acetic acid 2-bromomethyl-5-nitrophenyl ester | 98590-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: acetic acid 2-bromomethyl-5-nitrophenyl ester
• 英文别名: acetic acid-(2-bromomethyl-5-nitro-phenyl ester)；Essigsaeure-(2-brommethyl-5-nitro-phenylester)；α-Brom-4-nitro-2-acetoxy-toluol；4-Nitro-2-acetoxy-1-brommethyl-benzol；(5-Nitro-2-brommethyl-phenyl)-acetat；4-Nitro-2-acetoxy-benzylbromid；2-Acetoxy-4-nitrobenzyl bromide；[2-(bromomethyl)-5-nitrophenyl] acetate
• CAS: 98590-42-2
• 化学式: C₉H₈BrNO₄
• 分子量: 274.071
• InChiKey: SGFGJVMOMRHJQB-UHFFFAOYSA-N

物化性质

• 熔点：
  82 °C
• 沸点：
  379.1±37.0 °C(Predicted)
• 密度：
  1.627±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetic acid 2-bromomethyl-5-nitrophenyl ester 在 palladium on activated charcoal 18-冠醚-6 、 氢气 、 三乙胺 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Nitrobenzocyclophosphamides as potential prodrugs for bioreductive activation: synthesis, stability, enzymatic reduction, and antiproliferative activity in cell culture

  摘要：

  In efforts to obtain potential anticancer prodrugs for gene-directed enzyme prodrug therapy using Eschericia coli nitroreductase, a series of four benzocyclophosphamide analogues were designed and synthesized incorporating a strategically placed nitro group in a position para to the benzylic carbon for reductive activation. All four analogues were found to be stable in phosphate buffer at pH 7.4 and 37 degreesC and were good substrates of E. coli nitroreductase with half lives between 7 and 24 min at pH 7.0 and 37 degreesC. However, only two analogues 6a and 6c, both with a benzylic oxygen in the phosphorinane ring para to the nitro group, showed a modest 33-36-fold enhanced cytotoxicity in E. coli nitroreductase-expressing cells. These results suggest that good substrate activity and the para benzylic oxygen are required for activation by E. coli nitroreductase. Compounds 6a and 6c represent a new structure type for reductive activation and a lead for further modification in the development of better analogues with improved selective toxicity to be used in gene-directed enzyme prodrug therapy. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00459-0
• 作为产物：
  描述：

  5-硝基-2-甲基苯酚 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 20.0h， 生成 acetic acid 2-bromomethyl-5-nitrophenyl ester
  参考文献：
  名称：

  Nitrobenzocyclophosphamides as potential prodrugs for bioreductive activation: synthesis, stability, enzymatic reduction, and antiproliferative activity in cell culture

  摘要：

  In efforts to obtain potential anticancer prodrugs for gene-directed enzyme prodrug therapy using Eschericia coli nitroreductase, a series of four benzocyclophosphamide analogues were designed and synthesized incorporating a strategically placed nitro group in a position para to the benzylic carbon for reductive activation. All four analogues were found to be stable in phosphate buffer at pH 7.4 and 37 degreesC and were good substrates of E. coli nitroreductase with half lives between 7 and 24 min at pH 7.0 and 37 degreesC. However, only two analogues 6a and 6c, both with a benzylic oxygen in the phosphorinane ring para to the nitro group, showed a modest 33-36-fold enhanced cytotoxicity in E. coli nitroreductase-expressing cells. These results suggest that good substrate activity and the para benzylic oxygen are required for activation by E. coli nitroreductase. Compounds 6a and 6c represent a new structure type for reductive activation and a lead for further modification in the development of better analogues with improved selective toxicity to be used in gene-directed enzyme prodrug therapy. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00459-0

文献信息

• Nitroaryl phosphoramide compositions and methods for targeting and inhibiting undesirable cell growth or proliferation
  申请人：——

  公开号：US20040214798A1

  公开（公告）日：2004-10-28

  The present invention relates to nitroaryl-substituted phosphoramide prodrug compounds and methods of producing the same for use in targeting and inhibiting undesirable cell growth or proliferation.

  本发明涉及硝基芳基取代的磷酰胺前药化合物及其制备方法，用于靶向和抑制不良细胞生长或增殖。
• Vargha et al., Acta Chimica Academiae Scientiarum Hungaricae, 1954, vol. 4, p. 345,350
  作者：Vargha et al.

  DOI：——

  日期：——
• 4-Aminosalicylaldehyde
  作者：A. A. Goldberg、H. A. Walker

  DOI：10.1039/jr9540002540

  日期：——
• Preparation of 4-Nitrosalicylaldehyde
  作者：J. R. Segesser、M. Calvin

  DOI：10.1021/ja01256a024

  日期：1942.4
• US6080587A
  申请人：——

  公开号：US6080587A

  公开（公告）日：2000-06-27