[Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester | 189180-13-0

• 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: [Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester
• 英文别名: diethyl (amino(4-bromophenyl)methyl)phosphonate；α-O,O'-diethyl amino(4-bromophenyl)methylphosphonate；Phosphonic acid, [amino(4-bromophenyl)methyl]-, diethyl ester；(4-bromophenyl)-diethoxyphosphorylmethanamine
• CAS: 189180-13-0
• 化学式: C₁₁H₁₇BrNO₃P
• 分子量: 322.139
• InChiKey: LJYDSUWZTSXUKH-UHFFFAOYSA-N

物化性质

• 沸点：
  408.8±40.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester 在 3-carboxypyridinium dichromate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以95%的产率得到diethyl (4-bromobenzoyl)phosphonate
  参考文献：
  名称：

  重铬酸镍（= 3-羧基重铬酸吡啶鎓; NDC）作为胺和氨基膦酸酯氧化脱氨的有效试剂

  摘要：

  用于从多种类型的胺（伯和仲）和氨基膦酸盐醛，酮，和oxophosphonates的有效合成的新方法通过被描述;氧化脱氨通过nicotinium重铬酸（NDC = 3-羧基吡啶基重铬酸盐）。

  DOI：

  10.1002/hlca.201100404
• 作为产物：
  描述：

  对溴苯甲醛 在 盐酸 、 ammonium acetate 作用下， 以 乙醚 为溶剂， 反应 8.5h， 生成 [Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.12.030

文献信息

• Discovery of novel aminophosphonate derivatives containing pyrazole moiety as potential selective COX-2 inhibitors
  作者：Bo Zhang、Xiu-Ting Hu、Kang-Min Zhou、Yu-Shun Yang、Hai-Liang Zhu

  DOI：10.1016/j.bioorg.2020.104096

  日期：2020.9

  Cyclooxygenase is critical for maintaining physiological functions, whereas overexpression of COX-2 was closely implicated in various cancers. In this study, a series of novel aminophosphonate derivatives containing pyrazole moiety were synthesized with their anti-cancer activity evaluated. In vitro assays of the target compounds showed that Z21 displayed excellent COX-2 inhibitory activity against COX-2 (IC50 = 0

  环氧合酶对于维持生理功能至关重要，而COX-2的过度表达与多种癌症密切相关。在这项研究中，合成了一系列含有吡唑部分的新型氨基膦酸酯衍生物，并评估了其抗癌活性。目标化合物的体外分析表明，Z21对COX-2表现出出色的COX-2抑制活性（IC 50  = 0.22±0.04 µM），对MCF-7细胞具有抗增殖活性（IC 50  = 4.37±0.49 µM）。通过流式细胞术和聚合酶链反应证实了化合物Z21的凋亡诱导。进一步的研究表明，化合物Z21通过线粒体依赖性途径诱导MCF-7细胞凋亡，并参与G2期细胞周期停滞。总体而言，这些结果为COX-2抑制剂的治疗药物设计提供了一些新见识，并表明了选择性COX-2抑制与抗肿瘤活性之间的联系。
• An Efficient Synthesis of Diethyl 1-Aminoalkylphosphonate Hydrochlorides via the Intermediate Diethyl 1-Azidoalkylphosphonates
  作者：Tadeusz Gajda、Maciej Matusiak

  DOI：10.1080/00397919208019072

  日期：1992.8

  Abstract The title compounds 4 have been obtained in high yields in a one-step sequence by the Mitsunobu reaction of diethyl 1-hydroxyalkylphosphonates 1 with hydrazoic acid, and subsequence treatment of the inter-mediate azides 2 with triphenylphosphine, followed by hydrolysis of the iminophosphoranes 3 with water.

  摘要 通过 1-羟烷基膦酸二乙酯 1 与偶氮酸的光信反应，然后用三苯基膦处理中间体叠氮化物 2，然后水解亚氨基膦酸酯，以一步顺序高收率获得了标题化合物 4。 3 用水。
• Oxidative Deamination of α-Aminophosphonates and Amines by Zinc Dichromate Trihydrate (ZnCr2O7˙3H2O) under Solvent-Free Conditions at Room Temperature
  作者：Sara Sobhani、Mahdi Maleki

  DOI：10.1055/s-0029-1219174

  日期：2010.2

  A novel method for the rapid and efficient conversion of a variety ot α-aminophosphonates to α-ketophosphonates using ZnCr 2 O 7 ·3H 2 O via oxidative deamination under solvent-free conditions at room temperature is described. This method is also applicable to the rapid and highly selective oxidation of various types of ordinary amines (primary and secondary) to aldehydes and ketones in good to high

  描述了一种使用 ZnCr 2 O 7 ·3H 2 O 在室温下无溶剂条件下通过氧化脱氨基快速有效地将多种 α-氨基膦酸酯转化为 α-酮膦酸酯的新方法。该方法也适用于各种类型的普通胺（伯胺和仲胺）以良好到高产率快速和高选择性氧化成醛和酮。
• Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization
  作者：Christian V. Stevens、Ellen Van Meenen、Yves Eeckhout、Bart Vanderhoydonck、Wim Hooghe

  DOI：10.1039/b508424e

  日期：——

  The halogen atom transfer radical cyclization (HATRC) has been evaluated on N-(indolylmethyl)trichloroacetamides under Cu(I)Cl catalysis using nitrogen containing ligands. The ring closure leads to the formation of 3,3-spiro-3H-indoles in moderate to good yields by a 5-exo-mechanism. Derivatives with an N-electron withdrawing substituent also lead to a 5-exo-trig and not to a 6-endo-trig cyclization.

  卤素原子转移自由基环化反应（HATRC）在含氮配体的存在下，通过Cu(I)Cl催化作用，对N-(吲哚甲基)三氯乙酰胺进行了评估。环化反应通过5-exo机制进行，形成了中等至良好产率的3,3-螺-3H-吲哚。具有吸电子N取代基的衍生物也导致5-exo-trig环化而非6-endo-trig环化。
• Synthesis, antiproliferative and apoptosis-inducing effects of novel asiatic acid derivatives containing α-aminophosphonates
  作者：Ri-Zhen Huang、Cai-Yi Wang、Jian-Fei Li、Gui-Yang Yao、Ying-Ming Pan、Man-Yi Ye、Heng-Shan Wang、Ye Zhang

  DOI：10.1039/c6ra11397d

  日期：——

  This is an Accepted Manuscript, which has been through the RSC Publishing peer review process and has been accepted for publication. Accepted manuscripts are published online shortly after acceptance. This version of the article will be replaced by the fully edited, formatted and proof read Advance Article as soon as this is available.

  这是已接受的手稿，已通过RSC出版同行评审过程，并已被接受出版。接受的手稿在接受后不久就会在线发布。一旦可用，此版本的文章将被完全编辑，格式化并提供高级阅读的高级文章代替。