(2S)-N-{4-[4-(4-(3-(diethoxyphosphoryl)propyl)piperazin-1-yl)butyloxy]-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal | 1033090-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-N-{4-[4-(4-(3-(diethoxyphosphoryl)propyl)piperazin-1-yl)butyloxy]-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS: 1033090-67-3
• 化学式: C₃₂H₅₇N₄O₆PS₂
• 分子量: 688.934
• InChiKey: VQKPAWWSRZOEPT-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  45.0
• 可旋转键数：
  21.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  106.8
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S)-N-{4-[4-(4-(3-(diethoxyphosphoryl)propyl)piperazin-1-yl)butyloxy]-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 在 calcium carbonate 、 mercury dichloride 作用下， 以 水 、 乙腈 为溶剂， 以68%的产率得到(11aS)-7-methoxy-8-[4-(4-(3-(diethoxyphosphoryl)propyl)piperazin-1-yl)butyloxy]-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
  参考文献：
  名称：

  Phosphonate-linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: Synthesis, DNA-binding affinity and cytotoxicity

  摘要：

  Pyrrolobenzodiazepine-diethylphosphonate conjugates have been designed and synthesized that link through two different types of spacers that are simple alkane chain and also a piperazine moiety side-armed with the alkane chains. These pyrrolobenzodiazepine conjugates have exhibited remarkable DNA-binding affinity and improved solubility in water, a representative compound 7d showing promising in vitro cytotoxicity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.040
• 作为产物：
  描述：

  (2S)-N-{4-[4-(4-(3-(diethoxyphosphoryl)propyl)piperazin-1-yl)butyloxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以75%的产率得到(2S)-N-{4-[4-(4-(3-(diethoxyphosphoryl)propyl)piperazin-1-yl)butyloxy]-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal
  参考文献：
  名称：

  Phosphonate-linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: Synthesis, DNA-binding affinity and cytotoxicity

  摘要：

  Pyrrolobenzodiazepine-diethylphosphonate conjugates have been designed and synthesized that link through two different types of spacers that are simple alkane chain and also a piperazine moiety side-armed with the alkane chains. These pyrrolobenzodiazepine conjugates have exhibited remarkable DNA-binding affinity and improved solubility in water, a representative compound 7d showing promising in vitro cytotoxicity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.040