4'-(7-oxabicyclo[2.2.1]-5-heptane-2,3-dicarboximide)benzoic acid | 6624-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-(7-oxabicyclo[2.2.1]-5-heptane-2,3-dicarboximide)benzoic acid
• 英文别名: 4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindol-2-yl)benzoic acid
• CAS: 6624-09-5
• 化学式: C₁₅H₁₃NO₅
• 分子量: 287.272
• InChiKey: MRGAEXCMDNFHJM-UHFFFAOYSA-N

物化性质

• 沸点：
  627.4±50.0 °C(Predicted)
• 密度：
  1.501±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4'-(7-oxabicyclo[2.2.1]-5-heptane-2,3-dicarboximide)benzoic acid 、 二正丁基氧化锡 以 甲苯 为溶剂， 以57.8%的产率得到
  参考文献：
  名称：

  苯甲酸二正丁锡4'-（7-氧杂双环[2,2,1] -5-庚烷-2,3-二苯甲酰亚胺）的合成，晶体结构和体外抗肿瘤活性

  摘要：

  氧化二丁基锡（IV）与邻苯二酚类似物4'-（7-氧杂双环[2,2,1] -5-庚烷-2,3-二羧酸二亚胺）苯甲酸A反应生成配合物[（p -C已经表征的8 H 8 NO 3 -C 6 H 4 -COOBu 2 Sn）2 O] 2（1）和（p -C 8 H 8 NO 3 -C 6 H 4 -COO）2 SnBu 2（2）通过IR和1 H，13 C，119 Sn NMR。已经确定了与大多数其他[（RCOOBu 2 Sn）2 O] 2类似的化合物（1）的单X射线晶体结构分析。二聚体的特征在于Bu 4 Sn 2 O 2单元的中心，两个Bu 2 Sn基团通过桥接氧原子连接。每个锡原子通过来自二丁基部分的两个碳和来自邻苯二酚衍生物的三个氧原子并桥接氧原子采用扭曲的三角双锥体结构。体外测试显示，化合物1和2对P388和HL-60具有高细胞毒性。

  DOI：

  10.1016/j.jorganchem.2005.01.062
• 作为产物：
  描述：

  去甲斑蝥素 、 对氨基苯甲酸 以66%的产率得到4'-(7-oxabicyclo[2.2.1]-5-heptane-2,3-dicarboximide)benzoic 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

文献信息

• Conjugates of podophyllotoxin and norcantharidin as dual inhibitors of topoisomeraseⅡ and protein phosphatase 2A
  作者：Zhen-Bo Tang、Yao-Zhang Chen、Jie Zhao、Xiao-Wen Guan、Yong-Xin Bo、Shi-Wu Chen、Ling Hui

  DOI：10.1016/j.ejmech.2016.07.031

  日期：2016.11

  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.
• Synthesis, crystal structure and in vitro antitumor activity of di-n-butyltin 4′-(7-oxabicyclo [2,2,1]-5-heptane-2,3-dicarboximide) benzoates
  作者：Yizong Zhou、Tao Jiang、Sumei Ren、Jingsheng Yu、Zhicheng Xia

  DOI：10.1016/j.jorganchem.2005.01.062

  日期：2005.4

  Dibutyltin(IV) oxide reacts with the cantharidin analogue, 4′-(7-oxabicyclo [2,2,1]-5-heptane-2,3-dicarboximide) benzoic acid, A, to give the complexes [(p-C8H8NO3–C6H4–COOBu2Sn)2O]2 (1) and (p-C8H8NO3–C6H4–COO)2SnBu2 (2) which had been characterized by IR and 1H, 13C, 119Sn NMR. Single X-ray crystal structure analysis has been determined for compound (1), which was analogue to most other [(RCOOBu2Sn)2O]2

  氧化二丁基锡（IV）与邻苯二酚类似物4'-（7-氧杂双环[2,2,1] -5-庚烷-2,3-二羧酸二亚胺）苯甲酸A反应生成配合物[（p -C已经表征的8 H 8 NO 3 -C 6 H 4 -COOBu 2 Sn）2 O] 2（1）和（p -C 8 H 8 NO 3 -C 6 H 4 -COO）2 SnBu 2（2）通过IR和1 H，13 C，119 Sn NMR。已经确定了与大多数其他[（RCOOBu 2 Sn）2 O] 2类似的化合物（1）的单X射线晶体结构分析。二聚体的特征在于Bu 4 Sn 2 O 2单元的中心，两个Bu 2 Sn基团通过桥接氧原子连接。每个锡原子通过来自二丁基部分的两个碳和来自邻苯二酚衍生物的三个氧原子并桥接氧原子采用扭曲的三角双锥体结构。体外测试显示，化合物1和2对P388和HL-60具有高细胞毒性。