N,N-bis<2-<(methylsulfonyl)oxy>ethyl>aniline | 22964-38-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis<2-<(methylsulfonyl)oxy>ethyl>aniline
• 英文别名: 2-[(2-methylsulfonyloxyethyl)phenylamino]ethyl methanesulfonate；(phenylazanediyl)bis(ethane-2,1-diyl)dimethanesulfonate；N,N-bis(2-(methylsulfonyloxy)ethyl)aniline；NSC71035；2.2'-Phenylimino-diaethyl-dimethansulfonat；2-[N-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate
• CAS: 22964-38-1
• 化学式: C₁₂H₁₉NO₆S₂
• 分子量: 337.418
• InChiKey: CLTRRIBMLYCHGK-UHFFFAOYSA-N

物化性质

• 熔点：
  98-105 °C
• 沸点：
  567.9±35.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-bis<2-<(methylsulfonyl)oxy>ethyl>aniline 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N,N-二(2-碘乙基)苯胺
  参考文献：
  名称：

  Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines

  摘要：

  A series of aniline mustards with a wide range of electron-donating and -withdrawing substituents in the 3- and 4-positions has been synthesized and evaluated for cytotoxicity in cell culture to examine the potential of using nitro group deactivated nitrogen mustards for the design of novel hypoxia-selective anticancer drugs (Denny, W. A.; Wilson, W. R. J. Med. Chem. 1986, 29, 879). Hydrolytic half-lives in tissue culture media, determined by bioassay against a cell line (UV4) defective in the repair of DNA interstrand cross-links showed the expected dependence on the Hammett electronic parameter, sigma, varying from 0.13 h for the 4-amino analogue to greater than 100 h for analogues with strongly electron-withdrawing substituents. Cytotoxic potencies in aerobic UV4 cultures showed a similar dependence on sigma. This dependence predicted that the 4-nitroaniline mustard would be 7200-fold less potent than its potential six-electron reduction product, the 4-amino compound, in growth inhibition assays using a 1-h drug exposure. The measured differential was much lower (225-fold) because of the instability of the latter compound, but a differential of 17,500-fold was observed in the initial rate of killing by using a clonogenic assay. The potential for formation of reactive mustards by reduction to the amine or hydroxylamine was demonstrated by the 4-nitroso compound, which had an aerobic toxicity similar to that of the amine. Although these features confirmed the original rationale, the 3-nitro- and 4-nitroaniline mustards had only minimal hypoxic selectivity against UV cells. Toxicity to hypoxic cells appears to be limited by the low reduction potentials of these compounds and consequent lack of enzymatic nitroreduction. However, this study has demonstrated that nitro groups can be used to latentiate aromatic nitrogen mustards and indicates that examples with higher reduction potentials could provide useful hypoxia-selective therapeutic agents.

  DOI：

  10.1021/jm00163a019
• 作为产物：
  描述：

  苯胺 在 三乙胺 、 calcium carbonate 、 potassium iodide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 N,N-bis<2-<(methylsulfonyl)oxy>ethyl>aniline
  参考文献：
  名称：

  Synthesis and structure–analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ)

  摘要：

  A series of monospirocyclopiperazinium salts were designed and synthesized to search for a peripherally-acting analgesic drug with low side effects. Extensive SAR studies revealed that a suitable (NRR3)-R-2 was critical for the analgesic activity, which might be beneficial to expose the cationic nitrogen to bind to the receptor, and possibly interact with the receptor via pi-pi interaction. Introduction of substituting group on the N-4-phenyl ring could improve the activity, and the best position was the 4-position. Compound 14n showed more potent analgesic activity (63%, 20 mu M/kg, sc) and holds promise for development as a mechanically new analgesic drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.052

文献信息

• Multi‐Channel Receptors and Their Relation to Guest Chemosensing and Reconfigurable Molecular Logic Gates
  作者：Diego Jiménez、Ramón Martínez‐Máñez、Félix Sancenón、José V. Ros‐Lis、Juan Soto、Ángel Benito、Eduardo García‐Breijo

  DOI：10.1002/ejic.200400844

  日期：2005.6

  Significant anodic shifts of both reduction and oxidation waves were found in the presence of certain metal cations. The relationship of these multiple-channel signalling receptors with guest chemosensing and reconfigurable molecular-based logic gates is discussed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  合成和表征的多通道受体家族包含锚定到 1-氨基苯基-1,2,2-三氰基乙烯基的冠阳离子结合位点。配体 L1-L6 带有一个 1-氨基苯基-1,2,2-三氰基乙烯支架，它同时是一个氧化还原活性基团（在中等电位下显示还原过程）和 1-氨基苯基-1,2 中的受体部分， 2-三氰基乙烯发色团。此外，染料 L1-L6 也显示荧光发射。研究了在金属阳离子 Ag+、Cd2+、Cu2+、Fe3+、Hg2+、Pb2+ 和 Zn2+ 存在下乙腈中 L1-L6 的颜色变化。发现系统 L4-Pb2+、L5-Hg2+ 和 L6-Hg2+ 的选择性减色偏移。对于 L5 和 L6 的 Hg2+ 和 L4 的 Pb2+，观察到最可能与金属与苯胺氮配位相关的发射荧光增强。以铂为工作电极和 [Bu4N][BF4] 作为支持电解质，在乙腈中研究了受体 L1-L6 的电化学行为。该受体家族在 –0.70 V 与 SCE 左右显示
• Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
  作者：Tatiana Ábalos、María Moragues、Santiago Royo、Diego Jiménez、Ramón Martínez‐Máñez、Juan Soto、Félix Sancenón、Salvador Gil、Joan Cano

  DOI：10.1002/ejic.201100834

  日期：2012.1

  modulations in solutions of L1–L6 in acetonitrile in the presence of the metal cations Fe3+, Ni2+, Zn2+, Cd2+, Pb2+ and Hg2+ have been studied. A selective chromogenic response of L4 in the presence of Pb2+ and L5 in the presence of Hg2+ was observed. To get a better insight into the chromophoric nature in the presence of metal cations, the interaction of Hg2+ with the model compound L1 in two different

  已经合成并表征了一系列染料 (L1-L6)，其中包含一个噻唑基基团作为信号亚基和几个具有不同环大小和杂原子类型和数量的大环腔作为结合位点。L1–L6 在乙腈中的溶液在 554–577 nm 范围内显示出宽且无结构的吸收带，典型的摩尔吸收系数范围为 20000 到 32000 M–1 cm–1。使用 L1、L2 和 L5 的乙腈溶液进行了详细的质子化研究。向 L1 和 L2 添加一当量的质子导致分别在 425 和 370 nm 处形成新带，这归因于苯胺氮中的质子化。相比之下，L5 的质子化导致吸收带发生 25 nm 的红移，这在偶氮部分的一个氮原子质子化时是可以想象的。这些结果与 1 H NMR 光谱数据一致。还通过使用密度泛函理论 (DFT) 量子力学计算对模型配体 L1 和不同可能的质子化物质进行了理论研究。已经研究了在金属阳离子 Fe3+、Ni2+、Zn2+、Cd2+、Pb2+ 和 Hg2+
• Universal Dark Quencher Based on “Clicked” Spectrally Distinct Azo Dyes
  作者：Arnaud Chevalier、Julie Hardouin、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1021/ol402972y

  日期：2013.12.6

  The first synthesis of an heterotrifunctional molecular scaffold derived from the popular DABCYL azo dye quencher has been achieved. The sequential derviatization of this trivalent azobenzene derivative with two other nonfluorescent azo dyes (Black Hole Quencher BHQ-1 and BHQ-3) and through effective reactions from the "bioconjugation chemistry" repertoire has led to an universal dark quencher (UDQ). This "clicked" poly azo dye is able to turn off an array of fluorophores covering the UV/NIR (300-750 nm) spectral range.
• Mixed-Ligand Arenechromium Carbonyl Complexes as Electronic Modulators
  作者：Graham B. Jones、Brant J. Chapman、Jude E. Mathews

  DOI：10.1021/jo9721103

  日期：1998.5.1

  A number of mixed ligand eta(6) arenechromium carbonyl complexes have been prepared and investigated for their ability to effect electronic modulation of arene chemistry. In the case of an aniline-derived system, the arenechromium carbonyl complex is able to modulate the inductive capacity of the aniline nitrogen atom and thus, regulate its anchimeric ability. In the case of 8-phenylmenthol and benzyloxazolidinone derivatives, modulation of arene ar basicity is achieved, and results suggest that important vinylarene pi-pi interactions exist in acrylate derivatives of these chiral auxiliary systems.
• Solvent effect and amine interference on colorimetric changes of azobenzene-conjugated dithiaazadioxo crown ether mercury sensor
  作者：Chang Hoon Jeon、Jayeon Lee、Sang Jung Ahn、Tai Hwan Ha

  DOI：10.1016/j.tetlet.2013.10.013

  日期：2013.12

  The colorimetric behavior of an azobenzene-based dye containing dithiaazadioxo ring for Hg2+-detection was investigated in diverse solvents. The mercury specific ligand shows hypsochromic changes in pure and aqueous MeCN upon Hg2+-binding while strong bathochromic shift was observed in chloroform. In both solvent systems, dithiaazadioxo ring is revealed to be indispensable to the selective detection of mercury ion, and several binding schemes in different solvents were proposed on the selective Hg2+ binding. Grafted on cationic polymer (PEI) through amide coupling, it was observed that the ligand basically maintains the Hg2+ detection capability, but substantially hindered by amine moieties in PEI. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.