1-(4-bromophenyl)-N-[(4-bromophenyl)-diethoxyphosphorylmethyl]methanimine | 871315-33-2

• 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: 1-(4-bromophenyl)-N-[(4-bromophenyl)-diethoxyphosphorylmethyl]methanimine
• CAS: 871315-33-2
• 化学式: C₁₈H₂₀Br₂NO₃P
• 分子量: 489.143
• InChiKey: AKVIYQIDHMVYOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 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：
  0.28
• 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：

  1-(4-bromophenyl)-N-[(4-bromophenyl)-diethoxyphosphorylmethyl]methanimine 在 对甲苯磺酸 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 [Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  由芳族醛合成1-氨基膦酸酯的简便方法

  摘要：

  已经开发了一种简单，有效，可能的工业方法，用于从简单的起始原料合成1-氨基膦酸。如下所述，用氨处理芳族醛并与亚磷酸二乙酯反应得到N-（芳基亚甲基）-1-氨基芳基甲基膦酸二乙酯，其可以容易地水解为1-氨基芳基甲基膦酸二乙酯。从简单的起始原料合成1-氨基烷基膦酸酯的方法简便，快速且产率高。

  DOI：

  10.1016/j.tetlet.2005.03.037
• 作为产物：
  描述：

  对溴苯甲醛 、 亚磷酸二乙酯 在 ammonium acetate 作用下， 反应 9.0h， 生成 1-(4-bromophenyl)-N-[(4-bromophenyl)-diethoxyphosphorylmethyl]methanimine
  参考文献：
  名称：

  Novel Coumarin-Containing Aminophosphonatesas Antitumor Agent: Synthesis, Cytotoxicity, DNA-Binding and Apoptosis Evaluation

  摘要：

  合成了一系列含有香豆素结构的α-氨基膦酸酯类新化合物，并评估了它们对体外人结直肠癌（HCT-116）、人鼻咽癌（人KB）和人肺腺癌（MGC-803）细胞系的抗癌活性。与7-羟基-4-甲基香豆素（4-MU）相比，大多数衍生物显示出增强的抗癌活性。化合物8j（二乙基1-（3-（4-甲基-2-氧-2H-色烯-7-基氧）丙酰胺基）-1-苯乙基膦酸酯），对HCT-116细胞系的IC50值为8.68 μM，是其未取代母体化合物的约12倍。机制研究表明，8c、8d、8f和8j通过诱导G1期细胞周期阻滞来实现细胞凋亡。此外，进一步揭示了化合物8j诱导HCT-116细胞凋亡的机制，表明化合物8j通过激活caspase-9和caspase-3引起细胞凋亡，并改变抗凋亡和促凋亡蛋白。DNA结合实验表明，某些衍生物通过嵌插与DNA结合。结果似乎暗示了香豆素和氨基膦酸酯之间存在重要的协同效应，这可能有助于氨基膦酸酯部分的强螯合特性。

  DOI：

  10.3390/molecules200814791

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.
• 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).