5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7-hydroxyanthra[1,9-cd]pyrazol-6(2H)-one | 109921-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7-hydroxyanthra[1,9-cd]pyrazol-6(2H)-one
• 英文别名: 10-Chloro-6-hydroxy-14-[2-(2-hydroxyethylamino)ethyl]-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-8-one
• CAS: 109921-43-9
• 化学式: C₁₈H₁₆ClN₃O₃
• 分子量: 357.796
• InChiKey: NUYJKMWOLOWFNU-UHFFFAOYSA-N

物化性质

• 沸点：
  657.5±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7-hydroxyanthra[1,9-cd]pyrazol-6(2H)-one 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 1,1-dimethyl ethyl[2-[5-[(2-aminoethyl)amino]-7-hydroxy-6-oxoanthra[1,9-cd] pyrazol-2(6H)-yl]ethyl](2-hydroxyethyl)carbamate
  参考文献：
  名称：

  Synthesis of Losoxantrone Metabolites Isolated from Human Urine

  摘要：

  The first regiospecific synthesis of the monoacid metabolites (2) and (3) of losoxantrone is reported. In addition, synthesis of the diacid metabolite (4) via two different routes is also described. The chemical structures of these metabolites as well as their intermediates have been fully characterized.

  DOI：

  10.3987/com-99-8641

文献信息

• Process for preparing substituted anthra[1,9-cd]pyrazol-6(2H)-ones
  申请人：Warner-Lambert Company

  公开号：US04672129A1

  公开（公告）日：1987-06-09

  An improved process for producing anthra[1,9-cd]-pyrazol-6(2H)-ones from 1,4-dichloro-5,8-disubstituted 9,10-anthracenediones. The process produces higher yields by using a new combination of protecting groups on the compounds which allows for easier and cleaner chromatographic resolution. The compounds produced have antibacterial, antifungal, antileukemic, and antitumor activity.

  一种从1,4-二氯-5,8-二取代9,10-蒽酮中生产蒽[1,9-cd]-吡唑-6(2H)-酮的改进工艺。该工艺通过在化合物上使用新的保护基组合，使色谱分离更加容易和清洁，从而产生更高的产量。所生产的化合物具有抗菌、抗真菌、抗白血病和抗肿瘤活性。
• Improved process for preparing substituted anthra[1,9-cd]-pyrazol-6(2H)-ones
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0244819A2

  公开（公告）日：1987-11-11

  An improved process for producing anthra[1,9-cd]­pyrazol-6(2H)-ones from 1,4-dichloro-5,8-disubstituted 9,10-anthracenediones. The process produces higher yields by using a new combination of protecting groups on the compounds which allows for easier and cleaner chromatographic resolution. The compounds produced have antibacterial, antifungal, antileukemic, and antitumor activity.

  一种从 1,4-二氯-5,8-二取代 9,10-蒽二酮生产蒽并[1,9-cd]吡唑-6(2H)-酮的改进工艺。该工艺在化合物上使用了新的保护基团组合，使色谱解析更简单、更干净，从而提高了产量。生产出的化合物具有抗菌、抗真菌、抗白血病和抗肿瘤活性。
• US4672129A
  申请人：——

  公开号：US4672129A

  公开（公告）日：1987-06-09
• Synthesis of Losoxantrone Metabolites Isolated from Human Urine
  作者：Jung-Hui Sun、Jiasheng Yan、Zelleka Getahun、Michael A. Vavala、Gregory A. Nemeth

  DOI：10.3987/com-99-8641

  日期：——

  The first regiospecific synthesis of the monoacid metabolites (2) and (3) of losoxantrone is reported. In addition, synthesis of the diacid metabolite (4) via two different routes is also described. The chemical structures of these metabolites as well as their intermediates have been fully characterized.