4-{4-[di(2-chloroethyl)amino]-3-nitrophenyl}butanoic acid

• 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: 4-{4-[di(2-chloroethyl)amino]-3-nitrophenyl}butanoic acid
• 英文别名: 3-nitrochlorambucil；4-[4-[bis(2-chloroethyl)amino]-3-nitrophenyl]butanoic acid
• 化学式: C₁₄H₁₈Cl₂N₂O₄
• 分子量: 349.214
• InChiKey: OPMWLAJJXGJDBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  孕烯醇酮 、 4-{4-[di(2-chloroethyl)amino]-3-nitrophenyl}butanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以60%的产率得到(3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]-3-nitro-phenyl}butyrate
  参考文献：
  名称：

  To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines

  摘要：

  Four ester prodrugs derived from the bifunctional alkylating agent chlorambucil, and one of its nitro-derivatives, 3-nitrochlorambucil conjugated to prasterone and pregnenolone, were synthesized and tested for their cytotoxic activity against eight human cell lines, using the standard MTT assay. A comparison between the esters and the controls, namely chlorambucil and 3-nitrochlorambucil would suggest that all four esters possess to varying degrees, specificity towards the breast adenocarcinoma cell line (MDA-mb468) than the other seven cells' lines tested. The overall findings are encouraging since it infers that these lipophilic esters not only have the ability to traverse specific cell membranes but also exhibit cytotoxicity towards most of the cell lines tested. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.014
• 作为产物：
  描述：

  苯丁酸氮芥 在 nitronium tetrafluoborate 作用下， 以 乙腈 为溶剂， 以60%的产率得到4-{4-[di(2-chloroethyl)amino]-3-nitrophenyl}butanoic acid
  参考文献：
  名称：

  Mann, John; Shervington, Leroy A., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 2961 - 2964

  摘要：

  DOI：

文献信息

• Mann, John; Shervington, Leroy A., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 2961 - 2964
  作者：Mann, John、Shervington, Leroy A.

  DOI：——

  日期：——
• To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines
  作者：Leroy A. Shervington、Nigel Smith、Emma Norman、Timothy Ward、Roger Phillips、Amal Shervington

  DOI：10.1016/j.ejmech.2008.11.014

  日期：2009.7

  Four ester prodrugs derived from the bifunctional alkylating agent chlorambucil, and one of its nitro-derivatives, 3-nitrochlorambucil conjugated to prasterone and pregnenolone, were synthesized and tested for their cytotoxic activity against eight human cell lines, using the standard MTT assay. A comparison between the esters and the controls, namely chlorambucil and 3-nitrochlorambucil would suggest that all four esters possess to varying degrees, specificity towards the breast adenocarcinoma cell line (MDA-mb468) than the other seven cells' lines tested. The overall findings are encouraging since it infers that these lipophilic esters not only have the ability to traverse specific cell membranes but also exhibit cytotoxicity towards most of the cell lines tested. (C) 2008 Elsevier Masson SAS. All rights reserved.