N-(4-氟苯基亚甲基)-1-氨基(4-氟苯基)乙基膦酸二乙酯 | 909722-64-1

• 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-(4-氟苯基亚甲基)-1-氨基(4-氟苯基)乙基膦酸二乙酯
• 英文名称: diethyl N-(4-fluorophenylmethylene)-1-amino (4-fluorophenyl)ethylphosphonate
• 英文别名: N-[diethoxyphosphoryl-(4-fluorophenyl)methyl]-1-(4-fluorophenyl)methanimine
• CAS: 909722-64-1
• 化学式: C₁₈H₂₀F₂NO₃P
• 分子量: 367.332
• InChiKey: CZTFCTUIGKPMQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-氟苯基亚甲基)-1-氨基(4-氟苯基)乙基膦酸二乙酯 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 O,O-diethyl [2-(4,6-dimethoxypyrimidin-2-yloxy)phenoxyamino](4-fluorophenyl)methylphosphonate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Phosphonates Derivatives of As Potential Antitumor Agents

  摘要：

  DOI：

  10.1080/10426507.2011.558363
• 作为产物：
  描述：

  对氟苯甲醛 在 ammonium hydroxide 作用下， 反应 4.0h， 生成 N-(4-氟苯基亚甲基)-1-氨基(4-氟苯基)乙基膦酸二乙酯
  参考文献：
  名称：

  Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113474

文献信息

• TMSCl-Promoted Addition of Diethyl Phosphite to an Imine for the Synthesis of Bis[1-diethoxyphosphorylalkyl]amines
  作者：Babak Kaboudin、Khavar Moradi

  DOI：10.1055/s-2006-942432

  日期：——

  A convenient preparative approach for the synthesis of bis[1-diethoxyphosphorylalkyl]amines has been developed. Treatment of aromatic aldehydes with ammonia and reaction with diethyl phosphite gives diethyl aryl[(arylmethylidene)amino]methylphosphonates, which can be easily reacted with diethyl phosphite in the presence of chlorotrimethylsilane to give bis[1-diethoxyphosphor­ylalkyl]amines. This method is easy, rapid, and good-yielding for the synthesis of bis[1-diethoxyphosphorylalkyl]amines from simple starting materials.

  已开发出一种简便的制备双[1-二乙氧基膦酰基烷基]胺类化合物的方法。将芳香醛与氨反应，再与二乙基亚磷酸酯反应，得到二乙基芳基[(芳基亚甲基)氨基]甲基膦酸酯，这些化合物在氯三甲基硅烷存在下可轻松与二乙基亚磷酸酯反应，生成双[1-二乙氧基膦酰基烷基]胺。该方法简便、快速且产率高，适合从简单原料合成双[1-二乙氧基膦酰基烷基]胺。
• Surface-Mediated Solid Phase Reactions: A Simple and New Method for the Synthesis of<i>α</i>-Aminophosphonates under Solvent-Free Conditions
  作者：Babak Kaboudin

  DOI：10.1246/cl.2001.880

  日期：2001.9

  Alumina-supported ammonium formate was found to be an efficient reagent for the synthesis of 1-aminophosphonates from aldehydes and diethyl phosphite. This method is an easy, rapid and high-yieldin...

  发现氧化铝负载的甲酸铵是从醛和亚磷酸二乙酯合成 1-氨基膦酸酯的有效试剂。这种方法是一种简单、快速和高产...
• Synthesis of a Novel Class of β-Lactam Derivatives of 1-Aminophosphonates by Staudinger Ketene-Imine [2+2]-Cycloaddition Reaction
  作者：Babak Kaboudin、Mohammad Afsharinezhad

  DOI：10.1055/s-0030-1257889

  日期：2010.10

  A novel class of β-lactam derivatives of 1-aminophosphonates was synthesized by Staudinger [2+2] cycloaddition reaction of ketenes with imines derived from 1-aminophosphonates. Treatment of aromatic aldehydes with ammonia and diethyl phosphite followed by a reaction with ketenes, which are generated from the appropriate acid chloride and a tertiary amine, gave a novel class of β-lactam derivatives of

  通过烯酮与衍生自1-氨基膦酸酯的亚胺的斯托丁格[2 + 2]环加成反应，合成了一类新型的1-氨基膦酸酯的β-内酰胺衍生物。用氨和亚磷酸二乙酯处理芳香醛，然后与由适当的酰氯和叔胺生成的乙烯酮反应，得到一类新型的1-氨基膦酸酯的β-内酰胺衍生物。环加成反应的主要产物或某些情况下的唯一产物是顺式-β-内酰胺。 1-氨基膦酸酯-β-内酰胺-烯酮-亚胺-[2 + 2]-环加成反应
• Coumarin-containing aminophosphonates bridged with chiral side chain: synthesis and influence of chirality on cytotoxicity and DNA binding
  作者：Ya-Jun Li、Man-Yi Ye、Ri-Zhen Huang、Gui-Yang Yao、Ying-Ming Pan、Zhi-Xin Liao、Heng-Shan Wang

  DOI：10.1007/s00044-013-0899-3

  日期：2014.6

  A series of novel coumarin-containing alpha-aminophosphonates with two chiral centers were synthesized and a single-crystal structure of compound 8g (8g', (R)-diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(2-bromophenyl)methylphosphonate) was obtained. The in vitro antitumor activities of compound 8a-8g' against human pulmonary carcinoma cell line (A549), human nasopharyngeal carcinoma (human KB), and human lung adenocarcinoma (MGC-803) cell lines were evaluated. Some compounds showed relatively high cytotoxicity. Compared with 8g, 8g' exhibited an improved activity against three tumor cells, which was evidenced by the IC50 that was four- to five-fold lower than those for 8g. The influence of chirality was also observed in DNA-binding assay of 8g and 8g'. 8g' exhibited higher binding constant (1.96 x 10(3) M-1) as compared to 8g (1.69 x 10(3) M-1).
• Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates
  作者：Gui-yang Yao、Man-yi Ye、Ri-zhen Huang、Ya-jun Li、Ying-ming Pan、Qing Xu、Zhi-Xin Liao、Heng-shan Wang

  DOI：10.1016/j.bmcl.2013.12.030

  日期：2014.1

  Several rhein alpha-aminophosphonates conjugates (5a-5q) were synthesized and evaluated for in vitro cytotoxicity against HepG-2, CNE, Spca-2, Hela and Hct-116 cell lines. Some compounds showed relatively high cytotoxicity. Especially, compound 5i exhibited the strongest cytotoxicity against Hct-116 cells (IC50 was 5.32 mu M). All the synthesized compounds exhibited low cytotoxicity against HUVEC cells. The mechanism of compound 5i was preliminarily investigated by Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which indicated that the compound 5i induced apoptosis in Hct-116 cancer cells. Cell cycle analysis showed that these compound 5i mainly arrested Hct-116 cells in G1 stage. The effects of 5i on the activation of caspases expression indicated that 5i might induce apoptosis via the membrane death receptor pathways. In addition, the binding properties of a model analog 5i to DNA were investigated by methods (UV-vis, fluorescence, CD spectroscopy and FRET-melting) in compare with that of rhein. Results indicated that 5i showed moderate ability to interact ct-DNA. (C) 2013 Elsevier Ltd. All rights reserved.