1,4,10,13-四氧杂-7,16-二氮杂环十八烷,7,16-二十四烷基- | 105400-07-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,4,10,13-四氧杂-7,16-二氮杂环十八烷,7,16-二十四烷基-
• 英文名称: N,N'-ni-n-tetradecyl-4,13-diaza-18-crown-6
• 英文别名: 7,16-Di(tetradecyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 105400-07-5
• 化学式: C₄₀H₈₂N₂O₄
• 分子量: 655.102
• InChiKey: YMQRSZKTOGVGAO-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C(Solv: hexane (110-54-3))
• 沸点：
  695.4±50.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  肉豆蔻酸 在 氯化亚砜 、 sodium carbonate 、 diborane(6) 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 55.0h， 生成 1,4,10,13-四氧杂-7,16-二氮杂环十八烷,7,16-二十四烷基-
  参考文献：
  名称：

  Syntheses and binding properties of bibrachial lariat ethers (BiBLEs): survey of synthetic methods and cation selectivities

  摘要：

  DOI：

  10.1021/jo00376a059

文献信息

• Supramolecular cation transporters alter root morphology in the Arabidopsis thaliana plant
  作者：Mohit B. Patel、Saeedeh Negin、Ariel Stavri、George W. Gokel

  DOI：10.1016/j.ica.2017.05.019

  日期：2017.11

  (two-armed) 4,13-diaza-18-crown-6 lariat ether and tris (macrocycle) hydraphile synthetic amphiphiles alter root morphology in Arabidopsis thaliana plants. The effect on root structure and growth depends both on the hydraphile spacer chain length and lariat ether side chain length as well as the concentration of compound in the growth medium. In some cases a correlation to ion transport activity was apparent

  摘要Bibracchial（两臂）4,13-diaza-18-crown-6套索状醚和tris（大环）亲水性两亲物改变了拟南芥植物的根系形态。对根结构和生长的影响取决于亲水间隔基链长度和套索状醚侧链长度，以及生长培养基中化合物的浓度。在某些情况下，与离子迁移活性的相关性很明显，但是这种相关性并不总是很明显。出乎意料的是，平面双层电导（BLM）研究表明套索醚和套索醚酰胺均表现出良好的膜活性控制能力。大豆asolectin膜中的孔形成很容易发生，并且孔稳定且持续。低浓度的活性亲水物和套索状醚改变了初级：侧根的密度比，通常会增加它。转运蛋白介导的侧根密度的改变暗示了植物生长素的活性，例如吲哚-3-乙酸和2,4-二氯苯氧基乙酸，它们依赖于胞质钾离子浓度。通过使用抗生长素的拟南芥突变体，测试并消除了化合物干扰生长素途径的假说。离子载体不是直接充当生长素模拟物，而是会影响离子梯度，从而对根的发育产生类
• Re-evaluation of the mechanism of cytotoxicity of dialkylated lariat ether compounds
  作者：Willy Carrasquel-Ursulaez、Ryan D. Reeves、Mahzad Dehghany、Corey Jones、Jennifer M. Schomaker、Baron Chanda

  DOI：10.1039/d0ra08494h

  日期：——

  The cytotoxicity of dialkylated lariat ethers has been previously attributed to their ionophoric properties. Herein, we provide evidence that these effects are due to loss of membrane integrity rather than ion transport, a finding with important implications for the future design of synthetic ionophores.

  二烷基化套索醚的细胞毒性先前已归因于它们的离子载体特性。在这里，我们提供的证据表明这些影响是由于膜完整性的丧失而不是离子传输，这一发现对合成离子载体的未来设计具有重要意义。
• Correlation of bilayer membrane cation transport and biological activity in alkyl-substituted lariat ethers
  作者：W. Matthew Leevy、Michelle E. Weber、Michael R. Gokel、George B. Hughes-Strange、David D. Daranciang、Riccardo Ferdani、George W. Gokel

  DOI：10.1039/b418194h

  日期：——

  Dialkyldiaza-18-crown-6 lariat ethers having twin n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, 1-oxodecyl and 1-oxododecyl side arms were prepared and studied. Cation transport in liposomes mediated by these compounds showed discontinuous activity that correlated with toxicity to the bacteria E. coli and B. Subtilis, and the yeast S. Cerevisiae. Transport, toxicity and membrane depolarization studies all suggest that side chain length affords very different interactions in a bilayer membrane compared with bulk phases. An explanation for activity in terms of carrier transport and restricted transverse relaxation is proposed.

  制备并研究了具有双正辛基、正癸基、正十二烷基、正十四烷基、正十六烷基、1-氧代癸基和1-氧代十二烷基侧臂的二烷基二氮杂-18-冠-6型络合物。这些化合物介导的脂质体中的阳离子转运表现出不连续活性，这与对大肠杆菌、枯草芽孢杆菌和酿酒酵母的毒性相关。转运、毒性和膜去极化研究均表明，侧链长度在双层膜中的相互作用与在整体相中的相互作用截然不同。提出了以载体转运和受限横向弛豫来解释活性的方法。
• Molecules that inhibit efflux pumps in multi-drug resistant bacteria and uses thereof
  申请人：The Curators of the University of Missouri

  公开号：US10463044B2

  公开（公告）日：2019-11-05

  Methods and compositions are provided for increasing or enhancing the efficacy of antibiotics, such as by increasing antimicrobial activity, against a variety of microbes by co-administration with synthetic amphiphiles, including lariat ethers and hydraphiles. Methods and compositions for overcoming antibiotic resistance are also provided.

  提供了通过与合成双亲化合物（包括长链醚和水合化合物）共同施用来提高或增强抗生素疗效的方法和组合物，例如通过提高抗菌活性来对抗各种微生物。此外，还提供了克服抗生素耐药性的方法和组合物。
• Enhancement of antibiotic efficacy
  申请人：The Curators of the University of Missouri

  公开号：US10791740B2

  公开（公告）日：2020-10-06

  Methods and compositions are provided for increasing or enhancing the efficacy of antibiotics, such as by increasing antimicrobial activity, against a variety of microbes by co-administration with synthetic amphiphiles, including lariat ethers and hydraphiles. Methods and compositions for overcoming antibiotic resistance are also provided.

  提供了通过与合成双亲化合物（包括长链醚和水合化合物）共同施用来提高或增强抗生素疗效的方法和组合物，例如通过提高抗菌活性来对抗各种微生物。此外，还提供了克服抗生素耐药性的方法和组合物。