(p-Tolyl-{[1-p-tolyl-meth-(E)-ylidene]-amino}-methyl)-phosphonic acid diethyl ester | 871315-36-5

• 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: (p-Tolyl-{[1-p-tolyl-meth-(E)-ylidene]-amino}-methyl)-phosphonic acid diethyl ester
• CAS: 871315-36-5
• 化学式: C₂₀H₂₆NO₃P
• 分子量: 359.405
• InChiKey: YPSZJYALPVTLDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (p-Tolyl-{[1-p-tolyl-meth-(E)-ylidene]-amino}-methyl)-phosphonic acid diethyl ester 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](p-tolyl)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：

  对甲基苯甲醛 在 ammonium hydroxide 作用下， 反应 5.0h， 生成 (p-Tolyl-{[1-p-tolyl-meth-(E)-ylidene]-amino}-methyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  柠檬苦素衍生物用于抗炎治疗的设计、合成以及体外和体内生物学评价

  摘要：

  在这项研究中，柠檬苦素衍生物用于设计具有高药理活性和低毒性的新型抗炎化合物。总共发现、合成了 23 种新的柠檬苦素衍生物，并筛选了它们对脂多糖 (LPS) 处理的 RAW 264.7 细胞的抗炎活性。其中，发现化合物f4活性最高，与柠檬苦素和塞来昔布相比具有更高的效率。随后，我们研究了f4活性的潜在机制，发现它通过阻断 LPS 处理的 RAW 264.7 细胞和小鼠中的 NF-κB/MAPK 信号通路来抑制促炎细胞因子。总之，f4可能是一种很有前途的抗炎先导化合物。

  DOI：

  10.1021/acs.jafc.1c04989

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。
• Synthesis and Herbicidal Activity of O,O-Diethyl N-{4-Methyl-[1,2,3]thiadiazole-5-carbonyl}- 1-amino-1-substitutedbenzyl Phosphonates
  作者：Wu Tang、Zhi-Hua Yu、De-Qing Shi

  DOI：10.1080/10426500903453326

  日期：2010.9.27

  results of a preliminary bioassay (in vitro) indicated that some of the title compounds 3 possessed moderate to good herbicidal activities against dicotyledonous plants (Brassica campestris L) at the concentration of 100 mg/L, and most of these compounds exhibited higher herbicidal activities against dicotyledonous plants (Brassica campestris L) than monocotyledonous plants (Echinochloa crus-galli). Supplemental

  在二环己基碳二亚胺 (DCC) 存在下，通过 O,O-二乙基 α-氨基取代苄基膦酸酯 1 和 4-甲基-[1,2,3] 噻二唑-5-羧酸 2 缩合合成目标化合物 3试剂。它们的结构通过光谱数据（IR、1H NMR、31P NMR、MS）和元素分析得到证实。初步生物测定（体外）结果表明，部分标题化合物3在浓度为100 mg/L时对双子叶植物（Brassica campestris L）具有中至良好的除草活性，其中大部分化合物表现出较高的除草活性对双子叶植物 (Brassica campestris L) 比单子叶植物 (Echinochloa crus-galli) 更有效。补充材料可用于本文。去出版商'
• A Novel Synthesis of Diethyl 1-Aminoarylmethylphosphonates on the Surface of Alumina
  作者：A.R Sardarian*、B Kaboudin

  DOI：10.1016/s0040-4039(97)00396-1

  日期：1997.4

  A novel route has been devised for the preparation of a series of diethyl 1-aminoarylmethylphosphonates. The route involves facile reaction among aromatic aldehydes, diethyl hydrogen phosphite and HMDS on the surface of alumina. (C) 1997 Published by Elsevier Science Ltd.
• Al(OTf)₃as an Efficient Catalyst for One-Pot Synthesis of Primary Diethyl 1-Aminophosphonates Under Solvent-Free Conditions
  作者：Sara Sobhani、Zahra Tashrifi

  DOI：10.1080/00397910802369695

  日期：2008.12.16

  A simple and general method has been developed for the one-pot, three-component synthesis of a variety of primary 1-aminophosphonates catalyzed by Al(OTf)(3) under solvent-free conditions in good to high yields.
• 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.