5-hydroxymethyl-2-nitrobenzamide | 782496-85-9

• 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: 5-hydroxymethyl-2-nitrobenzamide
• 英文别名: 5-(hydroxymethyl)-2-nitrobenzamide
• CAS: 782496-85-9
• 化学式: C₈H₈N₂O₄
• 分子量: 196.163
• InChiKey: DUCYZAIFQRCQAR-UHFFFAOYSA-N

物化性质

• 熔点：
  143-145 °C
• 沸点：
  380.8±32.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxymethyl-2-nitrobenzamide 在 正丁基锂 、 氨 作用下， 以 四氢呋喃 为溶剂， 生成 3-carboxamide-4-nitrobenzyl N,N-bis(2-chloroethyl)phosphordiamidate
  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
• 作为产物：
  描述：

  5-(羟甲基)-2-硝基苯甲酸甲酯 在 氨 作用下， 以 甲醇 为溶剂， 反应 144.0h， 以73%的产率得到5-hydroxymethyl-2-nitrobenzamide
  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

文献信息

• PIPERIDINE DERIVATIVES AND THEIR USE AS ANTAGONISTS OF TACHYKININS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1472243A1

  公开（公告）日：2004-11-03
• [EN] PIPERIDINE DERIVATIVES AND THEIR USE AS ANTAGONISTS OF TACHYKININS<br/>[FR] DERIVES DE PIPERIDINE ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DES TACHYKININES
  申请人：GLAXO GROUP LTD

  公开号：WO2003066621A1

  公开（公告）日：2003-08-14

  The present invention relates to piperidine derivatives of formula (I); wherein R represents halogen or C 1-4 alkyl; R1 represents hydrogen or C1-4 alkyl; R2 represents hydrogen, C1-4 alkyl; R3 represents hydrogen, C1-4 alkyl;R4 represents trifluoromethyl, C1-4 alkyl, C1-4 alkoxy, trifluoromethoxy or halogen; R5 represents hydrogen, C1-4 alkyl, C3-7 cycloalkyl, C(O)R6 or S(O)2R6;R6 represents C 1-4 alkyl or C3-7 cycloalkyl; m is zero or an integer from 1 to 3; n is an integer from 1 to 3; p is an integer from 1 to 2; X and Y are independently C(O) or CH2; provided that i) X and Y are not both C(O) and ii) when X and Y are both CH2 and p is 1, R5 is not hydrogen, C1-4 alkyl or C(O)R6 ; and pharmaceutically acceptable salts and solvates thereof, the process for their preparation and their use in the treatment of condition mediated by tachykinins.
• 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。
• 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.