2-amino-1,9-bis(N,N-diethylcarbamoyl)-4,6-dimethyl-7-(cyclopropylmethoxy)-3H-phenoxazin-3-one | 112599-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-amino-1,9-bis(N,N-diethylcarbamoyl)-4,6-dimethyl-7-(cyclopropylmethoxy)-3H-phenoxazin-3-one
• 英文别名: 2-amino-7-(cyclopropylmethoxy)-1-N,1-N,9-N,9-N-tetraethyl-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboxamide
• CAS: 112599-09-4
• 化学式: C₂₈H₃₆N₄O₅
• 分子量: 508.618
• InChiKey: IJOWZFYFAUFXQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-amino-1-N,1-N,9-N,9-N-tetraethyl-3-hydroxy-4,6-dimethyl-7-oxophenoxazine-1,9-dicarboxamide 、 溴甲基环丙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以22%的产率得到2-amino-1,9-bis(N,N-diethylcarbamoyl)-4,6-dimethyl-7-(cyclopropylmethoxy)-3H-phenoxazin-3-one
  参考文献：
  名称：

  Synthesis and biological properties of actinomycin D chromophoric analogs substituted at carbon 7 with aziridine and cyclopropyl functions

  摘要：

  The growing importance of functionalized tricyclic rings, e.g., cyclopropyl and aziridine, in numerous organic biomolecules led us to develop syntheses of novel actinomycin D (AMD) analogues substituted with aziridine and cyclopropyl functions. Reaction of 7-hydroxyactinomycin D with 1-aziridineethyl iodide and bromomethylcycloporopane afforded the desired 7-[2-(1-aziridinyl)ethoxy] and cyclopropylmethoxy analogues, respectively. Calf thymus DNA binding of these analogues was comparable to that of AMD as examined by UV-vis difference spectral measurements, CD techniques, and relaxation of supercoiled closed circular SV40 DNA, indicating an intercalative mode of binding to the DNA duplex. Thermal denaturation of DNA experiments employing higher temperatures than room temperature exhibit a thermal lability of the DNA analogue complexes, suggestive of a probable covalent bond formation with DNA bases. The analogues were found to be 1/4-1/40 as cytotoxic to human lymphoblastic CCRF-CEM leukemia and B16 melanoma cells in vitro as AMD, with ID50 values in the nanomolar concentration range.

  DOI：

  10.1021/jm00399a018

文献信息

• SEHGAL, RAJ K.;ALMASSIAN, BIJAN;ROSENBAUM, DAVID P.;ZADROZNY, RUTH;SENGUP+, J. MED. CHEM., 31,(1988) N 4, 790-793
  作者：SEHGAL, RAJ K.、ALMASSIAN, BIJAN、ROSENBAUM, DAVID P.、ZADROZNY, RUTH、SENGUP+

  DOI：——

  日期：——