1-(4-Chloro-butyl)-4,11-dihydroxy-1H-naphtho[2,3-f]indole-5,10-dione | 744270-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(4-Chloro-butyl)-4,11-dihydroxy-1H-naphtho[2,3-f]indole-5,10-dione
• 英文别名: 1-(4-chlorobutyl)-4,11-dihydroxynaphtho[2,3-f]indole-5,10-dione
• CAS: 744270-08-4
• 化学式: C₂₀H₁₆ClNO₄
• 分子量: 369.804
• InChiKey: IQDDLMFVVHXOJF-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162 °C(Solv: heptane (142-82-5); toluene (108-88-3))
• 沸点：
  622.3±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.53
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(4-Chloro-butyl)-4,11-dihydroxy-1H-naphtho[2,3-f]indole-5,10-dione 在 氯化亚砜 作用下， 以 N-甲基吡咯烷酮 、 苯 为溶剂， 反应 0.5h， 生成 1-{4-[Bis-(2-chloro-ethyl)-amino]-butyl}-4,11-dihydroxy-1H-naphtho[2,3-f]indole-5,10-dione
  参考文献：
  名称：

  Synthesis of 1-(ω-aminoalkyl)naphthoindolediones with antiproliferative properties

  摘要：

  The preparation and cytotoxic properties of 4,11-dihydroxynaphtho[2,3-f]indole-5,10-dione derivatives carrying N-aminoalkyl substituents are described. The N-aminobutylnaphthoindolediones obtained were studied in National Cancer Institute Screening Program and demonstrated high antiproliferative activity against 60 human cancer cell lines. All N-(4-aminobutyl) derivatives have higher potency than adriamycin or mitoxantrone against adriamycin selected multidrug resistant breast cancer cell line NCI/ADR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.042
• 作为产物：
  描述：

  4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione 在 cerium(III) chloride 、 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.0h， 生成 1-(4-Chloro-butyl)-4,11-dihydroxy-1H-naphtho[2,3-f]indole-5,10-dione
  参考文献：
  名称：

  Synthesis of 1-(ω-aminoalkyl)naphthoindolediones with antiproliferative properties

  摘要：

  The preparation and cytotoxic properties of 4,11-dihydroxynaphtho[2,3-f]indole-5,10-dione derivatives carrying N-aminoalkyl substituents are described. The N-aminobutylnaphthoindolediones obtained were studied in National Cancer Institute Screening Program and demonstrated high antiproliferative activity against 60 human cancer cell lines. All N-(4-aminobutyl) derivatives have higher potency than adriamycin or mitoxantrone against adriamycin selected multidrug resistant breast cancer cell line NCI/ADR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.042