N-[2-(羟甲基)-5-硝基苯基]乙酰胺 | 651733-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[2-(羟甲基)-5-硝基苯基]乙酰胺
• 英文名称: 2-acetamido-4-nitrobenzyl alcohol
• 英文别名: N-[2-(hydroxymethyl)-5-nitrophenyl]acetamide
• CAS: 651733-13-0
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: MDTICKRXNZLAHC-UHFFFAOYSA-N

物化性质

• 沸点：
  477.0±40.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(羟甲基)-5-硝基苯基]乙酰胺 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 20.0h， 以100%的产率得到2-氨基-4-硝基苯甲醇
  参考文献：
  名称：

  Nitroaryl phosphoramide compositions and methods for targeting and inhibiting undesirable cell growth or proliferation

  摘要：

  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。

  公开号：

  US20040214798A1
• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 四氯化碳 、 氯仿 、 水 为溶剂， 反应 29.0h， 生成 N-[2-(羟甲基)-5-硝基苯基]乙酰胺
  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。
• [EN] POLYSUBSTITUTED ANILINOPYRIMIDINE DERIVATIVE AND PREPARATION METHOD AND APPLICATION THEREOF<br/>[FR] DÉRIVÉ D'ANILINOPYRIMIDINE POLYSUBSTITUÉ, SON PROCÉDÉ DE PRÉPARATION ET SON APPLICATION<br/>[ZH] 一种多取代苯氨基嘧啶衍生物及其制备方法和用途
  申请人：HANGZHOU BIO CREATIVITY PHARMA TECH CO LTD

  公开号：WO2020135507A1

  公开（公告）日：2020-07-02

  本发明公开了一种具有通式Ⅰ结构的多取代苯氨基嘧啶衍生物及其制备方法和用途，该类衍生物及其药学上可接受的盐或溶剂化合物是激酶CDK4、CDK6和/或CDK9抑制剂，可更广泛地用于癌症的治疗，具有巨大的临床应用价值。
• Nitroaryl Phosphoramides as Novel Prodrugs for <i>E. coli</i> Nitroreductase Activation in Enzyme Prodrug Therapy
  作者：Longqin Hu、Chengzhi Yu、Yongying Jiang、Jiye Han、Zhuorong Li、Patrick Browne、Paul R. Race、Richard J. Knox、Peter F. Searle、Eva I. Hyde

  DOI：10.1021/jm034133h

  日期：2003.11.1

  Cyclic and acyclic nitroaryl phosphoramide mustard analogues were activated by E. coli nitroreductase, an enzyme explored in GDEPT. The more active acyclic 4-nitrobenzyl phosphoramide mustard (7) showed 167 500x selective cytotoxicity toward nitroreductase-expressing V79 cells with an IC50 as low as 0.4 nM. This is about 100 x more active and 27x more selective than CB1954 (1). The superior activity was attributed to its better substrate activity (k(cat)/K-m 19x better than 1) and/or excellent cytotoxicity of phosphoramide mustard released.
• Nitrobenzocyclophosphamides as potential prodrugs for bioreductive activation: synthesis, stability, enzymatic reduction, and antiproliferative activity in cell culture
  作者：Z Li

  DOI：10.1016/s0968-0896(03)00459-0

  日期：2003.9.15

  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.