8,11-二[2-(2-羟基乙基氨基)乙基氨基]-6-甲氧基-1,2,3,4-四氢苯并[a]蒽-7,12-二酮 | 124511-81-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 中文名称: 8,11-二[2-(2-羟基乙基氨基)乙基氨基]-6-甲氧基-1,2,3,4-四氢苯并[a]蒽-7,12-二酮
• 中文别名: 3,3-二[4-(二甲氨基)苯基]-6-(1-吡咯烷基)苯酞
• 英文名称: 8,11-Bis((2-((2-hydroxyethyl)amino)ethyl)amino)-6-methoxy-1,2,3,4-tetrahydro-7,12-benz(a)anthraquinone
• 英文别名: 8,11-bis[2-(2-hydroxyethylamino)ethylamino]-6-methoxy-1,2,3,4-tetrahydrobenzo[a]anthracene-7,12-dione
• CAS: 124511-81-5
• 化学式: C₂₇H₃₆N₄O₅
• 分子量: 496.607
• InChiKey: WVHLYXXUTXVUMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  132
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8,11-二[2-(2-羟基乙基氨基)乙基氨基]-6-甲氧基-1,2,3,4-四氢苯并[a]蒽-7,12-二酮 在 盐酸 作用下， 以 异丙醇 为溶剂， 以161.3 mg的产率得到8,11-Bis-[2-(2-hydroxy-ethylamino)-ethylamino]-6-methoxy-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione; hydrochloride
  参考文献：
  名称：

  Antitumor properties of tetrahydrobenz(a)anthraquinone derivatives

  摘要：

  The compound 8,11-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]- 6-methoxy-1,2,3,4-tetrahydro-7,12-benz[a]-anthraquinone (7) was synthesized from 3,6-dimethoxyphthalic anhydride and 6-methoxy-1,2,3,4-tetrahydronaphthalene by a Friedel-Crafts reaction, cyclization to form a dihydroxyanthraquinone, and conversion into the amino-substituted derivative by reaction with 2-[(2-hydroxyethyl)amino]ethylamine. The new compound, a ring D analogue of mitoxantrone, showed growth inhibition, at micromolar concentrations, of murine leukemia 1210, human lung H125, human breast MCF7, human ovary 121, and human colon WiDr and increased the life span of leukemic mice by 38%.

  DOI：

  10.1021/jm00164a004
• 作为产物：
  描述：

  6,11-dimethoxy-8-hydroxy-1,2,3,4-tetrahydrobenzanthracene-7,12-dione 在 硫酸 、 氢溴酸 、 锌 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 44.0h， 生成 8,11-二[2-(2-羟基乙基氨基)乙基氨基]-6-甲氧基-1,2,3,4-四氢苯并[a]蒽-7,12-二酮
  参考文献：
  名称：

  Antitumor properties of tetrahydrobenz(a)anthraquinone derivatives

  摘要：

  The compound 8,11-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]- 6-methoxy-1,2,3,4-tetrahydro-7,12-benz[a]-anthraquinone (7) was synthesized from 3,6-dimethoxyphthalic anhydride and 6-methoxy-1,2,3,4-tetrahydronaphthalene by a Friedel-Crafts reaction, cyclization to form a dihydroxyanthraquinone, and conversion into the amino-substituted derivative by reaction with 2-[(2-hydroxyethyl)amino]ethylamine. The new compound, a ring D analogue of mitoxantrone, showed growth inhibition, at micromolar concentrations, of murine leukemia 1210, human lung H125, human breast MCF7, human ovary 121, and human colon WiDr and increased the life span of leukemic mice by 38%.

  DOI：

  10.1021/jm00164a004

文献信息

• Antitumor properties of tetrahydrobenz(a)anthraquinone derivatives
  作者：Charles E. Morreal、Ralph J. Bernacki、Marilyn Hillman、Alice Atwood、Donna Cartonia

  DOI：10.1021/jm00164a004

  日期：1990.2

  The compound 8,11-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]- 6-methoxy-1,2,3,4-tetrahydro-7,12-benz[a]-anthraquinone (7) was synthesized from 3,6-dimethoxyphthalic anhydride and 6-methoxy-1,2,3,4-tetrahydronaphthalene by a Friedel-Crafts reaction, cyclization to form a dihydroxyanthraquinone, and conversion into the amino-substituted derivative by reaction with 2-[(2-hydroxyethyl)amino]ethylamine. The new compound, a ring D analogue of mitoxantrone, showed growth inhibition, at micromolar concentrations, of murine leukemia 1210, human lung H125, human breast MCF7, human ovary 121, and human colon WiDr and increased the life span of leukemic mice by 38%.