[N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]p-toluidine | 1338600-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]p-toluidine
• 英文别名: N-[anthracen-9-yl(diethoxyphosphoryl)methyl]-4-methylaniline
• CAS: 1338600-14-8
• 化学式: C₂₆H₂₈NO₃P
• 分子量: 433.487
• InChiKey: VMSPMSSHCIZRCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]p-toluidine 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-methyl-N-(anthracene-9-ylmethylene)aniline
  参考文献：
  名称：

  两种新型蒽衍生的 BIS-氨基膦酸酯的合成和 NMR 表征。一些氨基膦酸盐衍生物的碱性水解

  摘要：

  摘要 合成两种带有蒽环的新型双氨基膦酸酯——双[N-甲基(二乙氧基膦酰基)-1-(9-蒽基)]联苯胺 (3) 和 4,4'-双[N-甲基(二乙氧基-膦酰基) -1-(9-anthryl)]diaminodiphenylmethane (4) – 报道了通过 Kabachnik-Fields 反应。这些化合物已通过元素分析、TLC、IR、NMR（1H、13C、31P）和荧光光谱表征。该反应导致两种可能形式（内消旋和外消旋）的混合物，其中主要形成一种非对映异构体。重结晶的化合物 3 和 4 仅由一种非对映异构体组成。在新化合物 4 和三种先前描述的氨基膦酸酯衍生物 5-7 的碱性水解中观察到手性中心的外消旋化和 CP 键的断裂。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要

  DOI：

  10.1080/10426507.2011.638349
• 作为产物：
  描述：

  9-蒽甲醛 以 乙醚 、 苯 为溶剂， 反应 14.0h， 生成 [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]p-toluidine
  参考文献：
  名称：

  Synthesis, antiproliferative activity and genotoxicity of novel anthracene-containing aminophosphonates and a new anthracene-derived Schiff base

  摘要：

  A new Schiff base, 9-anthrylidene-furfurylamine and three novel anthracene-containing alpha-aminophosphonates, [N-methyl(dimethoxyphosphonyl)-1-(9-anthryl)]-p-toluidine, [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]-p-toluidine and [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)] furfurylamine were synthesized. The compounds have been characterized by elemental analysis, TLC, IR, NMR and fluorescent spectra. The aminophosphonates and their synthetic precursors were tested for in vitro antitumor activity on a panel of seven human epithelial cancer cell lines. Safety testing was performed both in vitro (3T3 NRU test) and in vivo on ICR mice for genotoxicity and antiproliferative activity. 9-Anthrylidene-furfurylamine and [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)] furfurylamine were most potent cytotoxic agents towards colon carcinoma cell line HT-29. The latter compound exhibited also antiproliferative activity to HBL-100, MDA-MB-231 and 647-V cells. The aminophosphonate [N-methyl(dimethoxyphosphonyl)-1-(9-anthryl)]-p-toluidine and its synthetic precursor 9-anthrylidene-p-toluidine were found to be cytotoxic to HBL-100 and HT-29 tumor cell lines, respectively. Moderate genotoxic and antiproliferative activity in vivo and low toxicity to Balb/c 3T3 (clone 31) mouse embryo cells were observed for all tested compounds. The subcellular distribution of two tested compounds in a tumor cell culture system was also studied. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.024

文献信息

• Synthesis, antiproliferative activity and genotoxicity of novel anthracene-containing aminophosphonates and a new anthracene-derived Schiff base
  作者：I. Kraicheva、I. Tsacheva、E. Vodenicharova、E. Tashev、T. Tosheva、A. Kril、M. Topashka-Ancheva、I. Iliev、Ts. Gerasimova、K. Troev

  DOI：10.1016/j.bmc.2011.11.024

  日期：2012.1

  A new Schiff base, 9-anthrylidene-furfurylamine and three novel anthracene-containing alpha-aminophosphonates, [N-methyl(dimethoxyphosphonyl)-1-(9-anthryl)]-p-toluidine, [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)]-p-toluidine and [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)] furfurylamine were synthesized. The compounds have been characterized by elemental analysis, TLC, IR, NMR and fluorescent spectra. The aminophosphonates and their synthetic precursors were tested for in vitro antitumor activity on a panel of seven human epithelial cancer cell lines. Safety testing was performed both in vitro (3T3 NRU test) and in vivo on ICR mice for genotoxicity and antiproliferative activity. 9-Anthrylidene-furfurylamine and [N-methyl(diethoxyphosphonyl)-1-(9-anthryl)] furfurylamine were most potent cytotoxic agents towards colon carcinoma cell line HT-29. The latter compound exhibited also antiproliferative activity to HBL-100, MDA-MB-231 and 647-V cells. The aminophosphonate [N-methyl(dimethoxyphosphonyl)-1-(9-anthryl)]-p-toluidine and its synthetic precursor 9-anthrylidene-p-toluidine were found to be cytotoxic to HBL-100 and HT-29 tumor cell lines, respectively. Moderate genotoxic and antiproliferative activity in vivo and low toxicity to Balb/c 3T3 (clone 31) mouse embryo cells were observed for all tested compounds. The subcellular distribution of two tested compounds in a tumor cell culture system was also studied. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and NMR Characterization of Two Novel Anthracene-Derived BIS-Aminophosphonates. Basic Hydrolysis of Some Aminophosphonate Derivatives
  作者：I. Kraicheva、E. Vodenicharova、E. Tashev、T. Tosheva、I. Tsacheva、K. Troev

  DOI：10.1080/10426507.2011.638349

  日期：2012.5

  of only one diastereomer. A racemization at the chiral centers and a cleavage of the C-P bond are observed in the alkaline hydrolysis of the new compound 4 and three previously described aminophosphonate derivatives 5–7. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental

  摘要 合成两种带有蒽环的新型双氨基膦酸酯——双[N-甲基(二乙氧基膦酰基)-1-(9-蒽基)]联苯胺 (3) 和 4,4'-双[N-甲基(二乙氧基-膦酰基) -1-(9-anthryl)]diaminodiphenylmethane (4) – 报道了通过 Kabachnik-Fields 反应。这些化合物已通过元素分析、TLC、IR、NMR（1H、13C、31P）和荧光光谱表征。该反应导致两种可能形式（内消旋和外消旋）的混合物，其中主要形成一种非对映异构体。重结晶的化合物 3 和 4 仅由一种非对映异构体组成。在新化合物 4 和三种先前描述的氨基膦酸酯衍生物 5-7 的碱性水解中观察到手性中心的外消旋化和 CP 键的断裂。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要