diethyl [N-(3-bromophenyl)carbamoyl]methylphosphonate | 1182347-20-1

• 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: diethyl [N-(3-bromophenyl)carbamoyl]methylphosphonate
• 英文别名: N-(3-bromophenyl)-2-diethoxyphosphoryl-acetamide；N-(3-bromophenyl)-2-diethoxyphosphorylacetamide
• CAS: 1182347-20-1
• 化学式: C₁₂H₁₇BrNO₄P
• 分子量: 350.149
• InChiKey: BZIYTQZRXYOGOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 diethyl [N-(3-bromophenyl)carbamoyl]methylphosphonate 、 溴甲苯 在 sodium hydride 作用下， 反应 4.0h， 以32%的产率得到N-benzyl-N-(3-bromophenyl)-2-(tetrahydrofuran-2-yl)acetamide
  参考文献：
  名称：

  C-苄基化的（N-芳基氨基甲酰基）烷基膦酸酯的合成及抗寄生虫活性

  摘要：

  解决了C-苄基化（N-芳基氨基甲酰基）膦酸酯合成中意外的依赖于取代基的区域选择性挑战。所述Ç -benzylated Ñ -furfurylcarbamoyl衍生物显示出低微摩尔Pf的LDH抑制，而之一Ç -benzylated Ñ -arylcarbamoyl类似物反对那加那活性布氏锥虫寄生虫其负责在牛非洲锥虫病。

  DOI：

  10.1016/j.tet.2017.01.045
• 作为产物：
  描述：

  间溴苯胺 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 diethyl [N-(3-bromophenyl)carbamoyl]methylphosphonate
  参考文献：
  名称：

  Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors

  摘要：

  DOXP-reductoisomerase (DXR) is a validated target for the development of antimalarial drugs to address the increase in resistant strains of Plasmodium falciparum. Series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts have been prepared as analogues of the potent DXR inhibitor fosmidomycin. The effects of the carboxamide N-substituents and the length of the methylene linker have been explored using in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays using both EcDXR and PfDXR. These studies indicate an optimal linker length of two methylene units and have confirmed the importance of an additional binding pocket in the PfDXR active site. Insights into the constraints of the PfDXR binding site provide additional scope for the rational design of DXR inhibitors with increased ligand-receptor interactions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.076

文献信息

• Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors
  作者：Taryn Bodill、Anne C. Conibear、Marius K.M. Mutorwa、Jessica L. Goble、Gregory L. Blatch、Kevin A. Lobb、Rosalyn Klein、Perry T. Kaye

  DOI：10.1016/j.bmc.2013.04.076

  日期：2013.7

  DOXP-reductoisomerase (DXR) is a validated target for the development of antimalarial drugs to address the increase in resistant strains of Plasmodium falciparum. Series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts have been prepared as analogues of the potent DXR inhibitor fosmidomycin. The effects of the carboxamide N-substituents and the length of the methylene linker have been explored using in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays using both EcDXR and PfDXR. These studies indicate an optimal linker length of two methylene units and have confirmed the importance of an additional binding pocket in the PfDXR active site. Insights into the constraints of the PfDXR binding site provide additional scope for the rational design of DXR inhibitors with increased ligand-receptor interactions. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and anti-parasitic activity of C -benzylated ( N -arylcarbamoyl)alkylphosphonate esters
  作者：Christiana M. Adeyemi、Michelle Isaacs、Dumisani Mnkandhla、Rosalyn Klein、Heinrich C. Hoppe、Rui W.M. Krause、Kevin A. Lobb、Perry T. Kaye

  DOI：10.1016/j.tet.2017.01.045

  日期：2017.3

  C-benzylated (N-arylcarbamoyl)phosphonate esters have been resolved. The C-benzylated N-furfurylcarbamoyl derivative showed low micromolar PfLDH inhibition, while one of the C-benzylated N-arylcarbamoyl analogues was active against Nagana Trypanosoma brucei parasites which are responsible for African trypanosomiasis in cattle.

  解决了C-苄基化（N-芳基氨基甲酰基）膦酸酯合成中意外的依赖于取代基的区域选择性挑战。所述Ç -benzylated Ñ -furfurylcarbamoyl衍生物显示出低微摩尔Pf的LDH抑制，而之一Ç -benzylated Ñ -arylcarbamoyl类似物反对那加那活性布氏锥虫寄生虫其负责在牛非洲锥虫病。