N,N′-(ethane-1,2-diyl)bis(N-methyl-P,P-diphenylphosphinic amide)

• 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: N,N′-(ethane-1,2-diyl)bis(N-methyl-P,P-diphenylphosphinic amide)
• 英文别名: N,N'-bis(diphenylphosphoryl)-N,N'-dimethylethane-1,2-diamine
• 化学式: C₂₈H₃₀N₂O₂P₂
• 分子量: 488.506
• InChiKey: JMGPLZLDSLPREW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N′-(ethane-1,2-diyl)bis(N-methyl-P,P-diphenylphosphinic amide) 、 二苯基二氯化锡 以 甲醇 、 氯仿 为溶剂， 生成 [Ph₂P(O)NMe-(CH₂)₂-MeNP(O)Ph₂.SnPh₂Cl₂]_n
  参考文献：
  名称：

  Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

  摘要：

  Organotin complexes of bisphosphoramidates were prepared by the reaction of (SnRRRCl)-R-1-R-2-Cl-3 (where R = alkyl/aryl/Cl) and Ph2P(O)XP(O)Ph-2 ligands (where X = diamine). All the compounds were characterized by NMR and IR spectroscopy. X-Ray crystallography confirms that the bridging ligand produces binuclear complexes with SnPh3Cl acceptors in C-a3 and C-a4 and offers a polymeric structure toward SnMe2Cl2 in C-c5. The synthesized compounds were screened for the antibacterial activity against B. cereus and E. coli. Based on the MIC test, the ligands are devoid of antibacterial activity. Notably, among the complexes, triphenyltin adducts exhibited a marked activity only against Gram-positive bacterium B. Cereus (IC50 = 0.78 mu g/mL for C-a3 and C-a5). DFT-QSAR models revealed that the descriptor of the electrophilicity (omega) parameter is correlated with the inhibition activity on B. cereus. The correlation matrix of QSAR models and docking analysis confirmed that the electrophilicity parameter controls the influence of the net charge (Q(Sn)) and polarizability of Sn atom of complexes on the inhibition of B. cereus. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.09.030
• 作为产物：
  描述：

  N,N'-二甲基乙二胺 、 二苯基次膦酰氯 在 三乙胺 作用下， 反应 6.0h， 生成 N,N′-(ethane-1,2-diyl)bis(N-methyl-P,P-diphenylphosphinic amide)
  参考文献：
  名称：

  使用对接，QSAR和动力学研究的新型磷酰胺衍生物作为脲酶抑制剂的合成，晶体结构和生物学评估。

  摘要：

  为了获得一种新型的具有高效力和对尿素酶水解过程具有抗性的磷酰胺抑制剂，我们合成了一系列双磷酰胺衍生物（01-43），并通过各种光谱技术对其进行了表征。使用X射线晶体学研究化合物22和26的晶体结构。评价了化合物对波士豆脲酶的抑制活性，并将其与单磷酰胺衍生物和其他已知的标准抑制剂进行了比较。与单磷酰胺，硫脲和乙酰氧肟酸相比，含芳香胺及其取代衍生物的化合物在IC50 = 3.4-1.91×10-10 nM的范围内表现出非常高的抑制活性。还发现具有PO官能团的衍生物具有比具有PS官能团的衍生物更高的抗脲酶活性。进行了动力学和对接研究，以研究表明这些化合物遵循混合型机理的结合机理，并且由于其扩展的结构，可以覆盖酶的整个结合口袋，从而减少了酶-底物复合物的形成。定量构效关系（QSAR）分析还表明，酶与抑制剂之间的相互作用受芳香环和PO官能团的影响很大。集体地，从实验和理论研究获得的数据表明，这些化合

  DOI：

  10.1016/j.bioorg.2019.01.064

文献信息

• Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)−H Compounds
  作者：Chen Tan、Xinyuan Liu、Huanxin Jia、Xiaowen Zhao、Jian Chen、Zhiyong Wang、Jiajing Tan

  DOI：10.1002/chem.201904237

  日期：2020.1.16

  Herein, we report a highly efficient ZnI2 -triggered oxidative cross-coupling reaction of P(O)-H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up

  在本文中，我们报告了P​​（O）-H化合物与胺类的高效ZnI2触发的氧化交叉偶联反应。该操作简单的方案以高收率和较短的反应时间提供了对次膦酰胺/氨基磷酸酯衍生物的空前通用访问。此外，该反应在温和的条件下进行，避免了使用有害试剂，并且适用于按比例放大的合成以及药物分子的后期功能化。立体特异性偶联也可以从容易获得的光学富集的P（O）-H化合物中获得。
• Relations between Structural and Luminescence Properties of Novel Lanthanide Nitrate Complexes with Bis-phosphoramidate Ligands
  作者：Khodayar Gholivand、Mahdieh Hosseini、Yazdan Maghsoud、Jan Valenta、Ali Asghar Ebrahimi Valmuzi、Agata Owczarzak、Maciej Kubicki、Morteza Jamshidi、Mohammad Kahnouji

  DOI：10.1021/acs.inorgchem.8b03611

  日期：2019.5.6

  Five new bisphosphoramide-based LnIII nitrate complexes [La2(NO3)6L3I]n (1), [Ce2(NO3)6L3I]n (2), [Sm2(NO3)6L3II]n (3), Sm2(NO3)6L3III (4), and Er(NO3)3L2III (5) [LI = piperazine-1,4-diylbis(diphenyl phosphine oxide), LII = N,N′-(ethane-1,2-diyl)bis(N-methyl-P,P-diphenylphosphinic amide, and LIII = N,N′-(ethane-1,2-diyl)bis(P,P-diphenylphosphinic amide)] have been synthesized and characterized by elemental

  五个新的基于双磷酰胺的Ln III硝酸盐络合物[La 2（NO 3）6 L 3 I ] n（1），[Ce 2（NO 3）6 L 3 I ] n（2），[Sm 2（NO 3）6 L 3 II ] n（3），Sm 2（NO 3）6 L 3 III（4）和Er（NO 3）3 L 2 III（5）[ L I =哌嗪-1,4-二基双（二苯基氧化膦），L II = N，N '-（乙烷-1,2-二基）双（N-甲基-P，对-二苯基次膦酰胺，并且L III = N，N ′-（乙烷-1,2-二基）双（P，P-二苯基次膦酰胺）]已通过元素分析，红外光谱，热重分析（TGA）以及单晶X射线和粉末衍射进行了合成和表征。X射线衍射分析的结果显示了新的L III多晶型物，以及固态合成的配合物的结构多样性。配合物1 - 3显示的二维配位聚合物（2D-CP），与蜂窝（6,3）拓扑结构含有层。在这些2D-CP的，每个LN中心（
• Synthesis, crystal structure and biological evaluation of new phosphoramide derivatives as urease inhibitors using docking, QSAR and kinetic studies
  作者：Khodayar Gholivand、Mahsa Pooyan、Fahimeh Mohammadpanah、Foroogh Pirastefar、Peter C. Junk、Jun Wang、Ali Asghar Ebrahimi Valmoozi、Ahmad Mani-Varnosfaderani

  DOI：10.1016/j.bioorg.2019.01.064

  日期：2019.5

  quantitative structure-activity relationship (QSAR) analysis also revealed that the interaction between the enzyme and inhibitor is significantly influenced by aromatic rings and PO functional groups. Collectively, the data obtained from experimental and theoretical studies indicated that these compounds can be developed as appropriate candidates for urease inhibitors in this field.

  为了获得一种新型的具有高效力和对尿素酶水解过程具有抗性的磷酰胺抑制剂，我们合成了一系列双磷酰胺衍生物（01-43），并通过各种光谱技术对其进行了表征。使用X射线晶体学研究化合物22和26的晶体结构。评价了化合物对波士豆脲酶的抑制活性，并将其与单磷酰胺衍生物和其他已知的标准抑制剂进行了比较。与单磷酰胺，硫脲和乙酰氧肟酸相比，含芳香胺及其取代衍生物的化合物在IC50 = 3.4-1.91×10-10 nM的范围内表现出非常高的抑制活性。还发现具有PO官能团的衍生物具有比具有PS官能团的衍生物更高的抗脲酶活性。进行了动力学和对接研究，以研究表明这些化合物遵循混合型机理的结合机理，并且由于其扩展的结构，可以覆盖酶的整个结合口袋，从而减少了酶-底物复合物的形成。定量构效关系（QSAR）分析还表明，酶与抑制剂之间的相互作用受芳香环和PO官能团的影响很大。集体地，从实验和理论研究获得的数据表明，这些化合
• Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates
  作者：Khodayar Gholivand、Ali Asghar EbrahimiValmoozi、Akram Gholami、Michal Dusek、Vaclav Eigner、Sara Abolghasemi

  DOI：10.1016/j.jorganchem.2015.09.030

  日期：2016.3

  Organotin complexes of bisphosphoramidates were prepared by the reaction of (SnRRRCl)-R-1-R-2-Cl-3 (where R = alkyl/aryl/Cl) and Ph2P(O)XP(O)Ph-2 ligands (where X = diamine). All the compounds were characterized by NMR and IR spectroscopy. X-Ray crystallography confirms that the bridging ligand produces binuclear complexes with SnPh3Cl acceptors in C-a3 and C-a4 and offers a polymeric structure toward SnMe2Cl2 in C-c5. The synthesized compounds were screened for the antibacterial activity against B. cereus and E. coli. Based on the MIC test, the ligands are devoid of antibacterial activity. Notably, among the complexes, triphenyltin adducts exhibited a marked activity only against Gram-positive bacterium B. Cereus (IC50 = 0.78 mu g/mL for C-a3 and C-a5). DFT-QSAR models revealed that the descriptor of the electrophilicity (omega) parameter is correlated with the inhibition activity on B. cereus. The correlation matrix of QSAR models and docking analysis confirmed that the electrophilicity parameter controls the influence of the net charge (Q(Sn)) and polarizability of Sn atom of complexes on the inhibition of B. cereus. (C) 2015 Elsevier B.V. All rights reserved.