2,7-diamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid bis-diethylamide | 57270-58-3

• 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: 2,7-diamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid bis-diethylamide
• 英文别名: 2,7-Diamino-1,9-bis(N,N-diethylcarbamoyl)-4,6-dimethyl-3H-phenoxazin-3-on；2,7-diamino-1-N,1-N,9-N,9-N-tetraethyl-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboxamide
• CAS: 57270-58-3
• 化学式: C₂₄H₃₁N₅O₄
• 分子量: 453.541
• InChiKey: HLVIUHXYGGVURG-UHFFFAOYSA-N

物化性质

• 沸点：
  702.6±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-benzyloxy-N,N-diethyl-4-methyl-2-nitro-benzamide 在 platinum(IV) oxide 硫酸 、 氢气 、 硝酸 作用下， 生成 2,7-diamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid bis-diethylamide
  参考文献：
  名称：

  7-取代的放线菌素D类似物。化学和抑制生长的研究。

  摘要：

  报道了三种7-取代的放线菌素D衍生物的合成和生物学活性。通过新方法合成了三种这样的衍生物7-硝基-，7-氨基-和7-羟基放线菌素D，该方法首先在发色团模型系统中成功进行了测试。其中7-硝基和7-氨基放线菌素D在体外和体内对Ridgway成骨肉瘤以及L1210，P1534和P388鼠白血病对哺乳动物细胞（CCRF-CEM人淋巴细胞白血病）的生长抑制活性进行了测定。在这些系统中，7-取代类似物的抑制活性可与放线菌素D相媲美。另一方面，在体外的两个细菌系统（干酪乳杆菌和阿拉伯乳杆菌）中，这些化合物显示出明显不同的抑制谱来自放线菌素D。

  DOI：

  10.1021/jm00246a001

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。
• 7-Substituted actinomycin D analogs. Chemical and growth-inhibitory studies
  作者：S. K. Sengupta、S. K. Tinter、H. Lazarus、B. L. Brown、E. J. Modest

  DOI：10.1021/jm00246a001

  日期：1975.12

  P388 murine leukemias in vivo. In these systems, the inhibitory activity of the 7-substituted analogs was comparable to actinomycin D. In two bacterial systems ( (L. casei and L. arabinosus) in vitro, on the other hand, these compounds showed inhibitory profiles which are distinctly different from actinomycin D. These studies demonstrate that substitution at the 7 position, which does not interfere with

  报道了三种7-取代的放线菌素D衍生物的合成和生物学活性。通过新方法合成了三种这样的衍生物7-硝基-，7-氨基-和7-羟基放线菌素D，该方法首先在发色团模型系统中成功进行了测试。其中7-硝基和7-氨基放线菌素D在体外和体内对Ridgway成骨肉瘤以及L1210，P1534和P388鼠白血病对哺乳动物细胞（CCRF-CEM人淋巴细胞白血病）的生长抑制活性进行了测定。在这些系统中，7-取代类似物的抑制活性可与放线菌素D相媲美。另一方面，在体外的两个细菌系统（干酪乳杆菌和阿拉伯乳杆菌）中，这些化合物显示出明显不同的抑制谱来自放线菌素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.