2-fluoro-4-nitrobenzyl phosphoramide mustard | 1225287-23-9

• 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: 2-fluoro-4-nitrobenzyl phosphoramide mustard
• 英文别名: N-[amino-[(2-fluoro-4-nitrophenyl)methoxy]phosphoryl]-2-chloro-N-(2-chloroethyl)ethanamine
• CAS: 1225287-23-9
• 化学式: C₁₁H₁₅Cl₂FN₃O₄P
• 分子量: 374.136
• InChiKey: SYDMJXOERPEUTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氟-4-硝基苯甲酸 在 sodium tetrahydroborate 、 正丁基锂 、 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-fluoro-4-nitrobenzyl phosphoramide mustard
  参考文献：
  名称：

  Synthesis and structure–activity relationships of nitrobenzyl phosphoramide mustards as nitroreductase-activated prodrugs

  摘要：

  A series of nitrobenzyl phosphoramide mustards and their analogs was designed and synthesized to explore their structure-activity relationships as substrates of nitroreductases from Escherichia coli and trypanosomes and as potential antiproliferative and antiparasitic agents. The position of the nitro group on the phenyl ring was important with the 4-nitrobenzyl phosphoramide mustard (1) offering the best combination of enzyme activity and antiproliferative effect against both mammalian and trypanosomatid cells. A preference was observed for halogen substitutions ortho to benzyl phosphoramide mustard but distinct differences were found in their SAR of substituted 4-nitrobenzyl phosphoramide mustards in E. coli nitroreductase-expressing cells and in trypanosomatids expressing endogenous nitroreductases. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.009

文献信息

• Synthesis and structure–activity relationships of nitrobenzyl phosphoramide mustards as nitroreductase-activated prodrugs
  作者：Longqin Hu、Xinghua Wu、Jiye Han、Lin Chen、Simon O. Vass、Patrick Browne、Belinda S. Hall、Christopher Bot、Vithurshaa Gobalakrishnapillai、Peter F. Searle、Richard J. Knox、Shane R. Wilkinson

  DOI：10.1016/j.bmcl.2011.05.009

  日期：2011.7

  A series of nitrobenzyl phosphoramide mustards and their analogs was designed and synthesized to explore their structure-activity relationships as substrates of nitroreductases from Escherichia coli and trypanosomes and as potential antiproliferative and antiparasitic agents. The position of the nitro group on the phenyl ring was important with the 4-nitrobenzyl phosphoramide mustard (1) offering the best combination of enzyme activity and antiproliferative effect against both mammalian and trypanosomatid cells. A preference was observed for halogen substitutions ortho to benzyl phosphoramide mustard but distinct differences were found in their SAR of substituted 4-nitrobenzyl phosphoramide mustards in E. coli nitroreductase-expressing cells and in trypanosomatids expressing endogenous nitroreductases. (C) 2011 Elsevier Ltd. All rights reserved.