p-tert-butylcalix[4]arene-mono-propylnalidixate | 1241962-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: p-tert-butylcalix[4]arene-mono-propylnalidixate
• 英文别名: 5,11,17,23-tetra-(tert-butyl)-25-[3-[ω-oxy-propoxycarbonyl]-1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridinyl]-26,27,28-trihydroxycalix[4]arene；3-[(5,11,17,23-Tetratert-butyl-26,27,28-trihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)oxy]propyl 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate；3-[(5,11,17,23-tetratert-butyl-26,27,28-trihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)oxy]propyl 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS: 1241962-96-8
• 化学式: C₅₉H₇₂N₂O₇
• 分子量: 921.23
• InChiKey: JQMKTQQFSLPVFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  68
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 、 bromopropyl nalidixate 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 21.0h， 生成 p-tert-butylcalix[4]arene-mono-propylnalidixate
  参考文献：
  名称：

  Organosoluble calixarene-based quinolone carriers: syntheses, evaluation and model hydrolytic studies at the air–water interface

  摘要：

  作为可能的抗菌原药，合成了两种四对叔丁基和两种四对-H-萼[4]炔化合物，它们的下缘集成了一个或两个萘啶酸丙酯。由于它们具有两亲性，因此使用朗缪尔平衡技术对它们在空气和水界面上的特性进行了评估。结果表明，这两种叔丁基类似物能形成稳定的单层。在对这两种叔丁基类似物进行水解研究之前，先在 20 °C和 37 °C的 pH 值为 10.0 的碳酸盐缓冲底物上对它们进行了研究。研究发现，后者在 37 ° C 下有效，3 天后，双萘啶酸盐衍生物的游离萘啶酸盐生成率为 13%，单萘啶酸盐的生成率为 10%。

  DOI：

  10.1039/c1nj20636b

文献信息

• The Mechanism of Metal Cation Binding in Two Nalidixate Calixarene Conjugates. A Langmuir Film and Molecular Modeling Study
  作者：Beata Korchowiec、Monika Orlof、Guillaume Sautrey、Adel Ben Salem、Jacek Korchowiec、Jean-Bernard Regnouf-de-Vains、Ewa Rogalska

  DOI：10.1021/jp102471c

  日期：2010.8.19

  The two new p-tert-butylcalix[4]arene derivatives described here bear one or two nalidixic acid arms linked to the lower calixarene rim via the quinolone carboxylate moiety. These derivatives were synthesized in order to investigate two important features of molecules conceived as potential antibiotics, namely, metal cation complexation and interfacial properties, and the way in which they interrelate. The properties of the calixarene derivatives were studied in monomolecular films spread on pure water and on aqueous subphases containing biologically relevant mono- and divalent metal cations. These systems were examined via surface pressure and surface electrical potential measurements, polarization modulation infrared reflection absorption spectroscopy, and molecular modeling. Molecular modeling shows that important differences exist, first, between the structure and stability of the complexes formed with the two derivatives and, second, between their mono- and dication complexes. Correlating the properties of the monolayers with those of the modeled molecules lets its propose that the derivatives bearing one or two nalidixic pending arms form preferentially inter- and intramolecular complexes, respectively. The results obtained in this study indicate that a possible biological role of the nalidixic arms grafted on the calixarene crown may be revealed upon cation complexation.
• Organosoluble calixarene-based quinolone carriers: syntheses, evaluation and model hydrolytic studies at the air–water interface
  作者：Guillaume Sautrey、Igor Clarot、Adel Ben Salem、Ewa Rogalska、Jean-Bernard Regnouf de Vains

  DOI：10.1039/c1nj20636b

  日期：——

  Two tetra-p-tert-butyl- and two tetra-p-H-calix[4]arene species integrating one or two propylnalidixate esters at the lower rim have been synthesized as possible antibacterial prodrugs. As they display amphiphilic behavior, their properties at the air–water interface were evaluated using the Langmuir balance technique. It has been shown that the two tert-butyl analogues form stable monolayers. The two tert-butyl analogues were then studied at 20 and 37 °C on carbonate buffered subphases at pH 10.0, before being engaged in hydrolytic studies on “production” of monolayers so as to allow a simple treatment, a HPLC survey of nalidixate release. The latter was found to be effective at 37 °C, with formation of free nalidixate in 13% yield for the bisnalidixate derivative, and 10% yield for the mononalidixate after 3 days.

  作为可能的抗菌原药，合成了两种四对叔丁基和两种四对-H-萼[4]炔化合物，它们的下缘集成了一个或两个萘啶酸丙酯。由于它们具有两亲性，因此使用朗缪尔平衡技术对它们在空气和水界面上的特性进行了评估。结果表明，这两种叔丁基类似物能形成稳定的单层。在对这两种叔丁基类似物进行水解研究之前，先在 20 °C和 37 °C的 pH 值为 10.0 的碳酸盐缓冲底物上对它们进行了研究。研究发现，后者在 37 ° C 下有效，3 天后，双萘啶酸盐衍生物的游离萘啶酸盐生成率为 13%，单萘啶酸盐的生成率为 10%。