5-chloro-2-<2-<(2-hydroxyethyl)amino>ethyl>-7-<(2,4,6-trimethylphenyl)methoxy>anthra<1,9-cd>pyrazol-6(2H)-one | 109921-40-6

• 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-<(2,4,6-trimethylphenyl)methoxy>anthra<1,9-cd>pyrazol-6(2H)-one
• 英文别名: 5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7-[(2,4,6-trimethylphenyl)methoxy]anthra[1,9-cd]pyrazol-6(2H)-one；5-chloro-2-{2-[(2-hydroxyethyl)amino]ethyl}-7-[(2,4,6-trimethylphenyl)methoxy]anthra(1,9-cd)pyrazol-6(2H)-one；10-chloro-14-[2-(2-hydroxyethylamino)ethyl]-6-[(2,4,6-trimethylphenyl)methoxy]-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: 109921-40-6
• 化学式: C₂₈H₂₈ClN₃O₃
• 分子量: 490.002
• InChiKey: UQOGBPHRHFFBIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  179.5-183.5 °C
• 沸点：
  722.3±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.4
• 氢给体数：
  2
• 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-<(2,4,6-trimethylphenyl)methoxy>anthra<1,9-cd>pyrazol-6(2H)-one 在 盐酸 作用下， 以100%的产率得到5-chloro-2-<2-<(2-hydroxyethyl)amino>ethyl>-7-hydroxyanthra<1,9-cd>pyrazol-6(2H)-one hydrochloride
  参考文献：
  名称：

  Reversal of the regioselectivity of anthrapyrazole formation. A new synthesis of losoxantrone (DUP941)

  摘要：

  Losoxantrone, a potent anticancer agent, has been efficiently synthesized in a 6 step process from 5-hydroxy-1,4-dichloroanthracene-9,10-dione.

  DOI：

  10.1016/s0040-4039(00)73069-3
• 作为产物：
  描述：

  1,4-dichloro-5-<(2,4,6-trimethylphenyl)methoxy>-9,10-anthracenedione 在 吡啶 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 生成 5-chloro-2-<2-<(2-hydroxyethyl)amino>ethyl>-7-<(2,4,6-trimethylphenyl)methoxy>anthra<1,9-cd>pyrazol-6(2H)-one
  参考文献：
  名称：

  Reversal of the regioselectivity of anthrapyrazole formation. A new synthesis of losoxantrone (DUP941)

  摘要：

  Losoxantrone, a potent anticancer agent, has been efficiently synthesized in a 6 step process from 5-hydroxy-1,4-dichloroanthracene-9,10-dione.

  DOI：

  10.1016/s0040-4039(00)73069-3

文献信息

• Anticancer anthrapyrazoles. Improved syntheses of clinical agents CI-937, CI-941, and piroxantrone hydrochloride
  作者：Vladimir G. Beylin、Norman L. Colbry、Om P. Goel、Jerome E. Haky、Donald R. Johnson、Judith L. Johnson、Gerald D. Kanter、Robert L. Leeds、Boguslawa Leja、Edward P. Lewis、Christopher D. Rithner、H. D. Hollis Showalter、Anthony D. Sercel、William R. Turner、Susan E. Uhlendorf

  DOI：10.1002/jhet.5570260117

  日期：1989.1

  Improved processes for the synthesis of bulk quantities of the anthrapyrazole clinical agents CI-937, CI-941, and piroxantrone hydrochloride are reported. Reported also are detailed analytical and spectroscopic data for these agents and intermediates of the synthetic sequences.

  据报道，用于合成大量蒽吡咯临床药物CI-937，CI-941和盐酸吡咯酮的改进方法。还报告了这些试剂和合成序列中间体的详细分析和光谱数据。
• 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。
• BEYLIN, VLADIMIR G.;COLBRY, NORMAN L.;GOEL, OM P.;HAKY, JEROME E.;JOHNSON+, J. HETEROCYCL. CHEM., 26,(1989) N, C. 85-96
  作者：BEYLIN, VLADIMIR G.、COLBRY, NORMAN L.、GOEL, OM P.、HAKY, JEROME E.、JOHNSON+

  DOI：——

  日期：——
• Improved process for preparing substituted anthra[1,9-cd]-pyrazol-6(2H)-ones
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0244819B1

  公开（公告）日：1992-08-12
• INTERMEDIATES AND METHODS FOR THE SYNTHESIS OF ANTHRAPYRAZOLONE ANTICANCER AGENTS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0700390B1

  公开（公告）日：1998-11-18