5,17-bis(3-aminophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol | 514204-23-0

• 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-aminophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol
• 英文别名: Methyl 2-[[5,17-bis(3-aminophenyl)-26,28-dihydroxy-27-(2-methoxy-2-oxoethoxy)-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]acetate
• CAS: 514204-23-0
• 化学式: C₄₆H₄₂N₂O₈
• 分子量: 750.848
• InChiKey: WYDWBKJAYMECCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  164
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Boc-Arg(Boc)2OH 、 5,17-bis(3-aminophenyl)-25,27-bis(methoxycarbonylmethoxy)calix[4]arene-26,28-diol 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以84%的产率得到methyl 2-[[5,17-bis[3-[[(2S)-5-[[(Z)-N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]phenyl]-26,28-dihydroxy-27-(2-methoxy-2-oxoethoxy)-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]acetate
  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：

  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 5,17-bis(3-aminophenyl)-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+

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.
• 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.