5,17-bis(3-nitrophenyl)-25,27-bis(hydroxycarbonylmethoxy)calix[4]arene-26,28-diol | 514204-20-7

• 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: 5,17-bis(3-nitrophenyl)-25,27-bis(hydroxycarbonylmethoxy)calix[4]arene-26,28-diol
• 英文别名: 2-[[27-(Carboxymethoxy)-26,28-dihydroxy-5,17-bis(3-nitrophenyl)-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]oxy]acetic acid
• CAS: 514204-20-7
• 化学式: C₄₄H₃₄N₂O₁₂
• 分子量: 782.76
• InChiKey: XDHJZNKHKXYMDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  225
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,17-bis(3-nitrophenyl)-25,27-bis(hydroxycarbonylmethoxy)calix[4]arene-26,28-diol 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 33.0h， 生成 5-(3-aminophenyl)-17-(3-nitrophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol
  参考文献：
  名称：

  Host−[2]Rotaxane:  Advantage of Converging Functional Groups for Guest Recognition

  摘要：

  A host-[2]rotaxane was constructed by converting a diaminophenylcalix[4]arene into a [2]rotaxane using the DCC-rotaxane method (Zehnder, D.; Smithrud, D. B. Org. Lett. 2001, 16, 2485-2486). N-Ac-Arg groups were attached to the dibenzo-24-crown-8 ring of the rotaxane to provide a convergent functional group. To demonstrate the advantage provided by the rotaxane architecture for recognition of guests that contain a variety of functional groups, association constants (K-A) for N-Ac-Trp, indole, N-Ac-Gly, fluorescein, 1-(dimethylamino)-5-naphthalenesulfonate, and pyrene bound to the [2]rotaxane were determined by performing H-1 NMR and fluorescence spectroscopic experiments. The host-[2]rotaxane had the highest affinity for fluorescein with a K-A = 4.6 x 106 M-1 in a 98/2 buffer (1 mM phosphate, pH 7)/DMSO solution. A comparison of K-A values demonstrates that both the aromatic pocket and ring of the host-[2]rotaxane contribute binding free energy for complexation. Association constants were also derived for the same guests bound to the diaminophenylcalix[4]arene and to a diphenylcalix[4]arene that contained arginine residues displayed in a nonconvergent fashion. The host-[2]rotaxane provides higher affinity and specificity for most guests than the host with divergent N-Ac-Arg groups of the one that only has an aromatic pocket. For example, the K-A for the complex of the host-[2]rotaxane and fluorescein in the DMSO/water mixture is more than 2 orders of magnitude greater than association constants derived for the other hosts.

  DOI：

  10.1021/jo026522+
• 作为产物：
  描述：

  杯[4]芳烃 在 四(三苯基膦)钯 、 溴 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 43.0h， 生成 5,17-bis(3-nitrophenyl)-25,27-bis(hydroxycarbonylmethoxy)calix[4]arene-26,28-diol
  参考文献：
  名称：

  Host−[2]Rotaxane:  Advantage of Converging Functional Groups for Guest Recognition

  摘要：

  A host-[2]rotaxane was constructed by converting a diaminophenylcalix[4]arene into a [2]rotaxane using the DCC-rotaxane method (Zehnder, D.; Smithrud, D. B. Org. Lett. 2001, 16, 2485-2486). N-Ac-Arg groups were attached to the dibenzo-24-crown-8 ring of the rotaxane to provide a convergent functional group. To demonstrate the advantage provided by the rotaxane architecture for recognition of guests that contain a variety of functional groups, association constants (K-A) for N-Ac-Trp, indole, N-Ac-Gly, fluorescein, 1-(dimethylamino)-5-naphthalenesulfonate, and pyrene bound to the [2]rotaxane were determined by performing H-1 NMR and fluorescence spectroscopic experiments. The host-[2]rotaxane had the highest affinity for fluorescein with a K-A = 4.6 x 106 M-1 in a 98/2 buffer (1 mM phosphate, pH 7)/DMSO solution. A comparison of K-A values demonstrates that both the aromatic pocket and ring of the host-[2]rotaxane contribute binding free energy for complexation. Association constants were also derived for the same guests bound to the diaminophenylcalix[4]arene and to a diphenylcalix[4]arene that contained arginine residues displayed in a nonconvergent fashion. The host-[2]rotaxane provides higher affinity and specificity for most guests than the host with divergent N-Ac-Arg groups of the one that only has an aromatic pocket. For example, the K-A for the complex of the host-[2]rotaxane and fluorescein in the DMSO/water mixture is more than 2 orders of magnitude greater than association constants derived for the other hosts.

  DOI：

  10.1021/jo026522+

文献信息

• Compositions and methods for targeted drug delivery
  申请人：Smithrud B. David

  公开号：US20070027075A1

  公开（公告）日：2007-02-01

  The present invention provides for methods and compositions for transporting agents and macromolecules across biological membranes. In one embodiment, the invention relates to a method for enhancing transport of a selected agent across a biological membrane, wherein a biological membrane is contacted with a composition containing a biologically active rotaxane capable of selectively transporting the selected agent. The host-rotaxane is effective to impart to the agent an amount transport and/or rate of trans-membrane transport across a biological membrane that is greater than the amount and/or rate of trans-membrane transport of the agent without the host-rotaxane.
• [EN] COMPOSITIONS AND METHODS FOR TARGETED DRUG DELIVERY<br/>[FR] COMPOSITIONS ET METHODES POUR ADMINISTRATION CIBLEE DE MEDICAMENTS
  申请人：UNIV CINCINNATI

  公开号：WO2005004795A2

  公开（公告）日：2005-01-20

  [EN] The present invention provides for methods and compositions for transporting agents and macromolecules across biological membranes. In one embodiment, the invention relates to a method for enhancing transport of a selected agent across a biological membrane, wherein a biological membrane is contacted with a composition containing a biologically active rotaxane capable of selectively transporting the selected agent. The host-rotaxane is effective to impart to the agent an amount transport and/or rate of trans-membrane transport across a biological membrane that is greater than the amount and/or rate of trans-membrane transport of the agent without the host-rotaxane.
  [FR] La présente invention concerne des méthodes et des compostions pour le transport d'agents et de macromolécules au travers de membranes biologiques. Dans un mode de réalisation, l'invention concerne une méthode propre à favoriser le transport d'un agent donné au travers d'une membrane biologique, ladite membrane étant mise en contact avec un une composition qui contient un carénante biologiquement active capable de transporteur sélectivement ledit agent. Le caténane-hôte permet d'appliquer à l'agent à l'agent une impulsion de transport et/ou un taux de transport trans-membranaire à travers une membrane biologique qui sont supérieurs à ce qu'ils sont sans emploi d'un caténane hôte.
• Host−[2]Rotaxane:  Advantage of Converging Functional Groups for Guest Recognition
  作者：Inese Smukste、Brian E. House、David B. Smithrud

  DOI：10.1021/jo026522+

  日期：2003.4.1

  A host-[2]rotaxane was constructed by converting a diaminophenylcalix[4]arene into a [2]rotaxane using the DCC-rotaxane method (Zehnder, D.; Smithrud, D. B. Org. Lett. 2001, 16, 2485-2486). N-Ac-Arg groups were attached to the dibenzo-24-crown-8 ring of the rotaxane to provide a convergent functional group. To demonstrate the advantage provided by the rotaxane architecture for recognition of guests that contain a variety of functional groups, association constants (K-A) for N-Ac-Trp, indole, N-Ac-Gly, fluorescein, 1-(dimethylamino)-5-naphthalenesulfonate, and pyrene bound to the [2]rotaxane were determined by performing H-1 NMR and fluorescence spectroscopic experiments. The host-[2]rotaxane had the highest affinity for fluorescein with a K-A = 4.6 x 106 M-1 in a 98/2 buffer (1 mM phosphate, pH 7)/DMSO solution. A comparison of K-A values demonstrates that both the aromatic pocket and ring of the host-[2]rotaxane contribute binding free energy for complexation. Association constants were also derived for the same guests bound to the diaminophenylcalix[4]arene and to a diphenylcalix[4]arene that contained arginine residues displayed in a nonconvergent fashion. The host-[2]rotaxane provides higher affinity and specificity for most guests than the host with divergent N-Ac-Arg groups of the one that only has an aromatic pocket. For example, the K-A for the complex of the host-[2]rotaxane and fluorescein in the DMSO/water mixture is more than 2 orders of magnitude greater than association constants derived for the other hosts.