6-Chloro-3-nitro-2-(4-prop-2-enoxyanilino)benzoic acid | 144346-81-6

• 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: 6-Chloro-3-nitro-2-(4-prop-2-enoxyanilino)benzoic acid
• CAS: 144346-81-6
• 化学式: C₁₆H₁₃ClN₂O₅
• 分子量: 348.743
• InChiKey: MJHRXFRDUVJQSW-UHFFFAOYSA-N

物化性质

• 沸点：
  486.9±45.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Chloro-3-nitro-2-(4-prop-2-enoxyanilino)benzoic acid 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以48%的产率得到1-chloro-4-nitro-7-prop-2-enoxy-10H-acridin-9-one
  参考文献：
  名称：

  2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines, a new class of anticancer agents

  摘要：

  2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines were prepared from substituted anilines via the 1-chloro-4-nitroacridones followed by condensation with [(alkylamino)alkyl]hydrazines. Impressive activity was demonstrated for the 9-hydroxy, 9-alkoxy, and 9-acyloxy analogs in vitro on a L1210 leukemia line and in vivo against the P388 leukemia. Advanced studies led to the selection of 3bbb for clinical trial.

  DOI：

  10.1021/jm00104a001
• 作为产物：
  描述：

  2,6-二氯-3-硝基苯甲酸 、 4-(烯丙氧基)苯胺 在 N,N-二甲基苯胺 、 N,N-二异丙基乙胺 作用下， 反应 1.7h， 以49%的产率得到6-Chloro-3-nitro-2-(4-prop-2-enoxyanilino)benzoic acid
  参考文献：
  名称：

  2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines, a new class of anticancer agents

  摘要：

  2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines were prepared from substituted anilines via the 1-chloro-4-nitroacridones followed by condensation with [(alkylamino)alkyl]hydrazines. Impressive activity was demonstrated for the 9-hydroxy, 9-alkoxy, and 9-acyloxy analogs in vitro on a L1210 leukemia line and in vivo against the P388 leukemia. Advanced studies led to the selection of 3bbb for clinical trial.

  DOI：

  10.1021/jm00104a001

文献信息

• Capps David B., Dundar James, Kesten Suzanne R., Shillis Joan, Werbel Les+, J. Med. Chem., 35 (1992) N 26, S 4770-4778
  作者：Capps David B., Dundar James, Kesten Suzanne R., Shillis Joan, Werbel Les+

  DOI：——

  日期：——
• 2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines, a new class of anticancer agents
  作者：David B. Capps、James Dunbar、Suzanne R. Kesten、Joan Shillis、Leslie M. Werbel、Jacqueline Plowman、Donald L. Ward

  DOI：10.1021/jm00104a001

  日期：1992.12

  2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines were prepared from substituted anilines via the 1-chloro-4-nitroacridones followed by condensation with [(alkylamino)alkyl]hydrazines. Impressive activity was demonstrated for the 9-hydroxy, 9-alkoxy, and 9-acyloxy analogs in vitro on a L1210 leukemia line and in vivo against the P388 leukemia. Advanced studies led to the selection of 3bbb for clinical trial.