2-amino-7-benzylamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid bis-diethylamide | 64377-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-amino-7-benzylamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid bis-diethylamide
• 英文别名: 2-amino-7-(benzylamino)-1-N,1-N,9-N,9-N-tetraethyl-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboxamide
• CAS: 64377-53-3
• 化学式: C₃₁H₃₇N₅O₄
• 分子量: 543.666
• InChiKey: OXBFAILIZZEZPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,7-diamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid bis-diethylamide 、 苯甲醛 生成 2-amino-7-benzylamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid bis-diethylamide
  参考文献：
  名称：

  N7-Substituted 7-aminoactinomycin D analogs. Synthesis and biological properties

  摘要：

  A series of N7-substituted 7-aminoactinomycin D analogues with alkyl, aralkyl, and heteroaralkyl substituents was synthesized and their biological properties were studied. All of these analogues proved to be 22- to 28-fold less toxic than actinomycin D when tested against human lymphoblastic leukemia cells (CCRF-CEM) in vitro. Against the P388 mouse leukemia in vivo, most of the analogues had activity comparable to actinomycin D and one was significantly more active. The results show that substitutions of this kind do not interfere with the antitumor activity of actinomycin D and may be useful for the design of modified actinomycin D analogues with greater selectivity.

  DOI：

  10.1021/jm00207a021

文献信息

• <i>N</i>-substitution in the 2-amino- and 2,7-diaminophenoxazin-3-one ring system. Application to the preparation of actinomycin D analogs
  作者：Michael Chaykovsky、Edward J. Modest、Sisir K. Sengupta

  DOI：10.1002/jhet.5570140423

  日期：1977.6

  aldehydes in glacial acetic acid to give Schiff bases, which are then reduced with dimethylamine borane. These reactions have been applied to the preparation of N2-benzyl- and 7-benzylaminoactinomycin D.

  描述了通过在DMSO-THF中用二甲基s甲基化物处理来直接2-氨基苯恶嗪-3-酮系统的N 2-单烷基化的方法，该方法通过从2-氨基官能团中提取质子以形成稳定的基团而充当碱。阴离子，然后通过与卤代烷反应进行烷基化。2，7-二氨基苯恶嗪-3-酮体系的选择性N 7-单烷基化可以通过与冰醋酸中的芳族醛反应生成席夫碱实现，然后将其用二甲胺硼烷还原。这些反应已用于制备N 2-苄基和7-苄基氨基放线菌素D。
• N7-Substituted 7-aminoactinomycin D analogs. Synthesis and biological properties
  作者：M. S. Madhavarao、Michael Chaykovsky、Sisir K. Sengupta

  DOI：10.1021/jm00207a021

  日期：1978.9

  A series of N7-substituted 7-aminoactinomycin D analogues with alkyl, aralkyl, and heteroaralkyl substituents was synthesized and their biological properties were studied. All of these analogues proved to be 22- to 28-fold less toxic than actinomycin D when tested against human lymphoblastic leukemia cells (CCRF-CEM) in vitro. Against the P388 mouse leukemia in vivo, most of the analogues had activity comparable to actinomycin D and one was significantly more active. The results show that substitutions of this kind do not interfere with the antitumor activity of actinomycin D and may be useful for the design of modified actinomycin D analogues with greater selectivity.