一种高效的组合方法合成的，在95%的EtOH溶液中，在低温条件下将诺坎特苷和L-组氨酸溶解，得到L-组氨酸诺坎特酰胺，收率为97%。L-histidine norcantharimide 通过 X 射线进行表征。该单晶体为正方晶，空间群为 P2(1)2(1)2(1)。a = b = g = 90°，Mr = 305.29，V = 1370.77(11) Å3，D = 1.479 Mg/m3，F(000) = 640，Z = 4。该晶体结构通过涉及 N-H 和 COO- 基团的分子间氢键网络得以稳定。

  DOI：

  10.14233/ajchem.2014.17750

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, Characterization and Crystal Structure of Optically Active L- and D-Histidine Norcantharimide
  作者：Dexiu Liu、Jie Sun、Yanfeng Wang

  DOI：10.14233/ajchem.2014.17750

  日期：——

  L- and D-histidine norcantharimide was showed significant PP2A inhibitors effect. They were synthesized through a highly efficient combinatorial approach , to a solution of norcantharidin and L-histidine in 95 % EtOH under temperature affords L-histidine norcantharimide in 97 % yield. L-histidine norcantharimide was characterized by X-ray. This single crystal was orthorhombic with the space group P2(1)2(1)2(1). One unit cell dimensions were a = 10.1553(4) Å, b = 10.4840(5) Å and c = 12.8749(6) Å, respectively. a = b = g = 90°, Mr = 305.29, V = 1370.77(11) Å3, D = 1.479 Mg/m3, F(000) = 640 and Z = 4. The crystal structure is stabilized by a network of intermolecular hydrogen bonds involving N-H and COO– group.

  L-组氨酸和D-组氨酸norcantharimide具有显著的PP2A抑制作用。它们是通过一种高效的组合方法合成的，在95%的EtOH溶液中，在低温条件下将诺坎特苷和L-组氨酸溶解，得到L-组氨酸诺坎特酰胺，收率为97%。L-histidine norcantharimide 通过 X 射线进行表征。该单晶体为正方晶，空间群为 P2(1)2(1)2(1)。a = b = g = 90°，Mr = 305.29，V = 1370.77(11) Å3，D = 1.479 Mg/m3，F(000) = 640，Z = 4。该晶体结构通过涉及 N-H 和 COO- 基团的分子间氢键网络得以稳定。