11-Amino-5-(2-dimethylamino-ethyl)-5-aza-benzo[de]anthracene-4,6-dione | 294919-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 11-Amino-5-(2-dimethylamino-ethyl)-5-aza-benzo[de]anthracene-4,6-dione
• 英文别名: 3-Amino-11-[2-(dimethylamino)ethyl]-11-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,3,5,7,9(17),13,15-heptaene-10,12-dione
• CAS: 294919-86-1
• 化学式: C₂₀H₁₉N₃O₂
• 分子量: 333.39
• InChiKey: LMKAMKHUAUTREH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-Amino-5-(2-dimethylamino-ethyl)-5-aza-benzo[de]anthracene-4,6-dione 在 盐酸 、 sodium nitrite 作用下， 以22%的产率得到11-Chloro-5-(2-dimethylamino-ethyl)-5-aza-benzo[de]anthracene-4,6-dione
  参考文献：
  名称：

  Analogues of Amonafide and Azonafide with Novel Ring Systems

  摘要：

  Three new types of amonafide and azonafide analogues were synthesized and screened in a panel of human solid tumor cells and murine L1210 leukemia cells. The structural types included tetrahydroazonafides, which have the naphthalene chromophore of amonafide within the anthracene nucleus of azonafide; phenanthrene analogues, in which the linear anthracene nucleus is replaced by the bent phenanthrene nucleus; and azaphenanthrenes. The tetrahydroazonafides were generally intermediate in potencies between amonafide and azonafide against the tumor cells, but some of them had high potencies against the L1210 cells and were more potent against the MDR strain than the sensitive strain. The phenanthrene and azaphenanthrene analogues showed no improvement on the potencies of the anthracenes.

  DOI：

  10.1021/jm9905817
• 作为产物：
  描述：

  phenanthrene-8,9-dicarboxylic acid anhydride 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， -10.0~16.0 ℃ 、275.79 kPa 条件下， 反应 4.25h， 生成 11-Amino-5-(2-dimethylamino-ethyl)-5-aza-benzo[de]anthracene-4,6-dione
  参考文献：
  名称：

  Analogues of Amonafide and Azonafide with Novel Ring Systems

  摘要：

  Three new types of amonafide and azonafide analogues were synthesized and screened in a panel of human solid tumor cells and murine L1210 leukemia cells. The structural types included tetrahydroazonafides, which have the naphthalene chromophore of amonafide within the anthracene nucleus of azonafide; phenanthrene analogues, in which the linear anthracene nucleus is replaced by the bent phenanthrene nucleus; and azaphenanthrenes. The tetrahydroazonafides were generally intermediate in potencies between amonafide and azonafide against the tumor cells, but some of them had high potencies against the L1210 cells and were more potent against the MDR strain than the sensitive strain. The phenanthrene and azaphenanthrene analogues showed no improvement on the potencies of the anthracenes.

  DOI：

  10.1021/jm9905817

文献信息

• COMPOSITIONS AND METHODS TO IMPROVE THE THERAPEUTIC BENEFIT OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS INCLUDING SUBSTITUTED NAPHTHALIMIDES SUCH AS AMONAFIDE FOR THE TREATMENT OF IMMUNOLOGICAL, METABOLIC, INFECTIOUS, AND BENIGN OR NEOPLASTIC HYPERPROLIFERATIVE DISEASE CONDITIONS
  申请人：BROWN Dennis M.

  公开号：US20160067241A1

  公开（公告）日：2016-03-10

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to naphthalimides such as amonafide or analogs, derivatives, or prodrugs thereof.
• Analogues of Amonafide and Azonafide with Novel Ring Systems
  作者：Salah M. Sami、Robert T. Dorr、David S. Alberts、Anikó M. Sólyom、William A. Remers

  DOI：10.1021/jm9905817

  日期：2000.8.1

  Three new types of amonafide and azonafide analogues were synthesized and screened in a panel of human solid tumor cells and murine L1210 leukemia cells. The structural types included tetrahydroazonafides, which have the naphthalene chromophore of amonafide within the anthracene nucleus of azonafide; phenanthrene analogues, in which the linear anthracene nucleus is replaced by the bent phenanthrene nucleus; and azaphenanthrenes. The tetrahydroazonafides were generally intermediate in potencies between amonafide and azonafide against the tumor cells, but some of them had high potencies against the L1210 cells and were more potent against the MDR strain than the sensitive strain. The phenanthrene and azaphenanthrene analogues showed no improvement on the potencies of the anthracenes.