1-氧代-1,3-二氢异苯并呋喃-4-甲腈 | 90483-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 1-氧代-1,3-二氢异苯并呋喃-4-甲腈
• 英文名称: 3-cyano-phthalide
• 英文别名: 1-oxo-1,3-dihydro-isobenzofuran-4-carbonitrile；4-Cyanphthalid；1-Oxo-1,3-dihydroisobenzofuran-4-carbonitrile；1-oxo-3H-2-benzofuran-4-carbonitrile
• CAS: 90483-95-7
• 化学式: C₉H₅NO₂
• mdl: MFCD06412578
• 分子量: 159.144
• InChiKey: BFNMZJQMWPPBKE-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C
• 沸点：
  413.2±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-氧代-1,3-二氢异苯并呋喃-4-甲腈 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 108.0h， 生成 7-cyano-12H-5,11a-diazadibenzo[b,h]fluoren-11-one
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of 22-Hydroxyacuminatine

  摘要：

  A total synthesis of 22-hydroxyacuminatine, a cytotoxic alkaloid isolated from Camptotheca acuminata, is reported. The key step in the synthesis involves the reaction of 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline with a brominated phthalide to generate a substituted pentacyclic 12H-5,11a-diazadibenzo[b,h]fluoren-11-one intermediate. Despite its structural resemblance to camptothecin and luotonin A, a biological evaluation of 22-hydroxyacuminatine in a topoisomerase I-deficient cell line P388/CPT45 has confirmed that the observed cytotoxicity is not due to topoisomerase I inhibition, even though 22-hydroxyacuminatine has a hydroxyl group that can theoretically hydrogen bond to Asp533. This result is consistent with the hypothesis that pi-pi stacking is more important than hydrogen-bonding interactions in determining topoisomerase I inhibitor binding in the ternary cleavage complex.

  DOI：

  10.1021/jm051116e
• 作为产物：
  描述：

  2-甲基-3-溴苯甲酸甲酯 在 二氯氧化铬 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 1-氧代-1,3-二氢异苯并呋喃-4-甲腈
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of 22-Hydroxyacuminatine

  摘要：

  A total synthesis of 22-hydroxyacuminatine, a cytotoxic alkaloid isolated from Camptotheca acuminata, is reported. The key step in the synthesis involves the reaction of 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline with a brominated phthalide to generate a substituted pentacyclic 12H-5,11a-diazadibenzo[b,h]fluoren-11-one intermediate. Despite its structural resemblance to camptothecin and luotonin A, a biological evaluation of 22-hydroxyacuminatine in a topoisomerase I-deficient cell line P388/CPT45 has confirmed that the observed cytotoxicity is not due to topoisomerase I inhibition, even though 22-hydroxyacuminatine has a hydroxyl group that can theoretically hydrogen bond to Asp533. This result is consistent with the hypothesis that pi-pi stacking is more important than hydrogen-bonding interactions in determining topoisomerase I inhibitor binding in the ternary cleavage complex.

  DOI：

  10.1021/jm051116e

文献信息

• Total Synthesis and Biological Evaluation of 22-Hydroxyacuminatine
  作者：Xiangshu Xiao、Smitha Antony、Yves Pommier、Mark Cushman

  DOI：10.1021/jm051116e

  日期：2006.2.1

  A total synthesis of 22-hydroxyacuminatine, a cytotoxic alkaloid isolated from Camptotheca acuminata, is reported. The key step in the synthesis involves the reaction of 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline with a brominated phthalide to generate a substituted pentacyclic 12H-5,11a-diazadibenzo[b,h]fluoren-11-one intermediate. Despite its structural resemblance to camptothecin and luotonin A, a biological evaluation of 22-hydroxyacuminatine in a topoisomerase I-deficient cell line P388/CPT45 has confirmed that the observed cytotoxicity is not due to topoisomerase I inhibition, even though 22-hydroxyacuminatine has a hydroxyl group that can theoretically hydrogen bond to Asp533. This result is consistent with the hypothesis that pi-pi stacking is more important than hydrogen-bonding interactions in determining topoisomerase I inhibitor binding in the ternary cleavage complex.