2-(1,3-dioxooctahydro-2H-4,7-epoxyisoindol-2-yl)acetic acid | 1212310-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(1,3-dioxooctahydro-2H-4,7-epoxyisoindol-2-yl)acetic acid
• 英文别名: 2-{3,5-Dioxo-10-oxa-4-azatricyclo[5.2.1.0,2,6]decan-4-yl}acetic acid；2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl)acetic acid
• CAS: 1212310-79-6
• 化学式: C₁₀H₁₁NO₅
• mdl: MFCD04092777
• 分子量: 225.201
• InChiKey: JEHKXTYZFSUTKK-UHFFFAOYSA-N

物化性质

• 沸点：
  536.2±45.0 °C(Predicted)
• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-(1,3-dioxooctahydro-2H-4,7-epoxyisoindol-2-yl)acetic acid 、 (5S,8aR,9R)-5-amino-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one 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 二氯甲烷 为溶剂， 以68%的产率得到2-(1,3-dioxooctahydro-2H-4,7-epoxyisoindol-2-yl)-N-((5S,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)acetamide
  参考文献：
  名称：

  Conjugates of podophyllotoxin and norcantharidin as dual inhibitors of topoisomeraseⅡ and protein phosphatase 2A

  摘要：

  A series of novel conjugates of podophyllotoxin and norcantharidin was designed using association strategy, and synthesized by coupling 4'-demethylepipodophyllotoxin with N-amino acid norcantharimides, and their cytotoxicitiy was evaluated against four human tumor cell lines (A-549, HepG2, HeLa and HCT-8) and normal human diploid fibroblast line WI-38. These compounds exhibited potent cytotoxic effects on tumor cell lines, whereas it was less toxic to WI-38 cells than anticancer drug VP-16 or its parent compound norcantharidin. Furthermore, conjugates 7a, 7c, 7f, 7j, 7k and 7I displayed excellent PP2A inhibition activity with IC50 values of 0.49-9.52 mu M. The most potent compound 7I also exhibited topoisomerasellinhibition activity. In addition, compound 7I induced cell-cycle arrest in the G2/M phase in HepG2 by regulating levels of cyclinB1 and cdc2. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.031
• 作为产物：
  描述：

  聚甘氨酸 、 去甲斑蝥素 以76%的产率得到2-(1,3-dioxooctahydro-2H-4,7-epoxyisoindol-2-yl)acetic acid
  参考文献：
  名称：

  Conjugates of podophyllotoxin and norcantharidin as dual inhibitors of topoisomeraseⅡ and protein phosphatase 2A

  摘要：

  A series of novel conjugates of podophyllotoxin and norcantharidin was designed using association strategy, and synthesized by coupling 4'-demethylepipodophyllotoxin with N-amino acid norcantharimides, and their cytotoxicitiy was evaluated against four human tumor cell lines (A-549, HepG2, HeLa and HCT-8) and normal human diploid fibroblast line WI-38. These compounds exhibited potent cytotoxic effects on tumor cell lines, whereas it was less toxic to WI-38 cells than anticancer drug VP-16 or its parent compound norcantharidin. Furthermore, conjugates 7a, 7c, 7f, 7j, 7k and 7I displayed excellent PP2A inhibition activity with IC50 values of 0.49-9.52 mu M. The most potent compound 7I also exhibited topoisomerasellinhibition activity. In addition, compound 7I induced cell-cycle arrest in the G2/M phase in HepG2 by regulating levels of cyclinB1 and cdc2. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.031