7-cyano-12H-5,11a-diazadibenzo[b,h]fluoren-11-one | 879627-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 7-cyano-12H-5,11a-diazadibenzo[b,h]fluoren-11-one
• 英文别名: 14-Oxo-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15,17,19-nonaene-19-carbonitrile
• CAS: 879627-91-5
• 化学式: C₂₀H₁₁N₃O
• 分子量: 309.327
• InChiKey: RXMLBQGWBMDMNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-cyano-12H-5,11a-diazadibenzo[b,h]fluoren-11-one 在 二异丁基氢化铝 、 草酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 以76%的产率得到14-Oxo-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15,17,19-nonaene-19-carbaldehyde
  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：

  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

文献信息

• Short and Efficient Total Synthesis of Luotonin A and 22-Hydroxyacuminatine Using A Common Cascade Strategy
  作者：Hai-Bin Zhou、Guan-Sai Liu、Zhu-Jun Yao

  DOI：10.1021/jo070837d

  日期：2007.8.1

  achieved in direct fashion and high overall yields (16% in eight steps and 47% in five steps, respectively). A mild cascade methodology was successfully applied in both syntheses as a common strategy. The new approach presents the advantages of short routes, high overall yields, use of stable intermediates, and ease of operations.

  以直接的方式和高的总收率（分别在8个步骤中为16％，在5个步骤中为47％）实现了22-羟基氨基丁酸和褪黑素A的总合成。温和的级联方法已成功应用于两种合成中，作为一种常见策略。这种新方法的优点是路线短，总收率高，使用稳定的中间体和易于操作。