diethyl {N-[3-(hydroxymethyl)phenyl]carbamoyl}ethylphosphonate | 1444512-12-2

• 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-(hydroxymethyl)phenyl]carbamoyl}ethylphosphonate
• 英文别名: 3-diethoxyphosphoryl-N-[3-(hydroxymethyl)phenyl]propanamide
• CAS: 1444512-12-2
• 化学式: C₁₄H₂₂NO₅P
• 分子量: 315.306
• InChiKey: BOILEJKRRHDOFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 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：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氨基苯甲醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 diethyl {N-[3-(hydroxymethyl)phenyl]carbamoyl}ethylphosphonate
  参考文献：
  名称：

  N-苄基化的（N-芳基氨基甲酰基）烷基膦酸衍生物的合成和抗疟活性。

  摘要：

  已经制备了一系列新颖且易于获得的N-苄基化（N-芳基氨基甲酰基）烷基膦酸酯和相关化合物作为潜在的抗疟剂。生物测定法表明，这些化合物中的一些对恶性疟原虫表现出有希望的活性，并且对HeLa细胞没有明显的生长抑制作用。

  DOI：

  10.1016/j.bmc.2016.04.021

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 antimalarial activity of N-benzylated (N-arylcarbamoyl)alkylphosphonic acid derivatives
  作者：Christiana M. Adeyemi、Faridoon、Michelle Isaacs、Dumisani Mnkandhla、Heinrich C. Hoppe、Rui W.M. Krause、Perry T. Kaye

  DOI：10.1016/j.bmc.2016.04.021

  日期：2016.12

  A series of novel and readily accessible N-benzylated (N-arylcarbamoyl)alkylphosphonate esters and related compounds have been prepared as potential antimalarial agents. Bioassays reveal that some of these compounds exhibit promising activity against Plasmodium falciparum, and exhibit no significant growth inhibition of HeLa cells.

  已经制备了一系列新颖且易于获得的N-苄基化（N-芳基氨基甲酰基）烷基膦酸酯和相关化合物作为潜在的抗疟剂。生物测定法表明，这些化合物中的一些对恶性疟原虫表现出有希望的活性，并且对HeLa细胞没有明显的生长抑制作用。